ENZYMATIC RESOLUTION OF 2-ACYL-3-HYDROXYMETHYL-4-BUTANOLIDE AND PREPARATION OF OPTICALLY-ACTIVE IM-2, THE AUTOREGULATOR FROM STREPTOMYCES SP FRI-5

被引：29

作者：

MIZUNO, K ^{[1
]}

SAKUDA, S ^{[1
]}

NIHIRA, T ^{[1
]}

YAMADA, Y ^{[1
]}

机构：

[1] OSAKA UNIV,FAC ENGN,DEPT BIOTECHNOL,SUITA,OSAKA 565,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 37期

关键词：

D O I：

10.1016/S0040-4020(01)85697-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Racemic 2-acyl-3-hydroxymethyl-4-butanolides were resolved through a lipase-catalyzed acylation with acetic anhydride. Optically active forms of 2-butyryl-3-hydroxymethyl-4-butanolide 14 obtained were used to prepare enantiomers of IM-2 10, the autoregulator from Streptomyces sp. FRI-5. The absolute configuration of IM-2 was deduced to be (2R,3R,6R).

引用

页码：10849 / 10858

页数：10

共 16 条

[1] ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS [J].

BIANCHI, D ;

CESTI, P ;

BATTISTEL, E .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5531-5534

[2] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[3] INTERSPECIFIC INDUCERS OF CYTODIFFERENTIATION AND ANTHRACYCLINE BIOSYNTHESIS FROM STREPTOMYCES-BIKINENSIS AND STREPTOMYCES-CYANEOFUSCATUS [J].

GRAFE, U ;

REINHARDT, G ;

SCHADE, W ;

ERITT, I ;

FLECK, WF ;

RADICS, L .

BIOTECHNOLOGY LETTERS, 1983, 5 (09) :591-596

[4] A NEW INDUCER OF ANTHRACYCLINE BIOSYNTHESIS FROM STREPTOMYCES-VIRIDOCHROMOGENES [J].

GRAFE, U ;

SCHADE, W ;

ERITT, I ;

FLECK, WF .

JOURNAL OF ANTIBIOTICS, 1982, 35 (12) :1722-1723

[5]

KLEINER EM, 1976, BIOORG KHIM+, V2, P1142

[6] NEW VIRGINIAE BUTANOLIDES FROM STREPTOMYCES-VIRGINIAE [J].

KONDO, K ;

HIGUCHI, Y ;

SAKUDA, S ;

NIHIRA, T ;

YAMADA, Y .

JOURNAL OF ANTIBIOTICS, 1989, 42 (12) :1873-1876

[7]

MORI K, 1990, LIEBIGS ANN CHEM, P31

[8] SYNTHETIC MICROBIAL CHEMISTRY .3. REVISION OF THE ABSOLUTE-CONFIGURATION OF A-FACTOR - THE INDUCER OF STREPTOMYCIN BIOSYNTHESIS, BASING ON THE RECONFIRMED (R)-CONFIGURATION OF (+)-PARACONIC ACID [J].

MORI, K .

TETRAHEDRON, 1983, 39 (19) :3107-3109

[9] STRUCTURE-ACTIVITY-RELATIONSHIPS OF VIRGINIAE BUTANOLIDE-C, AN INDUCER OF VIRGINIAMYCIN PRODUCTION IN STREPTOMYCES-VIRGINIAE [J].

NIHIRA, T ;

SHIMIZU, Y ;

KIM, HS ;

YAMADA, Y .

JOURNAL OF ANTIBIOTICS, 1988, 41 (12) :1828-1837

[10]

OTANI I, 1991, J AM CHEM SOC, V113, P4092

← 1 2 →