Synthesis of Haptenic Trimers Corresponding to the Cell Wall Glycopeptidolipids ofMycobacterium AviumSerovar 12
作者:
Korien Zegelaar-Jaarsveld,
SimonC. van der Plas,
GijsA. van der Marel,
JacquesH. van Boom,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1996)
卷期:
Volume 15,
issue 5
页码: 591-610
ISSN:0732-8303
年代: 1996
DOI:10.1080/07328309608005677
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
The preparation of the spacer-containing trimers2, 3-aminopropyl 3-O-[4-O-Me-3-O-(4-N-D,L-lactoyl-3-O-Me-β-D-Quip)-α-L-Rhap]-α-L-Rhap, derivatives of the antigenic determinant of the glycopeptidolipid fromMycobacterium aviumserotype 12, are described. Thus, iodonium ion-mediated glycosylation of the spacer-containing acceptor7with ethyl 1-thio-rhamnopyranoside donor10, followed by selective deprotection of thep-methoxybenzyl group of thus obtained19gave bis-rhamnopyranoside acceptor20. Elongation of20with ethyl 4-azido-1-thio-β-D-quinovopyranoside18and subsequent reduction of the azido function in21led to trimer22. The amino group in22was coupled with both D- and L-lactic acid to give, after removal of the protective groups, trimers2.
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