Literature DB >> 19043616

An armed-disarmed approach for blocking aglycon transfer of thioglycosides.

Zhitao Li1, Jeffrey C Gildersleeve.   

Abstract

Thioglycosides are used frequently as glycosyl donors and as mimetics of O-glycosides. While being very useful, thioglycosides are prone to a detrimental side reaction referred to as aglycon transfer. In this paper, it is shown that aglycon transfer can be blocked by matching thioglycoside-containing acceptors with more armed glycosyl donors.

Entities:  

Year:  2007        PMID： 19043616      PMCID： PMC2587334          DOI： 10.1016/j.tetlet.2006.11.126

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  23 in total

1.  Simple and Efficient Method for the Oxidation of Sulfides to Sulfoxides: Application to the Preparation of Glycosyl Sulfoxides.

Authors:  Ramesh Kakarla; Richard G. Dulina; Nicole T. Hatzenbuhler; Y. W. Hui; Michael J. Sofia
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

2.  A convenient preparation of glycosyl chlorides from aryl/alkyl thioglycosides.

Authors:  S Sugiyama; J M Diakur
Journal:  Org Lett       Date:  2000-08-24       Impact factor: 6.005

3.  Intermolecular aglycon transfer of a phenyl 1-thiogalactosaminide derivative under trichloroacetimidate glycosylation conditions.

Authors:  F Belot; J C Jacquinet
Journal:  Carbohydr Res       Date:  1996-08-26       Impact factor: 2.104

4.  Mechanistic studies and methods to prevent aglycon transfer of thioglycosides.

Authors:  Zhitao Li; Jeffrey C Gildersleeve
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

5.  Carbohydrate array analysis of anti-Tn antibodies and lectins reveals unexpected specificities: implications for diagnostic and vaccine development.

Authors:  Joseph C Manimala; Zhitao Li; Amit Jain; Sharanjeet VedBrat; Jeffrey C Gildersleeve
Journal:  Chembiochem       Date:  2005-12       Impact factor: 3.164

Review 6.  Thio sugars: biological relevance as potential new therapeutics.

Authors:  Z J Witczak
Journal:  Curr Med Chem       Date:  1999-02       Impact factor: 4.530

7.  A glycosylation protocol based on activation of glycosyl 2-pyridyl sulfones with samarium triflate.

Authors:  G X Chang; T L Lowary
Journal:  Org Lett       Date:  2000-06-01       Impact factor: 6.005

Review 8.  Synthetic routes to thiooligosaccharides and thioglycopeptides.

Authors:  Kandasamy Pachamuthu; Richard R Schmidt
Journal:  Chem Rev       Date:  2006-01       Impact factor: 60.622

9.  Study of glycosylation with N-trichloroacetyl-D-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues.

Authors:  A A Sherman; O N Yudina; Y V Mironov; E V Sukhova; A S Shashkov; V M Menshov; N E Nifantiev
Journal:  Carbohydr Res       Date:  2001-11-01       Impact factor: 2.104

10.  Oligosaccharide structures of human colonic mucin.

Authors:  D K Podolsky
Journal:  J Biol Chem       Date:  1985-07-15       Impact factor: 5.157
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  3 in total

1.  Studies on the selectivity between nickel-catalyzed 1,2-cis-2-amino glycosylation of hydroxyl groups of thioglycoside acceptors with C2-substituted benzylidene N-phenyl trifluoroacetimidates and intermolecular aglycon transfer of the sulfide group.

Authors:  Fei Yu; Hien M Nguyen
Journal:  J Org Chem       Date:  2012-08-09       Impact factor: 4.354

2.  Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids.

Authors:  Peter J Jervis; Liam R Cox; Gurdyal S Besra
Journal:  J Org Chem       Date:  2010-12-14       Impact factor: 4.354

Review 3.  Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly.

Authors:  Weizhun Yang; Bo Yang; Sherif Ramadan; Xuefei Huang
Journal:  Beilstein J Org Chem       Date:  2017-10-09       Impact factor: 2.883
  3 in total

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