Observations on chemical and enzymatic approaches to α-2,3-sialylated octyl β-lactoside

被引：20

作者：

Turnbull, WB

Harrison, JA

Kartha, KPR

Schenkman, S

Field, RA

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

[2] Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland

[3] Escola Paulista Med, Disciplina Biol Celular, BR-04023062 Sao Paulo, Brazil

来源：

TETRAHEDRON | 2002年 / 58卷 / 16期

基金：

英国医学研究理事会; 英国生物技术与生命科学研究理事会; 英国惠康基金;

关键词：

trans-sialidase; synthesis; biotransformations;

D O I：

10.1016/S0040-4020(02)00265-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

A comparison of chemical and chemo-enzymatic syntheses of alpha-2,3-sialylated octyl lactoside is reported. The chemical approach, starting from lactose and sialic acid, required 14 steps and proceeded in 5% overall yield; poor a-selectivity in the sialylation step necessitated a difficult and low yielding separation of anomers. A chemoenzymatic approach, employing recombinant Trypanosoma cruzi trans-sialidase to effect the key sialylation reaction, required 10 steps and gave a similar overall yield. Whereas the chemo-enzymatic synthesis required only three chromatographic purification steps overall, the chemical synthesis required at least nine. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3207 / 3216

页数：10

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