Regioselective enzyme-mediated glycosylation of natural polyhydroxy compounds .1. Galactosylation of stevioside and steviolbioside

被引：19

作者：

Danieli, B

Luisetti, M

SchubertZsilavecz, M

Likussar, W

Steurer, S

Riva, S

Monti, D

Reiner, J

机构：

[1] GRAZ UNIV,INST PHARMACEUT CHEM,A-8010 GRAZ,AUSTRIA

[2] CNR,IST CHIM ORMONI,I-20133 MILAN,ITALY

[3] UNIV BAYREUTH,DEPT ORGAN CHEM,D-95447 BAYREUTH,GERMANY

来源：

HELVETICA CHIMICA ACTA | 1997年 / 80卷 / 04期

关键词：

D O I：

10.1002/hlca.19970800412

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bovine beta-1,4-galactosyltransferase is an efficient catalyst for the regioselective transfer of galactose from UPD-galactose, generated in situ with the UDP-glucose/UDP-glucose-4-epimerase system, to the kaurane glycosides stevioside (1) and steviolbioside (2), affording the corresponding galactosyl derivatives 3 and 4 in high yields. By a combination of 2D NMR techniques (COSY, TOCSY, ROESY. HMQC, and HMBC), the structure of the products is established as 13-[(beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl)oxy]kaur-16-en-19-oic acid beta-D-glucopyranosyl ester (3) and 13-[(beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl)oxy]kaur-16-en-19-oic acid (4).

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页码：1153 / 1160

页数：8

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