Synthesis of a Spore Surface Pentasaccharide of  Bacillus anthracis | Zendy

Werz Daniel B. | Zendy; Adibekian Alexander | Zendy; Seeberger Peter H. | Zendy

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Synthesis of a Spore Surface Pentasaccharide of Bacillus anthracis

Author(s) -

Werz Daniel B.,

Adibekian Alexander,

Seeberger Peter H.

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200601082

Subject(s) - chemistry , bacillus anthracis , amine gas treating , rhamnose , protecting group , tributyltin hydride , glycosylation , selectivity , stereochemistry , organic chemistry , biochemistry , bacteria , polysaccharide , genetics , alkyl , biology , catalysis

An analogue 2 of the pentasaccharide 1 found on the spore surface protein BclA of Bacillus anthracis was synthesized by a (3+2) glycosylation approach. A robust building block for 3‐linked α‐rhamnose is presented. Benzoate groups were used to ensure α‐selectivity for the rhamnose units. A radical‐initiated reduction with tributyltin hydride was shown to be able to convert the NHTCA group into an acetylated amine as well as an azido group into a free amine on one strike. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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