- Discovery and Structure-Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δModulators
-
Following our report that A3 adenosine receptor (AR) antagonist 1 exhibited a polypharmacological profile as a dual modulator of peroxisome proliferator-activated receptor (PPAR)γ/δ, we discovered a new template, 1′-homologated adenosine analogues 4a-4t, as dual PPARγ/δmodulators without AR binding. Removal of binding affinity to A3AR was achieved by 1′-homologation, and PPARγ/δdual modulation was derived from the structural similarity between the target nucleosides and PPAR modulator drug, rosiglitazone. All the final nucleosides were devoid of AR-binding affinity and exhibited high binding affinities to PPARγ/δbut lacked PPARα binding. 2-Cl derivatives exhibited dual receptor-binding affinity to PPARγ/δ, which was absent for the corresponding 2-H derivatives. 2-Propynyl substitution prevented PPARδ-binding affinity but preserved PPARγaffinity, indicating that the C2 position defines a pharmacophore for selective PPARγligand designs. PPARγ/δdual modulators functioning as both PPARγpartial agonists and PPARδantagonists promoted adiponectin production, suggesting their therapeutic potential against hypoadiponectinemia-associated cancer and metabolic diseases.
- An, Seungchan,Kim, Gyudong,Kim, Hyun Jin,Ahn, Sungjin,Kim, Hyun Young,Ko, Hyejin,Hyun, Young Eum,Nguyen, Mai,Jeong, Juri,Liu, Zijing,Han, Jinhe,Choi, Hongseok,Yu, Jinha,Kim, Ji Won,Lee, Hyuk Woo,Jacobson, Kenneth A.,Cho, Won Jea,Kim, Young-Mi,Kang, Keon Wook,Noh, Minsoo,Jeong, Lak Shin
-
p. 16012 - 16027
(2021/01/09)
-
- Total Synthesis of 6-Amino-2,6-dideoxy-α-Kdo from d -Mannose
-
3-Deoxy-d-manno-oct-2-ulosonic acid (Kdo) biosynthetic pathway is a promising target in antibacterial drug discovery. Herein, we report the total synthesis of 6-amino-2,6-dideoxy-α-Kdo in 15 steps from d-mannose as a potential inhibitor of Kdo-processing
- Ameur, Nassima,Gamboa Marin, Oscar Javier,Gauthier, Charles,Gormand, Paul,Hussain, Nazar,Ravicoularamin, Gokulakrishnan,Sauvageau, Janelle
-
supporting information
(2020/07/27)
-
- Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues
-
Queuosine (Q) is a hypermodified RNA nucleoside that is found in tRNAHis, tRNAAsn, tRNATyr, and tRNAAsp. It is located at the wobble position of the tRNA anticodon loop, where it can interact with U as well as C bases located at the respective position of the corresponding mRNA codons. In tRNATyr and tRNAAsp of higher eukaryotes, including humans, the Q base is for yet unknown reasons further modified by the addition of a galactose and a mannose sugar, respectively. The reason for this additional modification, and how the sugar modification is orchestrated with Q formation and insertion, is unknown. Here, we report a total synthesis of the hypermodified nucleoside galactosyl-queuosine (galQ). The availability of the compound enabled us to study the absolute levels of the Q-family nucleosides in six different organs of newborn and adult mice, and also in human cytosolic tRNA. Our synthesis now paves the way to a more detailed analysis of the biological function of the Q-nucleoside family.
- Carell, Thomas,Ensfelder, Timm T.,Heiss, Matthias,Hillmeier, Markus,Kellner, Stefanie,Müller, Markus,Michalakis, Stylianos,Sch?n, Alexander,Scheel, Constanze,Thumbs, Peter,Wagner, Mirko
-
supporting information
p. 12352 - 12356
(2020/04/27)
-
- Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals
-
A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehy
- Choutka, Jan,Kratochvíl, Michal,Parkan, Kamil,Pohl, Radek,Zyka, Jakub
-
supporting information
(2020/08/24)
-
- PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING GLAUCOMA, CONTAINING ADENOSINE DERIVATIVE
-
A pharmaceutical composition for preventing or treating eye diseases and an oral administration agent for preventing or treating eye diseases are provided. The pharmaceutical composition for preventing or treating eye diseases comprises the compound repre
- -
-
Paragraph 0126-0130
(2020/02/05)
-
- Compound, preparation method and applications thereof, and glycosidase inhibitor
-
The invention relates to the field of enzyme inhibitors, and discloses a compound, a preparation method and applications thereof, and a glycosidase inhibitor, wherein the compound has a structure represented by a formula (I), R is any one selected from hy
- -
-
Paragraph 0068-0071
(2019/10/01)
-
- PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING NONALCOHOLIC STEATOHEPATITIS, HEPATIC FIBROSIS, AND LIVER CIRRHOSIS, COMPRISING ADENOSINE DERIVATIVES
-
A pharmaceutical composition for preventing or treating liver disease is provided. The pharmaceutical composition comprising a compound represented by formula 1 below or a pharmaceutically acceptable salt of the compound as an active ingredient: where A i
- -
-
Paragraph 0082
(2019/09/15)
-
- Synthesis of Butenolides via a Horner-Wadsworth-Emmons Cascading Dimerization Reaction
-
The efficient synthesis of a range of structurally related butenolides has been observed while we were exploring the substrate-scope of a Horner-Wadsworth-Emmons (HWE) reaction. While aliphatic aldehydes gave the expected HWE product, aromatic aldehydes f
- Everson, Jack,Kiefel, Milton J.
-
p. 15226 - 15235
(2019/11/21)
-
- Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity
-
[Figure not available: see fulltext.] Copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4·5H2O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil–mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 μM, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.
- Halay, Erkan,Ay, Emriye,?alva, Emine,Ay, Kadir,Karay?ld?r?m, Tamer
-
p. 158 - 166
(2018/04/02)
-
- Undemanding Synthesis of Novel C19 and C17 Analogues of C18-Guggultetrol
-
A simple and undemanding synthesis of (2S,3R,4R,5R)-nonadecane-1,2,3,4,5-pentol and (2S,3R)-heptadecane-1,2,3-triol as novel C19 and C17 analogues of C18-guggultetrol was achieved by using l-ascorbic acid as a chiral pool.
- Dhage, Ganesh R.,Thopate, Shankar R.
-
supporting information
p. 970 - 972
(2017/05/05)
-
- Practical preparation of mono- and di-O-isopropylidene derivatives of monosaccharides and methyl 4,6-O-benzylidene glycosides from free sugars in a deep eutectic solvent
-
Free sugars were rapidly converted into the corresponding di-O-isopropylidene derivatives and methyl O-benzylidene glycosides in excellent yields and purity in a deep eutectic solvent made from choline chloride and malonic acid (ChCl:MA). Reaction conditions were mild; work-up was easy, and further purification was not necessary. Given the inexpensive, nontoxic, and recyclable nature of ChCl:MA, this protocol is environmental friendly.
- Rokade, Sunil M.,Bhate, Prakash M.
-
-
- A sulfur-containing thick mixed four ring aza sugar derivative and its preparation method
-
The invention discloses a sulfur-containing thick and mixed tetracyclic azasugar derivative, which has a general chemical formula as shown in figure I. A preparation method of the sulfur-containing thick and mixed tetracyclic azasugar derivative comprises
- -
-
Paragraph 0038; 0041; 0042
(2017/08/15)
-
- Synthesis of Iminosugar-Containing KRN7000 Analogues
-
Three new iminosugar-containing KRN7000 (also referred to as α-GalCer) analogues were designed and synthesized. In the design, the galactose moiety of KRN7000 was replaced by iminosugars and the iminosugar structures were connected with ceramide in differ
- Zhang, Lei,Ye, Xin-Shan
-
p. 1001 - 1008
(2017/06/27)
-
- Click Inspired Synthesis of 1,2,3-Triazole-linked 1,3,4-Oxadiazole Glycoconjugates
-
The glycoconjugation of biologically privileged 1,3,4-oxadiazole scaffold is described via Cu(I)-catalyzed azide–alkyne cycloaddition. A series of glycosyl alkynes 1b–i, obtained from various commercial sugars, were treated with azide functionalized 1,3,4-oxadiazole using click chemistry to access triazole-linked glycosylated 1,3,4-oxadiazoles 10b–i in good yields. The structure of the developed glycoconjugates has been ascertained by extensive spectroscopic analysis (1H &13C NMR, IR, and MS).
- Kushwaha, Divya,Tiwari, Vinod K.
-
p. 2454 - 2462
(2017/07/25)
-
- Synthesis of oxylipin mimics and their antifungal activity against the citrus postharvest pathogens
-
Nine oxylipin mimics were designed and synthesized starting from D-mannose. Their antifungal activity against three citrus postharvest pathogens was evaluated by spore germination assay. The results indicated that all the compounds significantly inhibited the growth of Penicillium digitatum, Penicillium italicum and Aspergillus Niger. The compound (3Z,6Z,8S,9R,10R)-octadeca-3,6-diene-8,9,10-triol (3) exhibited excellent inhibitory effect on both Penicillium digitatum (IC50 = 34 ppm) and Penicillium italicum (IC50 = 94 ppm). Their in vivo antifungal activities against citrus postharvest blue mold were tested with fruit inoculated with the pathogen Penicillium italicum. The compound (3R,4S)-methyl 3,4-dihydroxy-5-octyltetrahydrofuran-2-carboxylate (9) demonstrated significant efficacy by reducing the disease severity to 60%. The antifungal mechanism of these oxylipin mimics was postulated in which both inhibition of pathogenic mycelium and stimuli of the host oxylipin-mediated defense response played important roles.
- Ma, Jimei,Li, Yupeng,Chen, Hangwei,Zeng, Zhen,Li, Zi-Long,Jiang, Hong
-
-
- Efficient Large Scale Syntheses of 3-Deoxy- d -manno-2-octulosonic acid (Kdo) and Its Derivatives
-
An efficient method to rapidly synthesize 3-deoxy-d-manno-2-octulosonic acid (Kdo) and its derivatives in large scale has been developed. Starting from d-mannose, the di-O-isopropylidene derivative of Kdo ethyl ester was prepared in three steps on a scale of more than 40 g in one batch in an overall yield of 75-80% without any intermediate purification. Kdo, Kdo glycal, and 2-acetylated Kdo ester were synthesized quickly in high yield from a di-O-isopropylidene derivative of Kdo ethyl ester. 2-Deoxy-β-Kdo ester was obtained with high stereoselectivity via the epimerization of the α-isomer using t-BuOH as a proton source.
- Feng, Yingle,Dong, Jie,Xu, Fangyuan,Liu, Aiyun,Wang, Li,Zhang, Qi,Chai, Yonghai
-
supporting information
p. 2388 - 2391
(2015/05/27)
-
- Lead tetraacetate mediated one pot oxidative cleavage and acetylation reaction: an approach to apio and homologated apio pyrimidine nucleosides and their anticancer activity
-
An efficient and versatile strategy of general applicability towards apio and homologated apio pyrimidines has been delineated. The methodology shows tosylation followed by in situ cyclization and one pot oxidative cleavage and acetylation by Pb(OAc)4 as the key steps. The methodology has been applied to d-ribose and d-mannose derivatives to achieve asymmetric synthesis of apio and homologated apio pyrimidine nucleosides.
- Panda, Amarendra,Islam, Sehbanul,Santra, Manas Kumar,Pal, Shantanu
-
p. 82450 - 82459
(2015/10/12)
-
- A highly efficient catalyst for selective oxidative scission of olefins to aldehydes: Abnormal-NHC-Ru(II) complex in oxidation chemistry
-
The utility and selectivity of the catalyst [Ru(COD)(L1)Br2] (1) bearing a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based abnormal N-heterocyclic carbene ligand L1 is demonstrated toward selective oxidation of C=C bonds to aldehydes and C=C bonds to α-diketones in an EtOAc/CH3CN/H2O solvent mixture at room temperature using a wide range of substrates, including highly functionalized sugar- and amino acid-derived compounds.
- Daw, Prosenjit,Petakamsetty, Ramu,Sarbajna, Abir,Laha, Siladitya,Ramapanicker, Ramesh,Bera, Jitendra K.
-
supporting information
p. 13987 - 13990
(2015/01/08)
-
- CARBOHYDRATE PHOSPHONATE DERIVATIVES AS MODULATORS OF GLYCOSYLATION
-
Compounds of Formula (I) are useful as modulators of glycosylation. Compounds of Formula (I) have the following structure: (I) and the definitions of the other variables are provided herein.
- -
-
Paragraph 0108
(2014/09/03)
-
- GLYCOSIDASE INHIBITORS AND USES THEREOF
-
The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.
- -
-
Paragraph 00170
(2014/03/25)
-
- A chiron approach to aminocytitols by petasis-borono-mannich reaction: Formal synthesis of (+)-conduramine e and (-)-conduramine e
-
A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-β-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.
- Ghosal, Partha,Shaw, Arun K.
-
supporting information
p. 7627 - 7632,6
(2020/08/24)
-
- Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines
-
A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio-and diastereoselective Strecker reaction.
- Matassini, Camilla,Mirabella, Stefania,Goti, Andrea,Cardona, Francesca
-
supporting information; experimental part
p. 3920 - 3924
(2012/09/08)
-
- Synthesis of N-homobicyclic dideoxynucleoside analogues
-
Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by f
- Raghavendra Swamy,Suryakiran,Paradesi Naidu,Venkateswarlu
-
experimental part
p. 191 - 196
(2012/06/30)
-
- Organoiridium complexes: Efficient catalysts for the formation of sugar acetals and ketals
-
[Cp*IrCl2]2 is used as an efficient promoter for the synthesis of sugar acetals and ketals with good to excellent yields. The catalyst is found to be general for a wide range of sugars.
- Mandal, Soumik,Verma, Prashant Ranjan,Mukhopadhyay, Balaram,Gupta, Parna
-
experimental part
p. 2007 - 2010
(2011/12/01)
-
- Highly efficient synthesis of ketoheptoses
-
A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.
- Waschke, Daniel,Thimm, Julian,Thiem, Joachim
-
supporting information; experimental part
p. 3628 - 3631
(2011/09/15)
-
- Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives
-
Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives were prepared and fully characterized. The procedure is generally applicable to monosaccharides and thus facilitates access to differently substituted glycosidic precursors.
- Kunig, Johannes,L?nnecke, Peter,Hey-Hawkins, Evamarie
-
scheme or table
p. 1154 - 1160
(2011/06/21)
-
- Total syntheses of tubulysins
-
The total syntheses of tetrapeptides tubulysins D (1b), U (1c), and V (1d), which are potent tubulin polymerization inhibitors, are described. The synthesis of Tuv (2), an unusual amino acid constituent of tubulysins, includes an 1,3-dipolar cycloaddition
- Shibue, Taku,Hirai, Toshihiro,Okamoto, Iwao,Morita, Nobuyoshi,Masu, Hyuma,Azumaya, Isao,Tamura, Osamu
-
supporting information; experimental part
p. 11678 - 11688
(2010/11/18)
-
- Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents
-
Furanosyl and pyranosyl chlorides react with aryllithium derivatives, obtained by directed ortho-lithiation of activated arenes, to give C-1 aryl glycals in moderate yields.
- Goemez, Ana M.,Casillas, Marta,Rodriguez, Benjamin,Valverde, Serafin,Loepez, J. Cristoebal
-
scheme or table
p. 288 - 302
(2010/08/07)
-
- A simple and convenient synthetic protocol for O-isopropylidenation of sugars using bromodimethylsulfonium bromide (BDMS) as a catalyst
-
Various O-isopropylidene derivatives of sugars and acyclic sugars were obtained in very good yields on reaction with acetone at room temperature with a catalytic amount of bromodimethylsulfonium bromide (BDMS). These O-isopropylidene derivatives can also be prepared in good yields on reaction with 2,2-dimethoxypropane (DMP) in acetonitrile using the same catalyst in shorter reaction times. Some of the advantages of this method are high effectiveness, a nonaqueous workup procedure, economic viability, and good yields.
- Khan, Abu T.,Musawwer Khan
-
experimental part
p. 154 - 159
(2011/03/19)
-
- Design, synthesis, and binding of homologated truncated 4′-thioadenosine derivatives at the human A3 adenosine receptors
-
We synthesized homologated truncated 4′-thioadenosine analogues 3 in which a methylene (CH2) group was inserted in place of the glycosidic bond of a potent and selective A3 adenosine receptor antagonist 2. The analogues were designed
- Lee, Hyuk Woo,Kim, Hea Ok,Choi, Won Jun,Choi, Sun,Lee, Jin Hee,Park, Seul-Gi,Yoo, Lena,Jacobson, Kenneth A.,Jeong, Lak Shin
-
scheme or table
p. 7015 - 7021
(2010/10/21)
-
- Development and characterization of lysine based tripeptide analogues as inhibitors of Sir2 activity
-
Sirtuins are NAD+ dependent deacetylases that modulate various essential cellular functions. Development of peptide based inhibitors of Sir2s would prove useful both as pharmaceutical agents and as effectors by which downstream cellular alterations can be monitored. Click chemistry that utilizes Huisgen's 1,3-dipolar cycloaddition permits attachment of novel modifications onto the side chain of lysine. Herein, we report the synthesis of peptide analogues prepared using click reactions on Nε-propargyloxycarbonyl protected lysine residues and their characterization as inhibitors of Plasmodium falciparum Sir2 activity. The peptide based inhibitors exhibited parabolic competitive inhibition with respect to acetylated-peptide substrate and parabolic non-competitive inhibition with NAD+ supporting the formation of EI2 and E·NAD+·I2 complexes. Cross-competition inhibition analysis with the non-competitive inhibitor nicotinamide (NAM) ruled out the possibility of the NAM-binding site being the second inhibitor binding site, suggesting the presence of a unique alternate pocket accommodating the inhibitor. One of these compounds was also found to be a potent inhibitor of the intraerythrocytic growth of P. falciparum with 50% inhibitory concentration in the micromolar range.
- Chakrabarty, Subhra Prakash,Ramapanicker, Ramesh,Mishra, Roli,Chandrasekaran, Srinivasan,Balaram, Hemalatha
-
scheme or table
p. 8060 - 8072
(2010/03/24)
-
- Synthesis of C-1 alkyl and aryl glycals from pyranosyl or furanosyl chlorides by treatment with organolithium reagents
-
Glycosyl chlorides, with ether or isopropylidene acetal protecting groups, readily available from furanoses or pyranoses, can be conveniently transformed into C-1 alkyl or aryl glycals by reaction with alkyl or aryl organolithium reagents.
- Gomez, Ana M.,Pedregosa, Ana,CasiIIas, Marta,Uriel, Clara,Lopez, J. Cristobal
-
experimental part
p. 3579 - 3588
(2009/10/26)
-
- Stereoselective synthesis of L-guluronic acid alginates
-
The glycosylation properties of gulopyranosides have been mapped out, and it is shown that gulose has an intrinsic preference for the formation of 1,2-cis-glycosidic bonds. It is postulated that this glycosylation behaviour originates from nucleophilic attack at the oxacarbenium ion, which adopts the most favourable 3H4 conformation. Building on the stereoselectivity of gulose, a guluronic acid alginate trisaccharide was assembled for the first time by using gulopyranosyl building blocks.
- Dinkelaar, Jasper,Van Den Bos, Leendert J.,Hogendorf, Wouter F. J.,Lodder, Gerrit,Overkleeft, Herman S.,Codee, Jeroen D. C.,Van Der Marel, Gijsbert A.
-
experimental part
p. 9400 - 9411
(2009/09/06)
-
- Indium(III) triflate: A highly efficient catalyst for reactions of sugars
-
Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3 led to the formation of the corresponding thioglycoside in high yield. Facile formation and hydrolysis of the isopropylidene and benzylidene acetals of various carbohydrates have also been achieved very efficiently in the presence of In(OTf)3. The results show great promise for In(OTf)3 in synthetic carbohydrate chemistry.
- Giri, Santosh Kumar,Verma, Monika,Kartha, K. P. Ravindranathan
-
scheme or table
p. 464 - 478
(2009/04/06)
-
- ADENOSINE DERIVATIVES, METHOD FOR THE SYNTHESIS THEREOF, AND THE PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF THE INFLAMMATORY DISEASES CONTAINING THE SAME AS AN ACTIVE INGREDIENT
-
Disclosed are adenosine derivatives, methods for the synthesis thereof, and pharmaceutical compositions for the prevention and treatment of inflammatory diseases, comprising the same as an active ingredient. The adenosine derivatives have high binding aff
- -
-
Page/Page column 28-29
(2008/12/08)
-
- First synthesis of 4′-selenonucleosides showing unusual southern conformation
-
(Chemical Equation Presented) The first synthesis of 4′- selenonucleosides was achieved using a Pummerer-type condensation as a key step. All stereoelectronic effects shown in 4′-oxonucleosides were overwhelmed by the size of selenium and steric interacti
- Lak, Shin Jeong,Tosh, Dilip K.,Hea, Ok Kim,Wang, Ting,Hou, Xiyan,Ho, Seop Yun,Kwon, Youngjoo,Sang, Kook Lee,Choi, Jungwon,Long, Xuan Zhao
-
p. 209 - 212
(2008/09/19)
-
- Disaccharides as sialic acid aldolase substrates: Synthesis of disaccharides containing a sialic acid at the reducing end
-
(Chemical Equation Presented) Synthesis with an unfussy enzyme: Escherichia coli sialic acid aldolase has been found to be unusually flexible in accepting disaccharides containing a mannose (Man) or N-glycolylmannosamine (ManNGc) at the reducing end as su
- Huang, Shengshu,Yu, Hai,Chen, Xi
-
p. 2249 - 2253
(2008/03/13)
-
- O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate
-
Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash.
- Lin, Chun-Cheng,Jan, Mi-Dan,Weng, Shiue-Shien,Lin, Chang-Ching,Chen, Chien-Tien
-
p. 1948 - 1953
(2007/10/03)
-
- One-pot carbanionic synthesis of P1,P2-diglycosyl, P1,P1,P2-triglycosyl, and P1,P 1,P2,P2-tetraribosyl methylenediphosphonates
-
Novel lithiated carbanions derived from ethyl glycosyl- and diglycosyl methylphosphonates were used in a direct and convenient synthesis of P 1,P2-diglycosyl, P1,P1,P 2-triglycosyl and P1,P
- Grison, Claude,Chibli, Hicham,Barthes, Nicolas,Coutrot, Philippe
-
p. 7978 - 7988
(2007/10/03)
-
- Catalytic transfer hydrogenation reactions of PEG-bound succinyl esters
-
Various substrates bound to polyethylene glycol (PEG) through succinyl ester linkages were cleaved under catalytic transfer hydrogenation conditions. The substrates with unsaturated functions also underwent hydrogenation. The protocol was found to be suit
- Kumar, H. M. Sampath,Chakravarthy, Pawan,Sawant, Sanghapal D.,Singh, Parvinder Pal,Shesha Rao,Yadav
-
p. 3591 - 3593
(2007/10/03)
-
- Norrisolide: Total synthesis and related studies
-
A stereoselective synthesis of (+)-norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused γ-lactone-γ-lactol ring system attached to a bicyclic hydrophobic core.
- Brady, Thomas P.,Kim, Sun Hee,Wen, Ke,Kim, Charles,Theodorakis, Emmanuel A.
-
p. 7175 - 7190
(2007/10/03)
-
- NANOPARTICLES FOR DRUG-DELIVERY
-
This invention relates to a unique process for the preparation of polymeric nanoparticles with target molecules bonded to the surface of the particles and having sizes of up to 1000nm, preferably Inm to 400nm, more preferably Inm to 200nm, that are dispersed homogeneously in aqueous solution. To accomplish the above objective, the polymeric nanoparticles of the subject invention are prepared using a novel technique of microemulsion polymerization. The resulting aqueous solution of polymeric nanoparticles is comprised of about 1 to 100 parts per weight of water or buffer, about 1 to 80 parts per weight of polymeric nanoparticles, which the bio-active molecules are conjugated, about 0.001 to 10 parts per weight of emulsifier, and about 0.00001 to 5 parts per weight of radical initiator based on the weight of the solution. In the method of this invention, the target drug/target substance is covalently bonded to the polymeric nanoparticles to secure them from outer intervention in vivo or cell culture in vitro until they are exposed at the target site within the cell.
- -
-
Page/Page column 53; 54
(2008/06/13)
-
- First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides
-
The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by int
- Cristau, Henri-Jean,Monbrun, Jér?me,Schleiss, Julie,Virieux, David,Pirat, Jean-Luc
-
p. 3741 - 3744
(2007/10/03)
-
- Practical synthesis of D-[1-13C]mannose, L-[1-13C] and L-[6-13C]fucose
-
The chemical synthesis of 13C-labeled mannose and fucose is important for the preparation of molecular probes used in the conformational study of the oligosaccharide portions of glycoproteins. A new method for the synthesis of the title [1-sup
- Sato, Ken-Ichi,Akai, Shoji,Youda, Hiroki,Kojima, Masaru,Sakuma, Mayumi,Inaba, Shu-Ichirou,Kurosawa, Kyota
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p. 237 - 243
(2007/10/03)
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- Kiliani on ketoses: Branched carbohydrate building blocks from D-fructose and L-sorbose
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Protected branched sugar lactones are available via Kiliani-acetonation sequences on readily available ketoses such as d-fructose and l-sorbose. In both cases, the readily crystallized diacetonides have a 2,3-cis-diol relationship in the product lactone. An efficient double inversion of the configuration at C-4 and C-5 of the product from d-fructose gives access to the formal Kiliani product from l-psicose. Branched carbohydrate lactones are likely to be of significant value as chirons for homochiral targets with functionalized quaternary centres.
- Hotchkiss, David,Soengas, Raquel,Simone, Michela Iezzi,Van Ameijde, Jeroen,Hunter, Stuart,Cowley, Andrew R.,Fleet, George W.J.
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p. 9461 - 9464
(2007/10/03)
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- Mechanism of 4,6-O-benzylidene-directed β-mannosylation as determined by α-deuterium kinetic isotope effects
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Considerable oxacarbenium ion character may be in the transition state of a highly β-selective mannosylation reaction that proceeds via an α-mannosyl triflate. An α-deuterium kinetic isotope effect of 1.2 was measured at -78 °C (=1.1 at 25 °C). This infor
- Crich, David,Chandrasekera, N. Susantha
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p. 5386 - 5389
(2007/10/03)
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- Hydroxycyclopentanone derivatives from D-mannose via ring closing metathesis: An improved synthesis of a key intermediate of tricyclo-DNA
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A large scale, 10 step synthesis of cyclopentanone 1, starting from the chiral pool compound D-mannose, is described. The synthesis proceeds via a ring closing metathesis reaction as the key step in an overall yield of 23%. Cyclopentanone 1 is a central intermediate for the synthesis of tricyclo-DNA.
- Vonlanthen, David,Leumann, Christian J.
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p. 1087 - 1090
(2007/10/03)
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- Synthesis of 3-deoxy-2-ulosonic acid KDO and 4-epi-KDN, a highly efficient approach of 3-C homologation by propargylation and oxidation
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Through the introduction of a pyruvate segment by asymmetric propargylation and oxidation of terminal alkynes, both KDO and 4-epi-KDN have been concisely synthesized in the furanose form from readily available sugars in high overall yields.
- Li, Lian-Sheng,Wu, Yu-Lin
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p. 9049 - 9054
(2007/10/03)
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- Bicyclic diazasugars. Part 3: β-D-Mannose and 6-deoxy-β-L-gulose analogues
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A bicyclic analogue of β-D-mannopyranose with nitrogen atoms replacing the ring and glycosidic oxygen atoms has been prepared in a single step from 5-O-mesyl-D-mannofuranose by a process that likely involves double displacement and an epoxide intermediate. A similar but protected bicyclic analogue of 6-deoxy-β-L-gulopyranose has been prepared by an electrophilic cyclization reaction.
- Berges, David A,Fan, Jianmei,Liu, Nannan,Kent Dalley
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p. 9915 - 9924
(2007/10/03)
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