Enantiopure Cα-tetrasubstituted α-amino acids.: Chemoenzymatic synthesis and application to turn-forming peptides

被引：30
|
作者：
Kaptein, B
Broxterman, QB
Schoemaker, HE
Rutjes, FPJT
Veerman, JJN
Kamphuis, J
Peggion, C
Formaggio, F
Toniolo, C
机构：
[1] Univ Padua, CNR, Biopolymer Res Ctr, Dept Organ Chem, I-35131 Padua, Italy
[2] DSM Res & Patents, Organ Chem & Biotechnol Sect, NL-6160 MD Geleen, Netherlands
[3] Univ Nijmegen, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands
[4] Univ Amsterdam, Inst Mol Chem, NL-1018 WS Amsterdam, Netherlands
[5] DSM Food Specialties, Nutrit Ingredients, NL-2600 MA Delft, Netherlands
来源：
TETRAHEDRON | 2001年 / 57卷 / 30期
关键词：
amino acids and derivatives; metathesis; NMR; peptides and polypeptides;
D O I：
10.1016/S0040-4020(01)00548-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By a chemo-enzymatic approach we carried out a large-scale synthesis of four enantiopure, sterically constrained, C-alpha-tetra-substituted alpha -amino acids, all characterized by a sidechain (CCdelta)-C-gamma double bond. By using one of them (L-Mag), we prepared an N-alpha-protected tetrapeptide benzylamide which was shown to adopt a beta -turn conformation and to efficiently undergo ring-closing olefin metathesis. (C) 2001 Elsevier Science Led. All rights reserved.
引用
收藏
页码：6567 / 6577
页数：11
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