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

doi:10.1021/acs.orglett.2c01318

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

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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 language	English
Pages (from-to)	3696-3701
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.2c01318
State	Published - May 27 2022
Externally published	Yes

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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10.1021/acs.orglett.2c01318

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

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.",

author = "Bhaswati Ghosh and Nabarupa Bhattacharjee and Podilapu, \{Ananda Rao\} and Krishna Puri and Kulkarni, \{Suvarn S.\}",

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doi = "10.1021/acs.orglett.2c01318",

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AU - Ghosh, Bhaswati

AU - Bhattacharjee, Nabarupa

AU - Podilapu, Ananda Rao

AU - Puri, Krishna

AU - Kulkarni, Suvarn S.

PY - 2022/5/27

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AB - 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.

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ER -

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

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