Literature DB >> 18798644

Two-step synthesis of the immunogenic bacterial glycolipid BbGL1.

Suvarn S Kulkarni1, Jacquelyn Gervay-Hague.   

Abstract

Chemical synthesis of a bacterial glycolipid BbGL1 is reported in two steps starting from per-O-TMS D-galactose. The key features are glycosyl iodide mediated beta-stereoselective glycosylation in the absence of neighboring group participation and regioselective acylation.

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Year:  2008        PMID： 18798644      PMCID： PMC4492534          DOI： 10.1021/ol801780c

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


  14 in total

1.  Synthesis of an experimental glycolipoprotein vaccine against Lyme disease.

Authors:  Vince Pozsgay; Joanna Kubler-Kielb
Journal:  Carbohydr Res       Date:  2006-11-17       Impact factor: 2.104

2.  Highly beta-selective O-glucosidation due to the restricted twist-boat conformation.

Authors:  Yasunori Okada; Tatsuya Mukae; Kotaro Okajima; Miyoko Taira; Mari Fujita; Hidetoshi Yamada
Journal:  Org Lett       Date:  2007-03-15       Impact factor: 6.005

3.  Efficient syntheses of beta-cyanosugars using glycosyl iodides derived from per-O-silylated mono- and disaccharides.

Authors:  A S Bhat; J Gervay-Hague
Journal:  Org Lett       Date:  2001-06-28       Impact factor: 6.005

4.  Solution- and solid-phase oligosaccharide synthesis using glucosyl iodides: a comparative study.

Authors:  Son N Lam; Jacquelyn Gervay-Hague
Journal:  Carbohydr Res       Date:  2002-11-19       Impact factor: 2.104

5.  Efficient synthesis of a C-analogue of the immunogenic bacterial glycolipid BbGL2.

Authors:  Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

6.  Solution-phase hexasaccharide synthesis using glucosyl iodides.

Authors:  Son N Lam; Jacquelyn Gervay-Hague
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

7.  Efficient synthesis of alpha-galactosyl ceramide analogues using glycosyl iodide donors.

Authors:  Wenjun Du; Jacquelyn Gervay-Hague
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

8.  Acylated cholesteryl galactoside as a novel immunogenic motif in Borrelia burgdorferi sensu stricto.

Authors:  Nicolas W J Schröder; Ursula Schombel; Holger Heine; Ulf B Göbel; Ulrich Zähringer; Ralf R Schumann
Journal:  J Biol Chem       Date:  2003-06-16       Impact factor: 5.157

9.  A newly discovered cholesteryl galactoside from Borrelia burgdorferi.

Authors:  Gil Ben-Menachem; Joanna Kubler-Kielb; Bruce Coxon; Alfred Yergey; Rachel Schneerson
Journal:  Proc Natl Acad Sci U S A       Date:  2003-06-10       Impact factor: 11.205

10.  Efficient, one-pot syntheses of biologically active alpha-linked glycolipids.

Authors:  Wenjun Du; Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  Chem Commun (Camb)       Date:  2007-06-21       Impact factor: 6.222
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  7 in total

1.  Two-step functionalization of oligosaccharides using glycosyl iodide and trimethylene oxide and its applications to multivalent glycoconjugates.

Authors:  Hsiao-Wu Hsieh; Ryan A Davis; Jessica A Hoch; Jacquelyn Gervay-Hague
Journal:  Chemistry       Date:  2014-04-08       Impact factor: 5.236

2.  Synthesis and structural characterization of three unique Helicobacter pylori α-cholesteryl phosphatidyl glucosides.

Authors:  Huy Q Nguyen; Ryan A Davis; Jacquelyn Gervay-Hague
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

3.  Synthesis of cholesteryl-α-D-lactoside via generation and trapping of a stable β-lactosyl iodide.

Authors:  Ryan A Davis; James C Fettinger; Jacquelyn Gervay-Hague
Journal:  Tetrahedron Lett       Date:  2015-05-08       Impact factor: 2.415

4.  Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-D-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori.

Authors:  Ryan A Davis; Chun-Hung Lin; Jacquelyn Gervay-Hague
Journal:  Chem Commun (Camb)       Date:  2012-08-02       Impact factor: 6.222

Review 5.  Silyl-protective groups influencing the reactivity and selectivity in glycosylations.

Authors:  Mikael Bols; Christian Marcus Pedersen
Journal:  Beilstein J Org Chem       Date:  2017-01-16       Impact factor: 2.883

6.  Integrating ReSET with glycosyl iodide glycosylation in step-economy syntheses of tumor-associated carbohydrate antigens and immunogenic glycolipids.

Authors:  Hsiao-Wu Hsieh; Matthew W Schombs; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2014-02-07       Impact factor: 4.354

7.  Tandem glycosyl iodide glycosylation and regioselective enzymatic acylation affords 6-O-tetradecanoyl-α-d-cholesterylglycosides.

Authors:  Ryan A Davis; James C Fettinger; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2014-08-13       Impact factor: 4.354
  7 in total

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