- A multifunctional anomeric linker for the chemoenzymatic synthesis of complex oligosaccharides
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A new anomeric linker has been developed that facilitates the purification of glycans prepared by chemoenzymatic approaches and can readily give compounds that are appropriately modified for microarray development or glycan derivatives with a free reducing end that are needed as standards for the development of analytical protocols.
- Prudden, Anthony R.,Chinoy, Zoeisha S.,Wolfert, Margreet A.,Boons, Geert-Jan
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Read Online
- A releasable disulfide carbonate linker for molecular hydrogelations
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We used a releasable disulfide carbonate linker to construct precursors of gelators and form stable gels.
- Liu, Qicai,Ou, Caiwen,Ren, Chunhua,Wang, Ling,Yang, Zhimou,Chen, Minsheng
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Read Online
- Repetitive solid-phase synthesis of polyamines
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A repetitive solid-phase method for the synthesis of polyamines is described. Primary amino groups attached to a crosslinked polystyrene resin are monoalkylated by acid labile, benzhydryl-based alkyl chlorides. Reductive alkylation of the resulting secondary amino group by Fmoc-protected aminoaldehydes gives a N-benzhydryl polyamine backbone. Treatment of the resin with trifluoroacetic acid cleaves both the benzhydryl protective group and the polyamine derivative from the resin. By using benzhydryl protective groups with different acid stability, unbranched, branched and partly branched polyamines are synthesized.
- J?nsson, Daniel,Undén, Anders
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Read Online
- Design and synthesis of a novel peptidomimetic inhibitor of HIV-1 Tat-TAR interactions: Squaryldiamide as a new potential bioisostere of unsubstituted guanidine
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By performing RNA-targeted structure-activity relationship studies, we discovered a novel peptidomimetic containing squaryldiamide as a potential bioisostere replacement for guanidine that binds transactivation responsive RNA with high affinity.
- Lee, Chi-Wan,Cao, Hong,Ichiyama, Kozi,Rana, Tariq M.
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Read Online
- Alcohols immobilization onto 2-chlorotritylchloride resin under microwave irradiation
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The immobilization of alcohols onto 2-chlorotritylchloride resin using microwave irradiation was studied. Three different Fmoc-aminoalcohols were tested: the phenol-like Fmoc-tyramine, the primary alcohol Fmoc-ethanolamine, and the secondary alcohol Fmoc-
- Rizzi, Luca,Cendic, Katarina,Vaiana, Nadia,Romeo, Sergio
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Read Online
- Preparation method of triphosphate compound and deoxynucleotide
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The invention discloses a preparation method of a triphosphate compound and deoxynucleotide. In the preparation method of the triphosphate compound, tetrahydrofuran is used for replacing trimethyl phosphate/triethyl phosphate, tri-n-propylamine is used for replacing tri-n-butylamine, and acetonitrile is used for replacing N,N-dimethylformamide; so that the preparation method has the advantages that the yield is high, few byproducts are produced, a solvent is easy to remove, and the triphosphate compound is non-toxic, safe and the like. According to the preparation method of the deoxynucleotide, the morpholine dimethylformamide solution is used for replacing a triethylamine solution to remove the F-moc group, so that the reaction time is greatly shortened, the generation of byproducts is reduced, and the yield is improved.
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Paragraph 0107-0109
(2020/11/23)
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- Method for stereoselective preparation of beta type single/double artemisinin (symmetric and asymmetric) alkyl ether amine maleate
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The invention relates to the field of organic synthesis and pharmaceutical intermediates, particularly to a method for stereoselective preparation of beta type single/double artemisinin (symmetric andasymmetric) alkyl ether amine maleate. The method compr
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Paragraph 0057; 0066-0069
(2019/01/08)
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- MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS
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Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.
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Paragraph 001283
(2018/09/12)
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- Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from N-Fmoc-Protected α-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library
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A fast and facile synthesis of a series of 4-nitrophenyl 2-azidoethylcarbamate derivatives as activated urea building blocks was developed. The N-Fmoc-protected 2-aminoethyl mesylates derived from various commercially available N-Fmoc-protected α-amino ac
- Chen, Ying-Ying,Chang, Li-Te,Chen, Hung-Wei,Yang, Chia-Ying,Hsin, Ling-Wei
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p. 131 - 136
(2017/04/24)
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- ORGANIC COMPOUNDS TO TREAT HEPATITIS B VIRUS
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The disclosure relates to compositions comprising a HBV RNAi agent. In some embodiments, the HBV RNAi agent comprises a sense and an anti-sense strand, each strand being an 18-mer and the strands together forming a blunt-ended duplex, wherein the 3′ end of at least one strand terminates in a phosphate or modified internucleoside linker and further comprises, in 5′ to 3′ order: a spacer; a second phosphate or modified internucleoside linker; and a 3′ end cap. In some embodiments, the 3′ end of both the sense and anti-sense strand further comprise, in 5′ to 3′ order: a spacer; a second phosphate or modified internucleoside linker; and a 3′ end cap. The two strands can have the same or different spacers, phosphates or modified internucleoside linkers, and/or 3′ end caps. The strands can be ribonucleotides, or, optionally, one or more nucleotide can be modified or substituted. Optionally, at least one nucleotide comprises a modified internucleoside linker. Optionally, the RNAi agent can be modified on one or both 5′ end. Optionally, the sense strand can comprise a 5′ end cap which reduces the amount of the RNA interference mediated by this strand. Optionally, the RNAi agent is attached to a ligand. This format can be used to devise RNAi agents to a variety of different targets and sequences. The disclosure also relates to processes for making such compositions, and methods and uses of such compositions, e.g., to mediate RNA interference. The disclosure also pertains to methods of treating, ameliorating and preventing HBV in a patient involving the step of administering to the patient a therapeutic amount of a HBV RNAi agent.
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Paragraph 0602; 0607
(2016/08/17)
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- Base-Free Iridium-Catalyzed Hydrogenation of Esters and Lactones
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Half-sandwich iridium bipyridine complexes catalyze the hydrogenation of esters and lactones under base-free conditions. The reactions proceed with a variety of ester and lactone substrates. Mechanistic studies implicate a pathway involving rate-limiting hydride transfer to the substrate at high pressures of H2 (≥50 bar).
- Brewster, Timothy P.,Rezayee, Nomaan M.,Culakova, Zuzana,Sanford, Melanie S.,Goldberg, Karen I.
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p. 3113 - 3117
(2016/07/06)
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- A greener, efficient and catalyst-free ultrasonic-assisted protocol for the n-fmoc protection of amines
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A simple, eco-sustainable method for the N-(9-fluorenylmethoxycarbonyl) (N-Fmoc) protection of various structurally amines under ultrasonic irradiation is reported. The corresponding N-Fmoc derivatives were obtained in good to excellent yields within short reaction time. The reaction proceeds without the formation of any side product. Mildness, efficiency and easier work are the main advantages of this new protocol.
- Mansouri, Rachida,Aouf, Zineb,Lakrout, Salah,Berredjem, Malika,Aouf, Nour-Eddine
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p. 546 - 550
(2016/03/19)
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- 3'END CAPS FOR RNAi AGENTS FOR USE IN RNA INTERFERENCE
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The disclosure relates to novel compounds and compositions comprising a RNAi agent comprising a novel compound as a 3' end cap. The disclosure also relates to processes for making such compositions, and methods and uses of such compositions, e.g., to mediate RNA interference.
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Page/Page column 160
(2015/04/22)
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- N-Urethane protection of amines and amino acids in an ionic liquid
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An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.
- Di Gioia,Gagliardi,Leggio,Leotta,Romio,Liguori
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p. 63407 - 63420
(2015/08/11)
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- New charge-bearing amino acid residues that promote β-sheet secondary structure
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Proteinogenic amino acid residues that promote β-sheet secondary structure are hydrophobic (e.g., Ile or Val) or only moderately polar (e.g., Thr). The design of peptides intended to display β-sheet secondary structure in water typically requires one set of residues to ensure conformational stability and an orthogonal set, with charged side chains, to ensure aqueous solubility and discourage self-association. Here we describe new amino acids that manifest substantial β-sheet propensity, by virtue of β-branching, and also bear an ionizable group in the side chain.
- Maynard, Stacy J.,Almeida, Aaron M.,Yoshimi, Yasuharu,Gellman, Samuel H.
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supporting information
p. 16683 - 16688
(2015/02/05)
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- Solvent-free reduction of carboxylic acids to alcohols with NaBH4 promoted by 2,4,6-trichloro-1,3,5-triazine and PPh3 in the presence of K2CO3
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A simple, rapid, and eco-friendly method for NaBH4 reduction of carboxylic acids to alcohols under solvent-free conditions was developed using a combination of 2,4,6-trichloro-1,3,5-triazine (TCT) with a catalytic amount of triphenylphosphine as an acid activator. With the 1 : 0.2 : 1.5 : 2 mole ratio of TCT : PPh3 : K2CO3 : NaBH4, carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids (Fmoc, Z) could readily undergo reduction to give the corresponding alcohols in good to excellent yields within 10 min.
- Jaita, Subin,Kaewkum, Pantitra,Duangkamol, Chuthamat,Phakhodee, Wong,Pattarawarapan, Mookda
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p. 46947 - 46950
(2014/12/10)
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- Tailoring of integrin ligands: Probing the charge capability of the metal ion-dependent adhesion site
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Intervention in integrin-mediated cell adhesion and integrin signaling pathways is an ongoing area of research in medicinal chemistry and drug development. One key element in integrin-ligand interaction is the coordination of the bivalent cation at the me
- Bollinger, Markus,Manzenrieder, Florian,Kolb, Roman,Bochen, Alexander,Neubauer, Stefanie,Marinelli, Luciana,Limongelli, Vittorio,Novellino, Ettore,Moessmer, Georg,Pell, Reinhard,Lindner, Wolfgang,Fanous, Joseph,Hoffman, Amnon,Kessler, Horst
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experimental part
p. 871 - 882
(2012/03/26)
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- Solid-phase synthesis of 2-aminoethyl glucosamine sulfoforms
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Mono- and disaccharides of sulfonated glucosamines (GlcN sulfoforms) conjugated to 2-aminoethyl linkers were generated by solid-phase synthesis. Orthogonally protected intermediates were tethered onto tritylated polystyrene resin beads, subjected to amodular sequence of deprotection and sulfonation steps, then cleaved from solid support without degradation of N- or O-sulfate esters using solvolytic conditions, and finally purified by reverse-phase HPLC to afford the title compounds. Copyright Taylor & Francis Group, LLC.
- Liu, Runhui,Wei, Alexander
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experimental part
p. 384 - 419
(2012/08/07)
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- An efficient and expeditious Fmoc protection of amines and amino acids in aqueous media
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A new and environmentally friendly Fmoc protection of a variety of aliphatic and aromatic amines, amino acids, amino alcohols and amino phenols is reported in aqueous media under mild and catalyst-free conditions. The reaction proved to be chemoselective in presence of ambident nucleophiles.
- Gawande, Manoj B.,Branco, Paula S.
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supporting information; experimental part
p. 3355 - 3359
(2012/01/06)
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- CHEMICAL LINKERS AND CLEAVABLE SUBSTRATES AND CONJUGATES THEREOF
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The present disclosure provides drug-ligand conjugates and drug-cleavable substrate conjugates that are potent cytotoxins. The disclosure is also directed to compositions containing the drug-ligand conjugates, and to methods of treatment using them.
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Page/Page column 87
(2010/06/19)
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- A simple synthesis of N β-Fmoc/Z-amino alkyl thiols and their use in the synthesis of N β-Fmoc/Z-amino alkyl sulfonic acids
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A simple and efficient protocol for the synthesis of Nβ- Fmoc/Z-amino alkyl thiols is described. The approach uses sodium pyrosulfite-mediated hydrolysis of isothiouronium salts resulting from the reaction between N-protected aminoalkyl iodides and thiourea. N-Protected taurines were prepared through performic acid oxidation of the thiols and the products were further utilized for the synthesis of dipeptidosulfonamides. Georg Thieme Verlag Stuttgart - New York.
- Sureshbabu,Vishwanatha,Vasantha
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body text
p. 1037 - 1042
(2010/07/06)
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- Synthesis of peptide alcohols on the basis of an O-N acyl-transfer reaction
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(Figure Presented) Getting the better of troublemakers: C-terminal peptide alcohols cannot be synthesized by conventional solidphase peptide synthesis (SPPS) because of the absence of a free carboxylic group to attach to the resin. This problem was circumvented by anchoring a β-amino alcohol residue to the resin to provide a starting point for SPPS. An intramolecular O-N acyl shift completed the synthesis of the desired peptides (see scheme).
- Tailhades, Julien,Gidel, Marie-Aude,Grossi, Benjamin,Lecaillon, Jennifer,Brunel, Luc,Subra, Gilles,Martinez, Jean,Amblard, Muriel
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scheme or table
p. 117 - 120
(2010/04/04)
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- N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides
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(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.
- Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.
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supporting information; experimental part
p. 5260 - 5266
(2009/12/06)
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- Efficient synthesis of N-fmoc-aminoalkoxy pentafluorophenyl carbonates: Application for the synthesis of oligopeptidyl carbamates
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N-Fmoc-Aminoalkoxy pentafluorophenyl carbonates have been synthesized through the reaction of N-Fmoc-aminoalkoxy carbonyl chloride with pentafluorophenol. The reaction was clean and high yielding, and the products have been fully characterized using infra
- Sureshbabu, Vommina V.,Hemantha
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body text
p. 3555 - 3566
(2009/12/26)
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- Efficient loading of primary alcohols onto a solid phase using a trityl bromide linker
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The Letter describes an improved, rapid and mild strategy for the loading of primary alcohols onto a polystyrene trityl resin via a highly reactive trityl bromide linker. This protocol facilitates an efficient resin loading even of acid-sensitive or heat-
- Crestey, Fran?ois,Ottesen, Lars K.,Jaroszewski, Jerzy W.,Franzyk, Henrik
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body text
p. 5890 - 5893
(2009/04/05)
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- A practical and efficient approach to PNA monomers compatible with Fmoc-mediated solid-phase synthesis protocols
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A straightforward synthesis of orthogonally protected PNA monomers is described. Protected aminoethylglycine (Aeg) monomers were efficiently prepared by reductive amination of N-Fmoc-glycinaldehyde with glycine methyl ester and the subsequent acylation of
- Porcheddu, Andrea,Giacomelli, Giampaolo,Piredda, Ivana,Carta, Mariolino,Nieddu, Giammario
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experimental part
p. 5786 - 5797
(2009/06/08)
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- Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases
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Seven PNA-encoded combinatorial libraries targeting proteases and phosphatases with covalent reversible and irreversible mechanism-based inhibitors were prepared. The libraries were synthesized using modified PNA monomers, which dramatically increase the water solubility of the libraries in biologically relevant buffers. The libraries were shown to selectively inhibit targeted enzymes.
- Debaene, Fran?ois,Da Silva, Julien A.,Pianowski, Zbigniew,Duran, Fernando J.,Winssinger, Nicolas
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p. 6577 - 6586
(2008/02/05)
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- Synthesis of radiolabeled sugar metal complexes
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The invention provides a method for manufacturing or preparing neutral, low molecular weight 99mTc-labeled and 186Re-labeled carbohydrate complexes with an improved radiochemical yield from a simple functionalized sugar, such as glucosamine. In particular the synthesis relies on single ligand transfer (SLT) or double ligand transfer (DLT) reactions for converting a ferrocene compound into a rhenium or technetium tricarbonyl complex. The ferrocene compound may be linked to a sugar through various functional groups including, for example, thio, amino and alcohol functionalities to provide a wide range of radiolabeled sugar complexes that include both water soluble and relatively water insoluble compounds.
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Page/Page column 7; 24
(2008/06/13)
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- 3-ETHER AND 3-THIOETHER SUBSTITUTED CYCLOSPORIN DERIVATIVES FOR THE TREATMENT AND PREVENTION OF HEPATITIS C INFECTION
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This invention relates to cyclosporin derivatives of general formula (I) wherein A, B, R1,R2 and X are as defined in the specification, and pharmaceutical compositions prepared from the same, for use in treatment of hepatitis C virus
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Page/Page column 40
(2010/10/20)
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- PEG-POLYACETAL DIBLOCK AND TRIBLOCK COPOLYMERS AND PHARMACEUTICAL COMPOSITIONS
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This invention relates to block copolymer delivery vehicles comprising a polyethyleneglycol-polyacetal, and to controlled release pharmaceutical compositions comprising the delivery vehicle and an active agent. The block copolymers of the invention may be thermogel block copolymers. The pharmaceutical compositions may be in the form of a topical, syringable, or injectable formulation for local controlled delivery of the active agent.
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Page/Page column 50
(2008/06/13)
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- New nonnucleoside substrates for terminal deoxynucleotidyl transferase: Synthesis and dependence of substrate properties on structure
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N-(9-Fluorenylmethoxycarbonyl)-ω-aminoalkyl-, N-(9- fluorenylmethoxycarbonyl)-8-amino-3,6-dioxaoctyl, and N-[(9- fluorenylmethoxycarbonyl)-6-aminohexanoyl]-2-aminoethyl triphosphates were synthesized. All of them were shown to be the substrates of the cal
- Khandazhinskaya,Kukhanova,Jasko
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p. 352 - 356
(2008/02/03)
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- Phosphonomonoester nucleic acids, process for their preparation, and their use
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Novel oligonucleotide analogs of the formula (I) are described, STR1 in which A, B, D, G, L, P, Q, Q', R5, R6, X, Y, Z and n are as defined in the description, which have useful physical, biological and pharmacological properties, as
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- Drug delivery agents incorporating mitomycin
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A conjugate of a carrier polymer and aziridine ring containing mitomycin (MMC) drug molecules is prepared by coupling the MMC molecules via their aziridine imino groups to spacer groups that terminate in protected amino groups, deprotecting said amino groups, recovering and purifying the spacer-MMC derivatives, and then coupling these derivatives via said deprotected amino groups to the carrier polymer. Alternatively, the MMC may first be treated with an activating agent, e.g. carbodiimidazole, to form an activated MMC derivative which is then coupled directly to spacer groups linked to the carrier polymer.
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- Phosphoric acid esters and their use in the preparation of biocompatible surfaces
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A process for the preparation of compounds of formula (I) in which Z is hydrogen or --NHZ is an activated amine group capable of reacting with a surface, the groups R are the same or different and each is a straight or branched C1 -C4 alkyl group, preferably methyl, n is from 2 to 6, and X is a straight or branched C1-20 alkylene group, or X is a group of formula --(CH2 CH2 O)b --, or --(CH2)c --Ar--(CH2)d -- where b is from 1 to 20, c and d are the same or different and each is from 0 to 5, and Ar is a para- or meta- disubstituted phenyl group (preferably a para-disubstituted phenyl group) which is optionally further substituted by one or more C1 -C4 alkyl groups, or an acid addition salt thereof or a hydrate thereof, new compounds of formula (I) and salts and hydrates thereof and the use of compounds of formula (I) and salts and hydrates thereof in treating surfaces to render them more biocompatible.
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- Synthesis of triple helix forming oligonucleotides with a stretched phosphodiester backbone
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Total synthesis of novel DMT-phosphoramidites of thymidine (11 and 15) and 2'-deoxyguanosine (8 and 20) have been accomplished. The utility of these modified building blocks in the preparation of triple helix forming oligodeoxyribonucleotides with a stret
- Rao,Jayaraman,Durland,Revankar
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p. 255 - 273
(2007/10/02)
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- Synthesis of Triple Helix Forming Oligonucleotides with a Stretched Phosphodiester Backbone
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Total synthesis of novel DMT-phosphoramidites of thymidine (11 and 15) and 2'-deoxyguanosine (8 and 20), and their utility in the preparation of triple helix forming oligodeoxyribonucleotides with a stretched phosphodiester backbone are described.
- Rao, T. Sudhakar,Jayaraman, K.,Revenkar, Ganapathi R.
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p. 6189 - 6192
(2007/10/02)
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