Enzymatic cleavage of N-phenylacetyl-protected ethanolamine phosphates

被引：0

作者：

vanStraten, NCR ^{[1
]}

Duynstee, HI ^{[1
]}

deVroom, E ^{[1
]}

vanderMarel, GA ^{[1
]}

vanBoom, JH ^{[1
]}

机构：

[1] GIST BROCADES,NL-2600 MA DELFT,NETHERLANDS

来源：

LIEBIGS ANNALEN-RECUEIL | 1997年 / 06期

关键词：

L-glycero-alpha-D-manno-heptopyranosides; ethanolamine phosphates; phenylacetyl; enzymatic cleavage of; carbohydrates; glucosylations;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Immobilized penicillin-G acylase mediated removal of the N-phenylacetyl protective group in ethanolamine phosphates 7 and 9 furnished compounds 8 and 10, respectively. Deblocking of N-phenylacetyl-protected ethanolamine phosphate heptosyl disaccharide 22, a protected spacer-containing fragment of the inner-core lipopolysaccharide region of Neisseria meningitidis, immunotype L3 was readily accomplished with penicillin-G acylase, yielding target dimer 2, Disaccharide 22 was accessible by elongation of ethyl 1-thio-L-glycero-alpha-D-manno-heptopyranosyl donor 13 with acceptor 14 under the influence of N-iodosuccinimide/triflic acid. Protective group manipulations, phosphorylation with the reagent 2-cyano-ethyl 2-(phenylacetylamino)ethyl N,N-diisopropylphosphoramidite (5) and deprotection furnished LD-Hepp dimer 22.

引用

页码：1215 / 1220

页数：6

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