Literature DB >> 19178158

Alpha-glycosphingolipids via chelation-induced anomerization of O- and S-glucuronic and galacturonic acid derivatives.

Wayne Pilgrim1, Paul V Murphy.   

Abstract

Bacterial glycolipids containing either alpha-glucuronic acid or alpha-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 alpha-SO(2) glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.

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Year:  2009        PMID: 19178158     DOI: 10.1021/ol802915h

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Ieodoglucomide C and Ieodoglycolipid, New Glycolipids from a Marine-Derived Bacterium Bacillus licheniformis 09IDYM23.

Authors:  Fakir Shahidullah Tareq; Hyi-Seung Lee; Yeon-Ju Lee; Jong Seok Lee; Hee Jae Shin
Journal:  Lipids       Date:  2015-04-18       Impact factor: 1.880

2.  Impact of sugar stereochemistry on natural killer T cell stimulation by bacterial glycolipids.

Authors:  Shenglou Deng; Jochen Mattner; Zhuo Zang; Li Bai; Luc Teyton; Albert Bendelac; Paul B Savage
Journal:  Org Biomol Chem       Date:  2011-09-16       Impact factor: 3.876

3.  Divergent Synthesis of Chondroitin Sulfate Disaccharides and Identification of Sulfate Motifs that Inhibit Triple Negative Breast Cancer.

Authors:  Zhong Wei Poh; Chin Heng Gan; Eric J Lee; Suxian Guo; George W Yip; Yulin Lam
Journal:  Sci Rep       Date:  2015-09-24       Impact factor: 4.379

Review 4.  The Therapeutic Potential of Migrastatin-Core Analogs for the Treatment of Metastatic Cancer.

Authors:  Ernest Giralt; Daniele Lo Re
Journal:  Molecules       Date:  2017-02-09       Impact factor: 4.411

5.  Mycothiol synthesis by an anomerization reaction through endocyclic cleavage.

Authors:  Shino Manabe; Yukishige Ito
Journal:  Beilstein J Org Chem       Date:  2016-02-22       Impact factor: 2.883

6.  Synthesis of α-O- and α-S-glycosphingolipids related to Sphingomonous cell wall antigens using anomerisation.

Authors:  Wayne Pilgrim; Ciaran O'Reilly; Paul V Murphy
Journal:  Molecules       Date:  2013-09-12       Impact factor: 4.411

  6 in total

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