Synthesis of LeXand LeYOligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups1
作者:
SantiagoFigueroa Pérez,
RaulGonzález Lio,
VioletaFernández Santana,
VicenteVerez Bencomo,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 6
页码: 835-850
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808007459
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
5-Azido-3-oxa-l-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide β-D-Gal-(1→4)-[α-L-Fuc-(1→3)]-GlcNAc and the tetrasaccharide α-L-Fuc-α-(1→2)-β-D-Gal-(1→4)-[α-L-Fuc-(1→3)]-GlcNAc that represent the epitopes defining the human blood groups Lexand Ley. The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.
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