- A convenient synthesis of azido peptides by post-assembly diazo transfer on the solid phase applicable to large peptides
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An efficient method for the conversion of solid phase bound peptide amines into azides by a diazo transfer using triflyl azide in the presence of divalent copper ions is described. α-Azido acids and azido peptides - up to 30 amino acids in length - are obtained in good yields and high purities after cleavage from the solid support.
- Rijkers, Dirk T.S.,Van Vugt, H.H.Ricardo,Jacobs, Hans J.F.,Liskamp, Rob M.J.
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- Design, Synthesis, and Activity Evaluation of Stereoconfigured Tartarate Derivatives as Potential Anti-inflammatory Agents in Vitro and in Vivo
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Preclinical and clinical data reveal that inflammation is strongly correlated with the pathogenesis of a number of diseases including those of cancer, Alzheimer, and diabetes. The inflammatory cascade involves a multitude of cytokines ending ultimately with the activation of COX-2/LOX for the production of prostaglandins and leukotrienes. While the available inhibitors for these enzymes suffer from nonoptimal selectivity, in particular for COX-2, we present here the results of purposely designed tartarate derivatives that exhibit favorable selectivity and significant effectiveness against COX-2 and LOX. Integrated approaches of molecular simulation, organic synthesis, and biochemical/physical experiments identified 15 inhibiting COX-2 and LOX with respective IC50 4 and 7 nM. At a dose of 5 mg kg-1 to Swiss albino mice, 15 reversed algesia by 65% and inflammation by 33% in 2-3 h. We find good agreement between experiments and simulations and use the simulations to rationalize our observations.
- Kumari, Priya,Singh, Palwinder,Kaur, Jashanpreet,Bhatti, Rajbir
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- Concise synthesis of: N -phosphorylated amides through three-component reactions
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N-Phosphorylated amides continue to be an unparalleled asset for the development of pharmaceutical molecules, and the importance of this framework has inspired researchers to look for concise and efficient methods for the synthesis of this unit. In this work, a new strategy was developed in which a one-pot synthesis of N-phosphorylated amides was achieved by a three-component reaction with carboxylic acids, phosphorus chlorides and azides under mild reaction conditions. To our knowledge, this is the first study in which this framework was constructed through a multicomponent reaction, which is innovative, efficient and economical. This journal is
- Yang, Shang-Dong,Zhang, Tao,Zhou, Linlin,Zhu, Yuan-Yuan
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supporting information
p. 9417 - 9421
(2021/12/09)
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- Glycerol conversion to high-value chemicals: The implication of unnatural α-amino acid syntheses using natural resources
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Glycerol derivatives are an important class of compounds, which have great applications as basic structural building blocks in organic synthesis. O-Benzylglycerol was oxidised to produce a high-value compound in high yield using a NaOtBu-O2 system. Furthermore, the synthetic utility of the resulting product was demonstrated by its transformation into unnatural α-amino acids, thus showing the valorisation of glycerol biomass.
- Park, Yun Ji,Yang, Jung Woon
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p. 2615 - 2620
(2019/06/03)
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- Synthesis, Absorption, and Fluorescence Studies of Coumaryl-Labelled Amino Acids and Dipeptides Linked Via Triazole Ring
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Fluorophores based on 4-triazolyl, 7-hydroxy-4-triazolylmethyl, 4-O-triazolylmethyl, and 7-O-triazolylmethyl coumaryl-tagged amino acids and dipeptides were synthesized by copper-catalyzed [3+2] cycloaddition reaction between azido- or alkynyl-functionalized coumarins with alkynyl- or azido-functionalized amino acid and dipeptides in good-to-excellent yields. Steady-state absorption and the fluorescence properties of the synthesized conjugates were studied. The chemical applicability of these amino acid and peptide-based fluorophores was successfully demonstrated by their linear elongation by further tagging them with appropriate C- or N-terminus amino acid.
- Kumari, Santosh,Joshi, Sunita,Shakoor, S.M. Abdul,Agarwal, Devesh S.,Panda, Siva S.,Pant, Debi D.,Sakhuja, Rajeev
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p. 1415 - 1426
(2015/09/15)
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- SELECTIVE HISTONE DEACETYLASE 8 INHIBITORS
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Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of histone deacetylase 8 (HDAC8). Also described herein are methods of using such HDAC8 inhibitors, alone and in combination with other co
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Paragraph 00270
(2014/08/07)
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- A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate
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Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. the Partner Organisations 2014.
- Kitamura, Mitsuru,Kato, So,Yano, Masakazu,Tashiro, Norifumi,Shiratake, Yuichiro,Sando, Mitsuyoshi,Okauchi, Tatsuo
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p. 4397 - 4406
(2014/06/23)
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- A unique and rapid approach toward the efficient development of novel protein tyrosine phosphatase (PTP) inhibitors based on 'clicked' pseudo-glycopeptides
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There has been considerable interest in the development of protein tyrosine phosphatase (PTP) inhibitors since many of the PTP members are tightly associated with major human diseases including autoimmune disorders, diabetes and cancer. We report here a u
- Yang, Jin-Wei,He, Xiao-Peng,Li, Cui,Gao, Li-Xin,Sheng, Li,Xie, Juan,Shi, Xiao-Xin,Tang, Yun,Li, Jia,Chen, Guo-Rong
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supporting information; experimental part
p. 1092 - 1096
(2011/04/16)
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- 1,2,3-Triazolyl amino acids as AMPA receptor ligands
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The central nervous system glutamate receptors are an important target for drug discovery. Herein we report initial investigations into the synthesis and glutamate receptor activity of 1,2,3-triazolyl amino acids. Two compounds were found to be selective
- Stanley,Pedersen, D. Sejer,Nielsen,Kvist,Mathiesen,Br?uner-Osborne,Taylor,Abell
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supporting information; experimental part
p. 7512 - 7515
(2011/03/17)
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- One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from aldehydes and amines
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A one-pot, three-step synthesis of 1,4-disubstituted 1,2,3-triazoles from aldehyde and amine has been developed by in situ transformation of aldehyde into alkyne, followed by diazo-transfer of amine into azide and subsequent cycloaddition. This procedure allowed the synthesis of fluorescent amino acid derivatives as well as glycoconjugate mimetics. Georg Thieme Verlag Stuttgart.
- Maisonneuve, Stephane,Xie, Juan
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experimental part
p. 2977 - 2981
(2010/01/21)
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- Methods for preparing nonpeptidic oligomers from amino acids
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The present invention relates to nonpeptidic oligomers. Methods for preparing nonpeptidic oligomers from amino acids by replacing the amide bond with heterocyclic rings are also disclosed.
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Page/Page column 10-11; 12
(2008/06/13)
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- Triazolopeptides: chirospecific synthesis and cis/trans prolyl ratios of structural isomers
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As cis/trans prolyl isomerization plays a crucial role in various biological processes, peptide mimics capable of modifying the cis/trans Xaa-Pro ratio are of particular interest. A practical approach toward proline derived triazolopeptides employing [3+2] azide-alkyne cycloadditions as the key reaction step and the analysis of their cis/trans prolyl ratios are reported. Structural investigations indicated the adjustability of both the cis-percentage and the conformational stability toward intramolecular H-bonding effects.
- Paul, Andreas,Bittermann, Holger,Gmeiner, Peter
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p. 8919 - 8927
(2007/10/03)
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- Nonpeptidic foldamers from amino acids: Synthesis and characterization of 1,3-substituted triazole oligomers
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Nonpeptidic foldamers capable of displaying protein-like functionality were prepared by swapping amide bonds with 1,2,3-triazole rings. The overall conformation of these triazole oligomers is largely dictated by dipole-dipole interactions between adjacent
- Angelo, Nicholas G.,Arora, Paramjit S.
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p. 17134 - 17135
(2007/10/03)
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- Preparation of (R)-2-azidoesters from 2-((p-nitrobenzene)sulfonyl)oxy esters and their use as protected amino acid equivalents for the synthesis of di- and tripeptides containing D-amino acid constituents
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(R)-2-Azidoesters and their derived (R)-2-azido acids are readily prepared from common amino acids by an inversion methodology that employs (S)-2-nosyloxyesters as key intermediates. The (R)-2-azidoesters can be used as protected amino acid equivalents in peptide synthesis. Basic hydrolysis frees the carboxyl group. Triphenylphosphine/water is used to free the amine group. By these reactions a variety of L-D and D-L dipeptides, L-D-L tripeptides, and depsipeptides can be prepared easily in good yields, and without detectable epimerization.
- Hoffman,Kim
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p. 3007 - 3020
(2007/10/02)
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- Nucleophilic Substitution Reactions of Alkyl Halides By Using New Polymer-Supported Reagents Containing Hemin
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A new polymer reagent consisting of hemin, divinylbenzene, and 2-methyl-5-vinylpyridine was synthesized by suspension copolymerization.Substitution reactions of primary, secondary, and tertiary alkyl halides with the hemin copolymer combined with cyanide, azide, and thiocyanate ions were given satisfactory yields.This reaction mechanism was revealed to be a SNi type on the basis of stereochemical study.The hemin copolymer was not only a polymer-supported reagent with functional capabilities, but also served to separate the product from the reaction mixture.
- Saito, Kiyoshi,Harada, Kaoru
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p. 2562 - 2566
(2007/10/02)
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