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

Bhaswati Ghosh, Nabarupa Bhattacharjee, Ananda Rao Podilapu, Krishna Puri, Suvarn S. Kulkarni

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Abstract

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.

Original languageEnglish
Pages (from-to)3696-3701
Number of pages6
JournalOrganic Letters
Volume24
Issue number20
DOIs
StatePublished - May 27 2022
Externally publishedYes

Funding

S.S.K. thanks the Science and Engineering Research Board, Department of Science and Technology, Government of India (Grants CRG/2019/000025 and SPR/2021/000328) for financial support. A.R.P. and K.P. thank UGC New Delhi for research fellowships. B.G. thanks IIT Bombay for an Institute Post-Doctoral fellowship.

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