- Formation of protein charge ladders by acylation of amino groups on proteins
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The values of charge and electrophoretic mobility of a protein are changed upon acylation of its α- and Lys ε-NH3+ groups. Partial acylation of the amino groups of a protein results in a set of derivatives that is often resolved by c
- Colton, Ian J.,Anderson, Janelle R.,Gao, Jinming,Chapman, Robert G.,Isaacs, Lyle,Whitesides, George M.
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Read Online
- Synthesis, incorporation efficiency, and stability of disulfide bridged functional groups at RNA 5'-ends
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Modified guanosine monophosphates have been employed to introduce various functional groups onto RNA 5'-ends. Applications of modified RNA 5'-ends include the generation of functionalized RNA libraries for in vitro selection of catalytic RNAs, the attachm
- Sengle, Gerhard,Jenne, Andreas,Arora, Paramjit S.,Seelig, Burckhard,Nowick, James S.,Jaeschke, Andres,Famulok, Michael
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Read Online
- Preparation of N-hydroxysuccinimido esters via palladium-catalyzed carbonylation of aryl triflates and halides
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N-Hydroxysuccinimido esters of aromatic carboxylic acids (a.k.a. active esters) can be made using a potentially general, one-step procedure via Pd-catalyzed carbonylation of an aryl triflate or aryl iodide with CO and N-hydroxysuccinimide. Excellent yields (up to 94%) were observed when the reaction was done in DMSO at 70°C and 1 atmosphere of CO pressure.
- Lou, Rongliang,VanAlstine, Melissa,Sun, Xufeng,Wentland, Mark P.
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Read Online
- Eight-membered ring-containing jadomycins: Implications for non-enzymatic natural products biosynthesis
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Jadomycin Oct (1) was isolated from Streptomyces venezuelae ISP5230 and characterized as a structurally unique eight-membered l-ornithine ring-containing jadomycin. The structure was elucidated through the semisynthetic derivatization of starting material via chemoselective acylation of the l-ornithine α-amino group using activated succinimidyl esters. Incorporation of 5-aminovaleric acid led to jadomycin AVA, a second eight-membered ring-containing jadomycin. These natural products illustrate the structural diversity permissible from a non-enzymatic step within a biosynthetic pathway and exemplifies the potential for discovery of novel scaffolds.
- Robertson, Andrew W.,Martinez-Farina, Camilo F.,Smithen, Deborah A.,Yin, Huimin,Monro, Susan,Thompson, Alison,McFarland, Sherri A.,Syvitski, Raymond T.,Jakeman, David L.
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Read Online
- Development of succinimide-based inhibitors for the mitochondrial rhomboid protease PARL
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While the biochemistry of rhomboid proteases has been extensively studied since their discovery two decades ago, efforts to define the physiological roles of these enzymes are ongoing and would benefit from chemical probes that can be used to manipulate the functions of these proteins in their native settings. Here, we describe the use of activity-based protein profiling (ABPP) technology to conduct a targeted screen for small-molecule inhibitors of the mitochondrial rhomboid protease PARL, which plays a critical role in regulating mitophagy and cell death. We synthesized a series of succinimide-containing sulfonyl esters and sulfonamides and discovered that these compounds serve as inhibitors of PARL with the most potent sulfonamides having submicromolar affinity for the enzyme. A counterscreen against the bacterial rhomboid protease GlpG demonstrates that several of these compounds display selectivity for PARL over GlpG by as much as two orders of magnitude. Both the sulfonyl ester and sulfonamide scaffolds exhibit reversible binding and are able to engage PARL in mammalian cells. Collectively, our findings provide encouraging precedent for the development of PARL-selective inhibitors and establish N-[(arylsulfonyl)oxy]succinimides and N-arylsulfonylsuccinimides as new molecular scaffolds for inhibiting members of the rhomboid protease family.
- Andrews, Charlotte L.,Cardozo, Joaquin M.,Chow, Alyssa S.,Crainic, Jennifer A.,Parsons, William H.,Rutland, Nicholas T.,Sheehan, Brendan K.
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supporting information
(2021/08/04)
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- N -Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N -hydroxysuccinimide ester formation
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A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which facilely converted into amides in one pot. In addition, the drug moclobemide was synthesized to represent the practical utility of the developed methodology. This journal is
- Singh, Ashmita,Narula
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supporting information
p. 7486 - 7490
(2021/05/13)
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- Formation of 1-hydroxymethylene-1,1-bisphosphinates through the addition of a silylated phosphonite on various trivalent derivatives
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An easily handled one-pot synthetic procedure was previously developed for the synthesis of bisphosphinates starting from acyl chlorides. Herein, other trivalent derivatives as acid anhydrides and activated esters were tested to form various bisphosphinates. This modulation of the reactivity can be controlled according to the nature of the acid derivative for the use of sensitive and functionalized substrates.
- Dussart-Gautheret, Jade,Deschamp, Julia,Monteil, Maelle,Gager, Olivier,Legigan, Thibaut,Migianu-Griffoni, Evelyne,Lecouvey, Marc
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p. 14559 - 14569
(2020/12/29)
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- CHEMOSELECTIVE SENSITIVITY BOOSTER FOR TAGGING A PEPTIDE, PEPTIDE CONJUGATE, OR SIMILAR REACTIVE MOLECULE
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The invention pertains to chemoselective sensitivity booster for tagging a peptide, peptide conjugate, or similar reactive molecule for analysis of a peptide, protein, antibody, protein bioconjugate, antibody bioconjugate, and similar analytes. The sensitivity booster comprises of sp2 or sp3 nitrogen centers in combination with hydrophobic carbon chains linked with an electrophile or nucleophile for attachment with a peptide, peptide conjugate, or molecules with similar reactivity.
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Page/Page column 39
(2020/12/29)
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- Argininamide-type neuropeptide y Y1 receptor antagonists: The nature of: N Ω-carbamoyl substituents determines Y1R binding mode and affinity
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The recently resolved crystal structure of the neuropeptide Y Y1 receptor (Y1R), co-crystallized with the high-affinity (pKi: 10.11), argininamide-type Y1R antagonist UR-MK299 (2), revealed that the NΩ-carbamoyl substituent (van der Waals volume: 139 ?3) is deeply buried in the receptor, occupying a hydrophobic pocket. We synthesized and characterized a series of argininamides, structurally related to 2. Y1R affinity decreased with increasing size of the carbamoyl residue (minimal pKi: 5.67). Exceeding a critical size of the substituent (van der Waals volume: 212 ?3), the ligands bound in an inverted mode with the carbamoyl side chain located at the surface of the receptor, as suggested by induced-fit docking and MD simulations.
- Buschmann, Jonas,Keller, Max,Seiler, Theresa,Wifling, David,Bernhardt, Günther
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supporting information
p. 274 - 282
(2020/04/17)
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- Ynamide-Mediated Thionoester and Dithioester Syntheses
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A novel ynamide-mediated synthesis of thionoesters and dithioesters is described. The selective addition reactions of various monothiocarboxylic acids with ynamide furnish α-thioacyloxyenamides, which undergo transesterification with nucleophilic -OH or -SH species to afford thionoesters and dithioesters, respectively. The broad substrate scope, mild reaction conditions, and excellent yields make this method an attractive synthetic approach to thionoesters and dithioesters.
- Yao, Chaochao,Yang, Jinhua,Lu, Xiaobiao,Zhang, Shuyu,Zhao, Junfeng
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supporting information
p. 6628 - 6631
(2020/09/02)
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- Halide-Accelerated Acyl Fluoride Formation Using Sulfuryl Fluoride
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Herein, we report a new one-pot sequential method for SO2F2-mediated nucleophilic acyl substitution reactions starting from carboxylic acids. A mechanistic study revealed that SO2F2-mediated acid activation proceeds via the anhydride, which is then converted to the corresponding acyl fluoride. Tetrabutylammonium chloride or bromide accelerate the formation of acyl fluoride. Optimized halide-accelerated conditions were used to synthesize acyl fluorides in 30-80percent yields, and esters, amides, and thioesters in 72-96percent yields without reoptimization for each nucleophile.
- Foth, Paul J.,Malig, Thomas C.,Yu, Hao,Bolduc, Trevor G.,Hein, Jason E.,Sammis, Glenn M.
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supporting information
p. 6682 - 6686
(2020/09/02)
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- N-Doped Yellow TiO2 Hollow Sphere-Mediated Visible-Light-Driven Efficient Esterification of Alcohol and N-Hydroxyimides to Active Esters
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Herein we report a simple synthetic protocol for N-doped yellow TiO2 (N-TiO2) hollow spheres as an efficient visible-light-active photocatalyst using aqueous titanium peroxocarbonate complex (TPCC) solution as precursor and NH4OH. In the developed strategy, the ammonium ion of TPCC and NH4OH acts as nitrogen source and structure-directing agent. The synthesized N-TiO2 hollow spheres are capable of promoting the synthesis of active esters of N-hydroxyimide and alcohol through simultaneous selective oxidation of alcohol to aldehyde followed by cross-dehydrogenative coupling (CDC) under ambient conditions upon irradiation of visible light. It is possible to develop a novel and cost-effective one-pot strategy for the synthesis of important esters and amides on gram scale using the developed strategy. The catalytic activity of N-TiO2 hollow spheres is much superior to that of other reported N-TiO2 samples as well as TiO2 with varying morphology.
- Singha, Krishnadipti,Ghosh, Subhash Ch.,Panda, Asit Baran
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p. 3205 - 3212
(2019/09/09)
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- Sensitivity booster for mass detection enables unambiguous analysis of peptides, proteins, antibodies, and protein bioconjugates
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A chemical tag enhances peptide detection by multiple orders in mass spectrometry. The substantial improvement in the peptide mapping along with simplified and enhanced fragmentation pattern enables the unambiguous sequencing of a protein and antibody. The chemoselective sensitivity booster provides a tool for remarkably improved analysis of protein bioconjugates.
- Singudas, Rohith,Reddy, Neelesh C.,Rai, Vishal
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supporting information
p. 9979 - 9982
(2019/08/22)
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- Regioselective microwave synthesis and derivatization of 1,5-diaryl-3-amino-1,2,4-triazoles and a study of their cholinesterase inhibition properties
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Herein we describe the development of an efficient one-pot regioselective synthesis protocol to obtain N-protected or N-deprotected 1,5-diaryl-3-amino-1,2,4-triazoles from N-acyl-N-Boc-carbamidothioates. This improved protocol using microwave irradiation and low reaction times (up to 1 h) furnished desired compounds in yields ranging from 50 to 84%. This chemistry is useful for a variety of aromatic groups with electronically diverse substituents. The design and correct derivation of the amino group led to compounds able to inhibit cholinesterases with good IC50 of up to 1 μM. Also, the mode of action (mixed-type) and SAR analysis for this series of compounds was described by means of kinetic and molecular modelling evaluations, showing potential for this class of compounds as new scaffolds for this biological activity.
- Santos, Sabrina Neves,Alves De Souza, Gabriela,Pereira, Thiago Moreira,Franco, Daiana Portella,De Nigris Del Cistia, Catarina,Sant'anna, Carlos Mauricio R.,Lacerda, Renata Barbosa,Kümmerle, Arthur Eugen
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p. 20356 - 20369
(2019/07/09)
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- RADIOLABELED DRUG
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The present invention relates to a compound, etc. capable of providing a radiolabeled drug that can reduce the renal accumulation thereof in the early stage after the administration thereof. [1] A compound, etc. represented by the formula (1), [2] a compo
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Paragraph 0205; 0206; 0207; 0208
(2019/04/14)
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- Impact of Molecular Architecture and Adsorption Density on Adhesion of Mussel-Inspired Surface Primers with Catechol-Cation Synergy
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Marine mussels secrete proteins rich in residues containing catechols and cationic amines that displace hydration layers and adhere to charged surfaces under water via a cooperative binding effect known as catechol-cation synergy. Mussel-inspired adhesives containing paired catechol and cationic functionalities are a promising class of materials for biomedical applications, but few studies address the molecular adhesion mechanism(s) of these materials. To determine whether intramolecular adjacency of these functionalities is necessary for robust adhesion, a suite of siderophore analog surface primers was synthesized with systematic variations in intramolecular spacing between catechol and cationic functionalities. Adhesion measurements conducted with a surface forces apparatus (SFA) allow adhesive failure to be distinguished from cohesive failure and show that the failure mode depends critically on the siderophore analog adsorption density. The adhesion of these molecules to muscovite mica in an aqueous electrolyte solution demonstrates that direct intramolecular adjacency of catechol and cationic functionalities is not necessary for synergistic binding. However, we show that increasing the catechol-cation spacing by incorporating nonbinding domains results in decreased adhesion, which we attribute to a decrease in the density of catechol functionalities. A mechanism for catechol-cation synergy is proposed based on electrostatically driven adsorption and subsequent binding of catechol functionalities. This work should guide the design of new adhesives for binding to charged surfaces in saline environments.
- Degen, George D.,Stow, Parker R.,Lewis, Robert B.,Andresen Eguiluz, Roberto C.,Valois, Eric,Kristiansen, Kai,Butler, Alison,Israelachvili, Jacob N.
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supporting information
p. 18673 - 18681
(2019/11/28)
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- A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides by a TiO2-Co ascorbic acid nanohybrid under visible light irradiation
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In this study, we performed a visible light-mediated aerobic photo-cross dehydrogenative coupling (CDC) reaction between aldehydes and N-hydroxyimides using TiO2-AA-Co as a photocatalyst for the synthesis of active esters. The synergistic and selective effects of the cobalt ascorbic acid complex (Co-AA) and TiO2 nanoparticles on the visible-light photocatalytic activity were explored. The method possesses some advantages such as environmentally friendly conditions, easy work-up procedure, reusability, and scalability.
- Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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supporting information
p. 807 - 811
(2018/02/06)
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- Preparation method and application of benzamide derivative
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The invention discloses a preparation method and application of a benzamide derivative as shown in a formula (I) which is described in the specification. The objective of the invention is to improve the chelation stability of zinc ions of histone deacetylase in the prior art so as to obtain HDACi with better histone deacetylase inhibition effect and stronger selectivity. The derivative provided bythe invention can be applied to preparation of antitumor drugs and is capable of improving the capability of HDACi in selection of a part of tumor cells and substantially reducing cytotoxicity.
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Paragraph 0014
(2018/05/07)
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- IMMEDIATE-RELEASE ABUSE DETERRENT COMPOSITIONS OR MEDICAMENTS FOR TREATING PAIN, ADD, ADHD AND OTHER SYNDROMES OR DISORDERS
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The presently described technology provides one or more compositions, preferably one or more immediate-release profile compositions, comprising aryl carboxylic acids chemically conjugated to hydrocodone (morphinan-6-one, 4,5- alpha-epoxy-3-methoxy-17-meth
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- Atmospheric oxidative catalyst-free cross-dehydrogenative coupling of aldehydes with N-hydroxyimides
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Cross-dehydrogenative coupling (CDC) reactions of aldehydes with N-hydroxyimidates such as N-hydroxysuccinimide (NHSI), N-hydroxyphthalimide (NHPI) under catalyst-free conditions is described. Moreover, the desired products can be obtained simply by recrystallization from ethanol. This method is also applicable to the synthesis of amides in excellent yields. A radical mechanism of the type shown in Scheme 4 is proposed based upon the inhibition of the reaction in the presence of TEMPO.
- Xu, Xiaohe,Li, Pingping,Huang, Yingyi,Tong, Chuo,Yan, YiYan,Xie, Yuanyuan
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supporting information
p. 1742 - 1746
(2017/04/13)
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- Design, synthesis and structure-activity relationship studies of a novel focused library of 2,3,4-substituted oxazolidines with antiproliferative activity against cancer cell lines
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In the present work we describe the synthesis and antiproliferative evaluation of a focused library of 30 novel oxazolidines designed by modification of N-substituent, by ring variation, by alkyl variation or by extension of the structure. It was noted that carbamate and N,O-aminal groups were essential for activity. In general, replacement of the phenyl ring with pyridinyl was not tolerated. However, the introduction of a second phenyl ring with an appropriate spacer at the 3- or 4-position of the first phenyl ring generally enhanced the cytotoxic profile. Among all the prepared compounds, 24 was the most potent compound found in this class, being active on four of five cancer cell lines and it was 5-fold and 10-fold more potent than the lead compounds against HL60 and JURKAT cells, respectively. In addition, it showed relevant activity against MCF-7 and HCT-116 cells, which were resistant to lead. Moreover, 24 showed little antiproliferative activity against VERO, indicating low toxicity to normal cells. Thus, this compound has the potential to be developed as an anticancer agent.
- Andrade, Saulo F.,Oliveira, Bárbara G.,Pereira, Larissa C.,Ramos, Jonas P.,Joaquim, Angélica R.,Steppe, Martin,Souza-Fagundes, Elaine M.,Alves, Ricardo J.
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- General method for the preparation of active esters by palladium-catalyzed alkoxycarbonylation of aryl bromides
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A useful method was developed for the synthesis of active esters by palladium-catalyzed alkoxycarbonylation of (hetero)aromatic bromides. The protocol was general for a range of oxygen nucleophiles including N-hydroxysuccinimide (NHS), pentafluorophenol (PFP), hexafluoroisopropyl alcohol (HFP), 4-nitrophenol, and N-hydroxyphthalimide. A high functional group tolerance was displayed, and several active esters were prepared with good to excellent isolated yields. The protocol was extended to access an important synthetic precursor to the HIV-protease inhibitor, saquinavir, by formation of an NHS ester followed by acyl substitution.
- De Almeida, Angelina M.,Andersen, Thomas L.,Lindhardt, Anders T.,De Almeida, Mauro V.,Skrydstrup, Troels
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supporting information
p. 1920 - 1928
(2015/02/19)
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- Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate
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An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)2/Xantphos catalyst system.
- Barré, Ana?s,T?nta?, Mihaela-Liliana,Alix, Florent,Gembus, Vincent,Papamica?l, Cyril,Levacher, Vincent
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supporting information
p. 6537 - 6544
(2015/10/05)
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- Cross dehydrogenative coupling (CDC) of aldehydes with N-hydroxyimides by visible light photoredox catalysis
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A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides has been developed for the synthesis of ester derivatives. Using 2 mol% [Ru(bpy)3]Cl2 in dry acetonitrile at room temperature with an LED light bulb, we were able to synthesize N-hydroxyesters in good yields. The ester derivatives are very useful synthetic intermediates, which were transformed to amide and oxazole building blocks in excellent yields. This journal is
- Dinda, Milan,Bose, Chandan,Ghosh, Tridev,Maity, Soumitra
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p. 44928 - 44932
(2015/06/02)
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- Benzoic Acid, Benzoic Acid Derivatives and Heteroaryl Carboxylic Acid Conjugates of Hydrocodone, Prodrugs, Methods of Making and Use Thereof
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The presently described technology provides methods of treating a patient having moderate to severe pain, narcotic or opioid abuse or narcotic or opioid withdrawal. The presently described methods are carried out by comprising administering to the patient
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- A very mild and selective method for O-benzoylation of hydroxamic acids
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Selective O-benzoylation of hydroxamic acids is achieved by the treatment of BPO and DABCO. Aliphatic alcohols are not reactive under these conditions. Various radical or oxidation sensitive functional groups are compatible with this protocol, and no anhydrous reagents or solvents are required for the high yields of the benzoylations.
- Zheng, Yongsheng,Liu, Muqiong,Yuan, Yu
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supporting information
p. 4404 - 4406
(2014/07/22)
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- One-pot synthesis of hydroxamic acids from aldehydes and hydroxylamine
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A one-pot oxidative transformation of aldehydes into hydroxamic acids by the use of an aqueous solution of hydroxylamine is reported. The methodology gives high yields and makes use of cheap, abundant and easily available reagents.
- Dettori, Giovanna,Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
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supporting information
p. 2709 - 2713
(2014/09/17)
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- Relative quantitation of glycopeptides based on stable isotope labeling using MALDI-TOF MS
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We have developed an effective, sensitive method for quantitative glycopeptide profiling using stable isotope labeling and MALDI-TOF mass spectrometry (MS). In this study, we synthesized benzoic acid-d0 N-succinimidyl ester (BzOSu) and benzoic acid-d5 N-s
- Kurogochi, Masaki,Amano, Junko
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p. 9944 - 9961
(2014/08/05)
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- Bright, highly water-soluble triazacyclononane europium complexes to detect ligand binding with time-resolved FRET microscopy
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Luminescent europium complexes are used in a broad range of applications as a result of their particular emissive properties. The synthesis and application of bright, highly water-soluble, and negatively charged sulfonic- or carboxylic acid derivatives of
- Delbianco, Martina,Sadovnikova, Victoria,Bourrier, Emmanuel,Mathis, Gérard,Lamarque, Laurent,Zwier, Jurriaan M.,Parker, David
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supporting information
p. 10718 - 10722
(2015/05/13)
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- Extremely fast gas/liquid reactions in flow microreactors: Carboxylation of short-lived organolithiums
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Carboxylation of short-lived organolithiums bearing electrophilic functional groups such as nitro, cyano, and alkoxycarbonyl groups with CO 2 to give carboxylic acids and active esters was accomplished in a flow microreactor system. The successful reactions indicate that gas/liquid mass transfer and the subsequent chemical reaction with CO2 are extremely fast. Carboxylation of short-lived organolithiums bearing electrophilic functional groups such as nitro, cyano, and alkoxycarbonyl groups with CO 2 to give carboxylic acids and active esters was accomplished in a flow microreactor system. The successful reactions indicate that gas/liquid mass transfer and the subsequent chemical reaction with CO2 are extremely fast (see scheme).
- Nagaki, Aiichiro,Takahashi, Yusuke,Yoshida, Jun-Ichi
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p. 7931 - 7934
(2014/07/07)
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- A copper-catalysed amidation of aldehydes via N-hydroxysuccinimide ester formation
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A copper-catalysed oxidative amidation of aldehydes via N-hydroxysuccinimide ester formation is reported. The methodology employed to prepare amides directly from aldehydes has a very wide scope, is high yielding, and does not need dry conditions. This cross-coupling reaction appears to be simple and makes use of cheap, abundant and easily available reagents.
- Pilo, Monica,Porcheddu, Andrea,De Luca, Lidia
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p. 8241 - 8246
(2013/12/04)
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- Iodide-catalyzed amide synthesis from alcohols and amines
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An efficient method to prepare amides by a cascade strategy was developed. Using nBu4NI or NaI as the catalyst and tert-butyl hydroperoxide as the oxidant, various alcohols reacted with N-hydroxysuccinimide or N-hydroxyphthalimide affording corresponding active esters in moderate to good yield. The resulting active esters were converted into amides smoothly in one pot. The Royal Society of Chemistry 2013.
- Wang, Gao,Yu, Qing-Ying,Wang, Jian,Wang, Shan,Chen, Shan-Yong,Yu, Xiao-Qi
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p. 21306 - 21310
(2013/11/06)
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- Photocatalytic conversion of CO2 to CO using rhenium bipyridine platforms containing ancillary phenyl or BODIPY moieties
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Harnessing of solar energy to drive the reduction of carbon dioxide to fuels requires the development of efficient catalysts that absorb sunlight. In this work, we detail the synthesis, electrochemistry, and photophysical properties of a set of homologous fac-ReI(CO)3 complexes containing either an ancillary phenyl (8) or BODIPY (12) substituent. These studies demonstrate that both the electronic properties of the rhenium center and BODIPY chromophore are maintained for these complexes. Photolysis studies demonstrate that both assemblies 8 and 12 are competent catalysts for the photochemical reduction of CO2 to CO in dimethylformamide (DMF) using triethanolamine (TEOA) as a sacrificial reductant. Both compounds 8 and 12 display turnover frequencies (TOFs) for photocatalytic CO production upon irradiation with light (λex ≥ 400 nm) of ~5 h -1 with turnover number (TON) values of approximately 20. Although structural and photophysical measurements demonstrate that electronic coupling between the BODIPY and fac-ReI(CO)3 units is limited for complex 12, this work clearly shows that the photoactive BODIPY moiety is tolerated during catalysis and does not interfere with the observed photochemistry. When taken together, these results provide a clear roadmap for the development of advanced rhenium bipyridine complexes bearing ancillary BODIPY groups for the efficient photocatalytic reduction of CO2 using visible light.
- Andrade, Gabriel A.,Pistner, Allen J.,Yap, Glenn P. A.,Lutterman, Daniel A.,Rosenthal, Joel
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p. 1685 - 1692
(2013/09/02)
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- Novel fluorescent risedronates: Synthesis, photodynamic inactivation and imaging of Bacillus subtilis
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Novel fluorescently-labeled conjugates of risedronate were synthesized using an epoxide linker, enabling conjugation of risedronate via its pyridyl nitrogen with the aromatic succinimidyl esters. The compounds were characterized by using 1H NMR, 13C NMR, 31P NMR, UV-vis and fluorescence emission spectroscopies. Biological activity assays showed that the conjugates 14 and 15 exhibited photodynamic inactivation of Bacillus subtilis (ATCC 6633) with 91% and 47% bacterial lethality at 10 μM upon visible light irradiation, respectively. Both 14 and 15 could be also used for fluorescence imaging of Bacillus subtilis.
- Zhou, Li-Sheng,Yang, Ke-Wu,Feng, Lei,Xiao, Jian-Min,Liu, Cheng-Cheng,Zhang, Yi-Lin,Crowder, Michael W.
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supporting information
p. 949 - 954
(2013/03/14)
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- Sialyltransferase inhibitors: Consideration of molecular shape and charge/hydrophobic interactions
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In order to evaluate the importance of molecular shape of inhibitor molecules and the charge/H-bond and hydrophobic interactions, we synthesized three types of molecules and tested them against a sialyltransferase. The first type of compounds were designe
- Kumar, Rishi,Nasi, Ravindranath,Bhasin, Milan,Khieu, Nam Huan,Hsieh, Margaret,Gilbert, Michel,Jarrell, Harold,Zou, Wei,Jennings, Harold J.
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- Organocatalytic amidation and esterification of aldehydes with activating reagents by a cross-coupling strategy
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Formation on demand: An organocatalytic cross-coupling reaction of aldehydes with N-hydroxyimides, hexafluoroisopropyl alcohol, and sulfonimides has been developed. The resulting active intermediates can be directly converted into amides or esters in one pot. This simple method makes use of readily available starting materials, and the newly discovered activating reagents should find broad application in the synthesis of amides and esters. Copyright
- Tan, Bin,Toda, Narihiro,Barbas III, Carlos F.
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supporting information
p. 12538 - 12541
(2013/02/22)
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- Metal-free oxidative amide formation with N-hydroxysuccinimide and hypervalent iodine reagents
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An oxidative amide formation using N-hydroxysuccinimide and hypervalent iodine reagents was developed. The method enables a wide range of aldehydes and amines to be coupled under mild reaction conditions providing amide in good to excellent yield. The radical species in the reaction mixture was observed for the first time using ESR measurement, and along with other mechanistic investigations, a plausible mechanism of the reaction was proposed.
- Yao, Haoyi,Tang, Yun,Yamamoto, Kana
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scheme or table
p. 5094 - 5098
(2012/10/08)
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- SYNTHESIS OF ACYL-PANTETHEINE DERIVATIVES AND THE USE THEREOF IN THE SYNTHESIS OF ACYL-COENZYME A DERIVATIVES
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The present invention relates to a novel synthesis method for acyl-pantetheine derivatives. The present invention further relates to the use of said synthesized acyl-pantetheine derivatives as a starting material in the enzymatic synthesis of acyl-coenzyme A derivatives. According to a first aspect thereof, the present invention provides a method for the synthesis of acyl-pantetheine derivatives, the method including the steps of: a) providing a source of pantetheine; b) providing a source of acyl ester; and c) contacting the source of pantetheine with the source of acyl ester to form the corresponding acyl-pantetheine derivative, having the general formula (I), wherein R is an acyl group.The present invention also provides a method for the synthesis of acyl-coenzyme A derivatives as well as the use of a source of pantetheine and a source of acyl ester in the preparation steps of these two methods.
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Page/Page column 18
(2012/02/15)
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- Aerobic amide bond formation with N-hydroxysuccinimide
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Breathe easy: Molecular oxygen is one of the most abundant, atom-efficient, and economical oxidants. An aerobic oxidative amide formation from aldehydes and amines is reported. The method uses a catalytic amount of Co(OAc) 2 and N-hydroxysuccinimide as reaction promoters. It is applicable to chiral substrates without loss of their optical purity. Copyright
- Yao, Haoyi,Yamamoto, Kana
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supporting information; experimental part
p. 1542 - 1545
(2012/09/08)
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- Synthesis of d-labeled and unlabeled benzoyloxysuccinimides and application to quantitative analysis of peptides and a protein by isotope differential mass spectrometry
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Benzoyloxysuccinimide and its d5-labeled version, which react with amino groups in the N-termini and lysine side chains in proteins, were synthesized and applied to quantitative analysis of peptides and a commercially available protein in combi
- Zabet-Moghaddam, Masoud,Shaikh, Aarif L.,Jones, Lauren B.,Niwayama, Satomi
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experimental part
p. 4629 - 4632
(2011/09/15)
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- Antibacterial Agents
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The invention provides compounds of formula (I) and salts thereof: R1-L-R2—B wherein R1, L, R2, and B have any of the values defined herein, as well as compositions comprising such compounds, and therapeutic methods comprising the administration of such compounds or salts. The compounds block siderophore production in bacteria and are useful as antibacterial agents.
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Page/Page column 35
(2009/01/20)
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- A new generation of specific Trypanosoma cruzi trans-sialidase inhibitors
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(Chemical Equation Presented) A substitution for inhibition: The incorporation of anaryl substituent at C9 of 3-fluorosialyl fluorides provides specificity and dramatically slows the reactivation of the glycosylphosphatidylinositol-anchored surface protein Trypanosoma cruzi trans-sialidase (TcTS) by transglycosylation (see picture). X-ray crystallographic analysis of the trapped intermediate has provided a structural rationale for this behavior.
- Buchini, Sabrina,Buschiazzo, Alejandro,Withers, Stephen G.
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p. 2700 - 2703
(2008/12/23)
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- A conventional new procedure for N-acylation of unprotected amino acids
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The preparation of amide derivatives (4) by N-acylation of unprotected α-amino acids is easily achieved via readily available benzotriazolyl carboxylates (2a-d) or succinimidyl carboxylates (2e-f). These intermediates (2) are prepared from reaction of carboxylic acids (1) with 1-hydroxybenzotriazole (HO-Bt) or N-hydroxysuccinimide (HO-Su) in the presence of equimolar amounts of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (WSCI). The overall yields of the target compounds (4) were excellent, and this two-stage procedure could be applicable as an alternative procedure for one-pot reaction.
- Fujisaki, Fumiko,Oishi, Marumi,Sumoto, Kunihiro
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p. 124 - 127
(2007/10/03)
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- Structure-based design and synthesis of the first weak non-phosphate inhibitors for IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis
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In this paper, we describe the structure-based design, synthesis, and biological evaluation of cytosine derivatives and analogues that inhibit IspF, an enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. This pathway is responsible for the biosynthesis of the C5 precursors to isoprenoids, isopentenyl diphosphate (IPP, 1) and dimethylallyl diphosphate (DMAPP, 2; Scheme 1). The non-mevalonate pathway is the sole source for 1 and 2 in the protozoan Plasmodium parasites. Since mammals exclusively utilize the alternative mevalonate pathway, the enzymes of the non-mevalonate pathway have been identified as attractive new drug targets in the fight against malaria. Based on computer modeling (cf. Figs. 2 and 3), new cytosine derivatives and analogues (Fig. 1) were selected as potential drug-like inhibitors of IspF protein, and synthesized (Schemes 2-5). Determination of the enzyme activity by 13C-NMR spectroscopy in the presence of the new ligands showed inhibitory activities for some of the prepared cytosine and pyridine-2,5-diamine derivatives in the upper micromolar range (IC50 values; Table). The data suggest that it is possible to inhibit IspF protein without binding to the polar diphosphate binding site and the side chain of Asp56′, which interacts with the ribose moiety of the substrate and substrate analogues. Furthermore, a new spacious sub-pocket was discovered which accommodates aromatic spacers between cytosine derivatives or analogues (binding to 'Pocket III') and rings that occupy the flexible hydrophobic region of 'Pocket II'. The proposed binding mode remains to be further validated by X-ray crystallography.
- Baumgartner, Corinne,Eberle, Christian,Diederich, Francois,Lauw, Susan,Rohdich, Felix,Eisenreich, Wolfgang,Bacher, Adelbert
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p. 1043 - 1068
(2008/03/13)
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- BIOLOGICAL MATERIALS AND USES THEREOF
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The invention provides a compound comprising a photosensitising agent coupled to a carrier molecule with a minimum coupling ratio of 3 :1 wherein the carrier molecule has a binding specificity for a target cell. There is also provided a process of conjuga
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Page/Page column 45-46
(2008/06/13)
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- NON-SIGNAL IMIDAZOLE REAGENTS FOR MASS SPECTROMETRY ANALYSIS OF PHOSPHOMONOESTERS
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Analytical chemical reagents termed non- signal imidazoles and a method for their use that provide a host of advantages for analysis of phosphomonoesters are described. The method and compounds of the invention provide a host of advantages for the analysi
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Page/Page column 12-13
(2008/06/13)
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- N-hydroxysuccinimide-promoted oxidation of primary alcohols and aldehydes to form active esters with hypervalent(III) iodine
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A simple, mild, and efficient method for the conversion of primary alcohols and aldehydes to N-hydroxysuccinimide esters with (diacetoxyiodo)benzene in high yield is developed. N-Hydroxysuccinimide acts not only as an esterification partner but also as an activator of PhI(OAc)2 in this reaction. Copyright
- Wang, Naiwei,Liu, Renhua,Xu, Qing,Liang, Xinmiao
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p. 566 - 567
(2007/10/03)
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- Rationally-designed nucleoside antibiotics that inhibit siderophore biosynthesis of Mycobacterium tuberculosis
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A rationally designed nucleoside inhibitor of Mycobacterium tuberculosis growth (MIC99 = 0.19 μM) that disrupts siderophore biosynthesis was identified. The activity is due to inhibition of the adenylate-forming enzyme MbtA which is involved in
- Somu, Ravindranadh V.,Boshoff, Helena,Qiao, Chunhua,Bennett, Eric M.,Barry III, Clifton E.,Aldrich, Courtney C.
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- PROCESS FOR CONVERSION OF PHENOLS TO CARBOXAMIDES VIA THE SUCCINIMIDE ESTERS
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A process for converting an aryl triflate, heteroaryl triflate, aryl halide or heteroaryl halide to an N-hydroxysuccinimido este is disclosed. The process involves reacting the triflate or halide with carbon monoxide and N-hydroxysuccinimide in a solvent in the presence of a palladium catalyst and a base.
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- IBX-mediated oxidation of primary alcohols and aldehydes to form carboxylic acids
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Under mild conditions and without the use of toxic metals, the oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids with 1-hydroxy-1,2-benziodoxole-3(1H)-one-1-oxide (IBX) proceeds in the presence of 1-hydroxypyridine or N-hydroxysuccinimide (see scheme). The reaction tolerates a wide variety of functional groups.
- Mazitschek, Ralph,Muelbaier, Marcel,Giannis, Athanassios
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p. 4059 - 4061
(2007/10/03)
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- O-succinimidyl-1,3-dimethyl-1,3-trimethyleneuronium salts as efficient reagents in active ester synthesis
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The new uronium salts O-succinimidyl-1,3-dimethyl-1,3-trimethyleneuronium hexafluorophosphate (HSDU) and tetrafluoroborate (TSDU) have been prepared from 1,3-dimethylpropyleneurea (DMPU) and employed in the synthesis of N-hydroxysuccinimide-derived active esters. High yields were obtained at room temperature in short reaction times and no racemization was observed.
- Bailén, Miguel A,Chinchilla, Rafael,Dodsworth, David J,Nájera, Carmen
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p. 1661 - 1664
(2007/10/03)
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