α-glycosphingolipids via chelation-induced anomerization of O- And s-glucuronic and galacturonic acid derivatives

Wayne Pilgrim; Paul V. Murphy

doi:10.1021/ol802915h

α-glycosphingolipids via chelation-induced anomerization of O- And s-glucuronic and galacturonic acid derivatives

Wayne Pilgrim, Paul V. Murphy

Infectious Disease

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

43 Citations (Scopus)

Abstract

Bacterial glycolipids containing either α-glucuronic acid or α-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel α-SO₂ glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of α) were observed from O-glycoside precursors.

Original language	English
Pages (from-to)	939-942
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	4
DOIs	https://doi.org/10.1021/ol802915h
Publication status	Published - 19 Feb 2009

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10.1021/ol802915h

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title = "α-glycosphingolipids via chelation-induced anomerization of O- And s-glucuronic and galacturonic acid derivatives",

abstract = "Bacterial glycolipids containing either α-glucuronic acid or α-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel α-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of α) were observed from O-glycoside precursors.",

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AU - Pilgrim, Wayne

AU - Murphy, Paul V.

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Y1 - 2009/2/19

N2 - Bacterial glycolipids containing either α-glucuronic acid or α-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel α-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of α) were observed from O-glycoside precursors.

AB - Bacterial glycolipids containing either α-glucuronic acid or α-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel α-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of α) were observed from O-glycoside precursors.

UR - https://www.scopus.com/pages/publications/62749183713

U2 - 10.1021/ol802915h

DO - 10.1021/ol802915h

M3 - Article

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JO - Organic Letters

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IS - 4

ER -

α-glycosphingolipids via chelation-induced anomerization of O- And s-glucuronic and galacturonic acid derivatives

Abstract

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