Preparation of long-chain acyl thioesters - thio wax esters - by the use of lipases

被引：22

作者：

Weber, N ^{[1
]}

Klein, E ^{[1
]}

Vosmann, K ^{[1
]}

Mukherjee, KD ^{[1
]}

机构：

[1] Fed Ctr Cereal Potato & Lipid Res, HP Kaufmann Inst, Inst Biochem & Technol Lipids, D-48147 Munster, Germany

来源：

BIOTECHNOLOGY LETTERS | 1998年 / 20卷 / 07期

关键词：

D O I：

10.1023/A:1005326725109

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

Long-chain acyl thioesters have been prepared by lipase-catalyzed thioesterification of lauric, myristic, palmitic and stearic acids with decanethiol, dodecanethiol, tetradecanethiol, hexadecanethiol and octadecanethiol. Lipase from Candida antarctica was more effective than that from Rhizomucor miehei. The extent of thioesterification increased with increasing chain length of the fatty acids and decreasing chain length of the alkanethiols. Lipase-catalyzed transthioesterification of fatty acid methyl esters with alkanethiols was less effective than thioesterification for the preparation of acyl thioesters.

引用

页码：687 / 691

页数：5

共 17 条

[1] COBALT(II) CHLORIDE CATALYZED COUPLING OF THIOLS AND ANHYDRIDES - A NEW AND EFFICIENT SYNTHESIS OF THIOL ESTERS [J].

AHMAD, S ;

IQBAL, J .

TETRAHEDRON LETTERS, 1986, 27 (32) :3791-3794

[2] LIPASE-CATALYZED STEREOSELECTIVE THIOTRANSESTERIFICATION OF MERCAPTO ESTERS [J].

BIANCHI, D ;

CESTI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5657-5659

[3]

Caussette M, 1997, J CHEM TECHNOL BIOT, V68, P257, DOI 10.1002/(SICI)1097-4660(199703)68:3<257::AID-JCTB619>3.0.CO

[4]

2-M

[5] Lipase synthesis of short-chain flavour thioesters in solvent-free medium [J].

Cavaille-Lefebvre, D ;

Combes, D .

BIOCATALYSIS AND BIOTRANSFORMATION, 1997, 15 (04) :265-279

[6] S-ETHYL THIOOCTANOATE AS ACYL DONOR IN LIPASE CATALYZED RESOLUTION OF SECONDARY ALCOHOLS [J].

FRYKMAN, H ;

OHRNER, N ;

NORIN, T ;

HULT, K .

TETRAHEDRON LETTERS, 1993, 34 (08) :1367-1370

[7] A MILD AND EFFICIENT SYNTHESIS OF THIOLESTERS FROM ALCOHOLS [J].

GAUTHIER, JY ;

BOURDON, F ;

YOUNG, RN .

TETRAHEDRON LETTERS, 1986, 27 (01) :15-18

[8]

IMAMOTO T, 1982, SYNTHESIS-STUTTGART, P134

[9] EFFICIENT CONVERSION OF CARBOXYLIC-ACIDS INTO THIOL ESTERS [J].

KUNIEDA, T ;

ABE, Y ;

HIROBE, M .

CHEMISTRY LETTERS, 1981, (10) :1427-1428

[10] Aptitude of cheese bacteria for volatile S-methyl thioester synthesis .2. Comparison of coryneform bacteria, Micrococcaceae and some lactic acid bacteria starters [J].

Lamberet, G ;

Auberger, B ;

Bergere, JL .

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1997, 48 (03) :393-397

← 1 2 →