Large-scale chemical and enzymatic synthesis of a Clostridium difficile toxin a binding trisaccharide

Trisaccharide 1, 8-methoxycarbonyloctyl-O-(alpha-D-galactopyranosyl)-(1-->3)-(beta-D-galactopyranosyl)-(1-->4)-beta-D-glucopyranoside, linked to a solid support can be used to remove Clostridium diffcile toxin A from the intestinal tract. Therefore, multi-gram chemical and enzymatic synthesis...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 14; pp. 2293 - 2296
Main Authors Ratcliffe, RM, Kamath, VP, Yeske, RE, Gregson, JM, Fang, YR, Palcic, MM
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
iso-globo trisaccharide
HYDROXYL GROUP
Gal(alpha 1,3)Gal epitope
OLIGOSACCHARIDES
FUSION
Clostridium difficile toxin A
TETRASACCHARIDE
galactosyltransferase
CHEMOENZYMATIC SYNTHESIS
CATALYZED SYNTHESIS
LACTOSAMINE
RECEPTOR
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Summary:Trisaccharide 1, 8-methoxycarbonyloctyl-O-(alpha-D-galactopyranosyl)-(1-->3)-(beta-D-galactopyranosyl)-(1-->4)-beta-D-glucopyranoside, linked to a solid support can be used to remove Clostridium diffcile toxin A from the intestinal tract. Therefore, multi-gram chemical and enzymatic synthesis of the toxin binding trisaccharide 1 from 8-methoxycarbonyloctyl beta-lactoside disaccharide 2 were explored. Chemical conversion in 30% overall yield could be achieved in seven steps. Alternatively a single step enzymatic conversion of the lactoside using recombinant a(1-->3)-galactosyltransferase with UDP-galactose or UDP-glucose/UDP-Glc epimerase gave 1 in 85-90% yield.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2004-831188