SYNTHESES OF 2-[(1S,3S)-1-AMINO-3-CARBOXY-3-HYDROXYPROPYL]-THIAZOLE-4-CARBOXYLIC ACID AND THE TRIPEPTIDE SKELETON OF NOSIHEPTIDE CONTAINING THE ACID

被引：23

作者：

SHIN, CG ^{[1
]}

NAKAMURA, Y ^{[1
]}

YAMADA, Y ^{[1
]}

YONEZAWA, Y ^{[1
]}

UMEMURA, K ^{[1
]}

YOSHIMURA, J ^{[1
]}

机构：

[1] IWAKI MEISEI UNIV, COLL SCI & TECHNOL, IWAKI, FUKUSHIMA 970, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1995年 / 68卷 / 11期

关键词：

D O I：

10.1246/bcsj.68.3151

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselective synthesis of an amino acid component called Fragment D, N,O-diprotected 2-[(1S, 3S)-1-amino-3-carboxy-3-hydroxypropyl]thiazole-4-carboxylic acid of a macrobicyclic peptide antibiotic nosiheptide, was achieved by two routes. The dipeptide, Fragment B-C, 2-[(Z)-1-(N, O-isopropylidene-L-threonylamino)-1-propenyl] thiazole-4-carboxylic acid was also synthesized by the thiazole ring formation from (Z)-2-(N, O-diprotected L-threonylamino)-2-butenethioamide with ethyl bromopyruvate. The coupling of two components by using a condensing agent gave the expected tripeptide 2, which is an important partial skeleton of the nosiheptide.

引用

页码：3151 / 3160

页数：10

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