On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2.

被引：11

作者：

Danieli, B

Peri, F

Roda, G

Carrea, G

Riva, S

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, CNR, Ctr Studio Sostanze Organ Nat, I-20133 Milan, Italy

[2] CNR, Ist Biocatalisi & Riconoscimento Mol, I-20131 Milan, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(98)01217-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：2045 / 2060

页数：16

相关论文

共 19 条

[1] ENZYME CATALYZED PREPARATION OF 6-O-ACYLGLUCOPYRANOSIDES [J].

ADELHORST, K ;

BJORKLING, F ;

GODTFREDSEN, SE ;

KIRK, O .

SYNTHESIS-STUTTGART, 1990, (02) :112-115

[2] On the regioselective acylation of 1,6-anhydro-β-D- and L-hexopyranoses catalysed by lipases:: Structural basis and synthetic applications [J].

Boissière-Junot, N ;

Tellier, C ;

Rabiller, C .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1998, 17 (01) :99-115

[3] APPLICATION OF PROTEASE-CATALYZED REGIOSELECTIVE ESTERIFICATION IN SYNTHESIS OF 6'-DEOXY-6'-FLUOROLACTOSIDE AND 6-DEOXY-6-FLUOROLACTOSIDE [J].

CAI, SP ;

HAKOMORI, S ;

TOYOKUNI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3431-3437

[4] CHEMOENZYMATIC SYNTHESIS OF LINEAR POLY(SUCROSE ACRYLATE) - OPTIMIZATION OF ENZYME-ACTIVITY AND POLYMERIZATION CONDITIONS [J].

CHEN, XM ;

JOHNSON, A ;

DORDICK, JS ;

RETHWISCH, DG .

MACROMOLECULAR CHEMISTRY AND PHYSICS, 1994, 195 (11) :3567-3578

[5] REGIOSELECTIVE ACYLATION OF 6-DEOXY-L-HEXOSIDES AND 6-DEOXY-D-HEXOSIDES THROUGH LIPASE-CATALYZED TRANSESTERIFICATION - ENHANCED REACTIVITY OF THE 4-OH FUNCTION IN THE L SERIES [J].

CIUFFREDA, P ;

COLOMBO, D ;

RONCHETTI, F ;

TOMA, L .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :4187-4190

[6] ACYLATION OF 6-DEOXY-L-HEXOSES - REGIOSELECTIVITY IN THE ENZYMATIC TRANSESTERIFICATION AS COMPARED TO CHEMICAL ESTERIFICATION [J].

CIUFFREDA, P ;

RONCHETTI, F ;

TOMA, L .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (01) :125-129

[7] ENZYME KINETICS [J].

CLELAND, WW .

ANNUAL REVIEW OF BIOCHEMISTRY, 1967, 36 :77-+

[8] GLYCOSIDES .1. NEW SYNTHESIS OF 1,2-TRANS O-ARYL GLYCOSIDES, VIA TRIBUTYLTIN PHENOXIDES [J].

CLERICI, F ;

GELMI, ML ;

MOTTADELLI, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :985-988

[9] ENZYMATIC ACYLATION OF METHYL D-GLUCOPYRANOSIDES AND L-GLUCOPYRANOSIDES AND 6-DEOXY-GLUCOPYRANOSIDES [J].

COLOMBO, D ;

RONCHETTI, F ;

SCALA, A ;

TOMA, L .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (01) :89-94

[10] ENZYMATIC ACYLATION OF SUGARS - RATIONALE OF THE REGIOSELECTIVE BUTYRYLATION OF SECONDARY HYDROXY-GROUPS OF D-GALACTO AND L-GALACTO AND MANNOPYRANOSIDES [J].

COLOMBO, D ;

RONCHETTI, F ;

TOMA, L .

TETRAHEDRON, 1991, 47 (01) :103-110