Stereoselective synthesis of non symmetric dihydroxyethylene dipeptide isosteres via epoxyalcohols derived from α-amino acids

被引：14

作者：

Benedetti, F

Magnan, M

Miertus, S

Norbedo, S

Parat, D

Tossi, A

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34129 Trieste, Italy

[2] Univ Trieste, Dipartimento Biochim Biofis & Chim Macromol, I-34129 Trieste, Italy

[3] UNIDO, ICS, Area Ric, I-34012 Trieste, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 20期

关键词：

amino acids and derivs; isosteres; stereospecificity; enzyme inhibitors;

D O I：

10.1016/S0960-894X(99)00529-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

(1R,2R,3S, 4S)-4-Amino-3-hydroxy-1,2-epoxybutanes, accessible in four steps from L-aminoesters, react regio- and stereoselectively with diethyl aluminum cyanide to give (1R, 2S, 3S, 4S)-4-amino-2,3-dihydroxynitriles. Hydrolysis yields hydroxylactones equivalent to 2,3-dihydroxy-4-aminoacids. The sequence provides a novel approach to dihydroxyethylene isosteres potentially useful for new HIV-protease inhibitors. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3027 / 3030

页数：4

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