Synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59: Unexpected stereo outcome in glycosylation

Abhijit Sau; Rajib Panchadhayee; Debjani Ghosh; Anup Kumar Misra

doi:10.1016/j.carres.2012.01.026

Synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59: Unexpected stereo outcome in glycosylation

Abhijit Sau, Rajib Panchadhayee, Debjani Ghosh, Anup Kumar Misra^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

10 Citations (Scopus)

Abstract

Convergent synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59 is presented. A thioglycoside disaccharide donor was prepared by the glycosylation of two thioglycosides by tuning their relative reactivity. An unexpected stereochemical outcome was observed in a glycosylation using an ethyl 2-O-acetyl-3-O-benzyl-4, 6-O-bensylidene-thio-galactoside donor, where the alpha-galactoside was formed in spite of the presence of the 2-O-acetyl participating group.

Original language	English
Pages (from-to)	18-22
Number of pages	5
Journal	Carbohydrate Research
Volume	352
DOIs	https://doi.org/10.1016/j.carres.2012.01.026
Publication status	Published - 1 May 2012

Keywords

Glycosylation
O-Polysaccharide
Salmonella enterica
Stereoselectivity
Tetrasaccharide

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10.1016/j.carres.2012.01.026

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title = "Synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59: Unexpected stereo outcome in glycosylation",

abstract = "Convergent synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59 is presented. A thioglycoside disaccharide donor was prepared by the glycosylation of two thioglycosides by tuning their relative reactivity. An unexpected stereochemical outcome was observed in a glycosylation using an ethyl 2-O-acetyl-3-O-benzyl-4, 6-O-bensylidene-thio-galactoside donor, where the alpha-galactoside was formed in spite of the presence of the 2-O-acetyl participating group.",

keywords = "Glycosylation, O-Polysaccharide, Salmonella enterica, Stereoselectivity, Tetrasaccharide",

author = "Abhijit Sau and Rajib Panchadhayee and Debjani Ghosh and Misra, {Anup Kumar}",

year = "2012",

month = may,

day = "1",

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language = "English",

volume = "352",

pages = "18--22",

journal = "Carbohydrate Research",

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Synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59 : Unexpected stereo outcome in glycosylation. / Sau, Abhijit; Panchadhayee, Rajib; Ghosh, Debjani; Misra, Anup Kumar.

In: Carbohydrate Research, Vol. 352, 01.05.2012, p. 18-22.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59

T2 - Unexpected stereo outcome in glycosylation

AU - Sau, Abhijit

AU - Panchadhayee, Rajib

AU - Ghosh, Debjani

AU - Misra, Anup Kumar

PY - 2012/5/1

Y1 - 2012/5/1

N2 - Convergent synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59 is presented. A thioglycoside disaccharide donor was prepared by the glycosylation of two thioglycosides by tuning their relative reactivity. An unexpected stereochemical outcome was observed in a glycosylation using an ethyl 2-O-acetyl-3-O-benzyl-4, 6-O-bensylidene-thio-galactoside donor, where the alpha-galactoside was formed in spite of the presence of the 2-O-acetyl participating group.

AB - Convergent synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59 is presented. A thioglycoside disaccharide donor was prepared by the glycosylation of two thioglycosides by tuning their relative reactivity. An unexpected stereochemical outcome was observed in a glycosylation using an ethyl 2-O-acetyl-3-O-benzyl-4, 6-O-bensylidene-thio-galactoside donor, where the alpha-galactoside was formed in spite of the presence of the 2-O-acetyl participating group.

KW - Glycosylation

KW - O-Polysaccharide

KW - Salmonella enterica

KW - Stereoselectivity

KW - Tetrasaccharide

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