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Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae.

ABSTRACT: A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been synthesized using a D-mannose-derived thioglycoside by a two-step activation process. Late stage TEMPO-mediated oxidation of the pentasaccharide derivative using phase-transfer reaction conditions furnished the target compound in satisfactory yield.

SUBMITTER: Gucchait A

PROVIDER: S-EPMC6404407 | biostudies-other | 2019

REPOSITORIES: biostudies-other

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Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae.

Gucchait Arin A Ghosh Angana A Misra Anup Kumar AK

Beilstein journal of organic chemistry 20190213

A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been synthesized using a D-mannose-derived thioglycoside by a two-step activation process. Late stage TEMPO-mediated oxidation of the pentasaccharide derivative using phase-transfer reaction condition ...[more]

PMID: 30873227

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