Abstract
The powerful chemo-enzymatic synthesis of the pentadecasaccharide hapten involved in the first synthetic carbohydrate-based vaccine candidate against endemic shigellosis is reported. The high yielding site-selective α-D-glucosylation of a lightly protected disaccharide by an engineered transglucosylase-sucrose system gave a trisaccharide, which was chemically elongated by an efficient [5+5] process.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Bacterial Vaccines / biosynthesis*
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Bacterial Vaccines / chemical synthesis*
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Bacterial Vaccines / chemistry
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Carbohydrate Conformation
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Carbohydrate Sequence
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Dysentery, Bacillary / prevention & control*
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Glucosyltransferases / chemistry
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Glucosyltransferases / metabolism*
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Glycosylation
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Haptens / biosynthesis
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Haptens / chemistry
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Molecular Sequence Data
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Oligosaccharides / biosynthesis*
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Oligosaccharides / chemical synthesis*
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Oligosaccharides / chemistry
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Sucrose / chemistry*
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Sucrose / metabolism
Substances
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Bacterial Vaccines
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Haptens
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Oligosaccharides
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Sucrose
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Glucosyltransferases