Total Synthesis of the Repeating Units of O‑Specific Polysaccharide of Pseudomonas chlororaphis subsp. aureofaciens UCM B‑306 via One-Pot Glycosylation

Herein we report the first total syntheses of the trisaccharide-repeating units of Pseudomonas chlororaphis subsp. aureofaciens UCM B-306 via a one-pot assembly of the core trisaccharide structure. The rare-sugar-containing trisaccharide-repeating units are comprised of d-bacillosamine, 2-amino-2-de...

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Bibliographic Details
Published in:Organic letters 2022-05, Vol.24 (20), p.3696-3701
Main Authors: Ghosh, Bhaswati, Bhattacharjee, Nabarupa, Podilapu, Ananda Rao, Puri, Krishna, Kulkarni, Suvarn S.
Format: Article
Language:English
Subjects:
Glycosylation
O Antigens - chemistry
Pseudomonas - chemistry
Trisaccharides
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Summary:Herein we report the first total syntheses of the trisaccharide-repeating units of Pseudomonas chlororaphis subsp. aureofaciens UCM B-306 via a one-pot assembly of the core trisaccharide structure. The rare-sugar-containing trisaccharide-repeating units are comprised of d-bacillosamine, 2-amino-2-deoxy-d-galacturonic acid or amide, and d-rhamnose units linked through three consecutive α-linkages. The total syntheses of two repeating units were completed starting from d-mannose via a longest-linear sequence of 27 steps in 5.8% and 4.4% overall yields, respectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01318