Click Chemistry Aided Synthesis of 1,4-Substituted 1,2,3-Triazole Based N-Fmoc Protected ε-Amino Acids: Isolation, Characterization and Synthesis of Novel Triazole Based Unnatural Amino Acids

被引:9
|
作者
Sureshbabu, Vommina V. [1 ]
Narendra, N. [1 ]
Hemantha, H. P. [1 ]
Chennakrishnareddy, G. [1 ]
机构
[1] Bangalore Univ, Dept Studies Chem, Peptide Res Lab, Bangalore 560001, Karnataka, India
来源
PROTEIN AND PEPTIDE LETTERS | 2010年 / 17卷 / 04期
关键词
Click reaction; 1,2,3-Triazole; 3+2 cycloaddition; unnatural amino acid; Fmoc-chemistry; SOLID-PHASE SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; COPPER-CATALYZED SYNTHESIS; ONE-POT SYNTHESIS; BETA-TURN MIMICS; 1,3-DIPOLAR CYCLOADDITION; BIOLOGICAL EVALUATION; CYCLODEXTRIN ANALOGS; CARBOHYDRATE; MULTIVALENT;
D O I
10.2174/092986610790963735
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A new class of 1,4-substituted 1,2,3-triazole-based unnatural amino acids is demonstrated by employing click reaction between N-Fmoc amino alkyl azides and propiolic acid. The resulting unnatural amino acids were isolated and then subjected to Fmoc deprotection to isolate 1,2,3-triazole based amino acids as stable solids. These new class of molecules were also used for chain extension from both N- and C-terminals to synthesize dipeptidomimetics bearing 1,2,3-triazole moiety in the backbone.
引用
收藏
页码:499 / 506
页数:8
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