SYNTHESIS OF MODIFIED PARTIAL STRUCTURES OF THE BACTERIAL-CELL WALL .1. LIPOPEPTIDES CONTAINING NONPROTEINOGENIC AMINO-ACIDS

被引：22

作者：

SCHNEIDER, H ^{[1
]}

SIGMUND, G ^{[1
]}

SCHRICKER, B ^{[1
]}

THIRRING, K ^{[1
]}

BERNER, H ^{[1
]}

机构：

[1] SANDOZ GMBH,BRUNNERSTR 59,A-1235 VIENNA,AUSTRIA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 03期

关键词：

D O I：

10.1021/jo00055a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences. The ene reaction of the alpha-allylated dipeptide 12 with butyl glyoxylate was used as a key step. The required enantiomerically pure substrates 9, 10, and 23 were obtained by enzymatic hydrolysis of the corresponding racemic alpha-allylated esters. The absolute configuration of both stereoisomers 1 and 2 was assigned by oxidative cleavage of the double bond in 18 and 19 followed by comparison of the esterified degradation products 28 and 29 with samples of authentic configuration, derived from (R)- and (S)-malic acid.

引用

页码：683 / 689

页数：7

共 18 条

[11]

SCHOLLKOPF U, 1981, SYNTHESIS-STUTTGART, P966

[12] ALPHA-CHYMOTRYPSIN CATALYZED ENANTIOSELECTIVE HYDROLYSIS OF ALKENYL-ALPHA-AMINO ACID-ESTERS [J].