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 8 条

[1] IDENTIFICATION OF 2 METABOLITES INDUCED BY A BUTYROLACTONE AUTOREGULATOR IM-2 IN STREPTOMYCES SP FRI-5
NAKAMURA, T
NIHIRA, T
YAMADA, Y
FEMS MICROBIOLOGY LETTERS, 1994, 124 (03) : 307 - 313
[2] IM-2, A BUTYROLACTONE AUTOREGULATOR, INDUCES PRODUCTION OF SEVERAL NUCLEOSIDE ANTIBIOTICS IN STREPTOMYCES SP FRI-5
HASHIMOTO, K
NIHIRA, T
SAKUDA, S
YAMADA, Y
JOURNAL OF FERMENTATION AND BIOENGINEERING, 1992, 73 (06): : 449 - 455
[3] Cloning and characterization of the gene (farA) encoding the receptor for an extracellular regulatory factor (IM-2) from Streptomyces sp. strain FRI-5
Waki, M
Nihira, T
Yamada, Y
JOURNAL OF BACTERIOLOGY, 1997, 179 (16) : 5131 - 5137
[4] PURIFICATION AND CHARACTERIZATION OF THE IM-2-BINDING PROTEIN FROM STREPTOMYCES SP STRAIN FRI-5
RUENGJITCHATCHAWALYA, M
NIHIRA, T
YAMADA, Y
JOURNAL OF BACTERIOLOGY, 1995, 177 (03) : 551 - 557
[5] SYNTHESIS OF (R)-5-(HYDROXYMETHYL)-3-ISOPROPYLOXAZOLIDIN-2-ONE AND (S)-5-(HYDROXYMETHYL)-3-ISOPROPYLOXAZOLIDIN-2-ONE, INTERMEDIATES IN THE PREPARATION OF OPTICALLY-ACTIVE BETA-BLOCKERS
WARMERDAM, EGJC
BRUSSEE, J
VANDERGEN, A
KRUSE, CG
HELVETICA CHIMICA ACTA, 1994, 77 (01) : 252 - 256
[6] PREPARATION OF OPTICALLY-ACTIVE DERIVATIVES OF (1,4/2,3,5)-5-AMINOCYCLOPENTANE-1,2,3,4-TETRAOL AND (1,2,3,4,5/0)-5-AMINOCYCLOPENTANE-1,2,3,4-TETRAOL - SYNTHESIS OF MANNOSTATIN A AND ITS ENANTIOMER
OGAWA, S
KIMURA, H
UCHIDA, C
OHASHI, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13): : 1695 - 1705
[7] PHEROMONE SYNTHESIS .37. PREPARATION OF THE BOTH ENANTIOMERS OF THREO-2-AMINO-3-METHYLHEXANOIC ACID BY ENZYMATIC RESOLUTION AND THEIR CONVERSION TO OPTICALLY-ACTIVE FORMS OF THREO-4-METHYLHEPTAN-3-OL, A PHEROMONE COMPONENT OF THE SMALLER EUROPEAN ELM BARK BEETLE
MORI, K
IWASAWA, H
TETRAHEDRON, 1980, 36 (15) : 2209 - 2213
[8] SEPARATION OF OPTICAL ISOMERS OF (+/)-3-CARBOXY-4-OXO-6-METHYL-6,7,8,9-TETRAHYDRO-4H-PYRIDO(1,2-ALPHA)PYRIMIDINE AND DL-THREO-1-(PARA-NITROPHENYL)-2-AMINO-PROPANEDIOL-1,3 BY MUTUAL-RESOLUTION .2. PREPARATION OF OPTICAL ISOMERS OF DL-THREO-1-(PARA-NITROPHENYL)-2-AMINO-PROPANEDIOL USING OPTICALLY-ACTIVE 3-CARBOXY-4-OXO-6-METHYL-6,7,8,9-TETRAHYDRO-4H-PYRIDO(1,2-ALPHA)PYRIMIDINEN
FOGASSY, E
ACS, M
HERMECZ, I
MATHE, I
PERIODICA POLYTECHNICA-CHEMICAL ENGINEERING, 1977, 21 (02) : 229 - 235

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