Literature DB >> 25328276

In situ preactivation strategies for the expeditious synthesis of oligosaccharides: A review.

Samantha K Bouhall1, Steven J Sucheck1.   

Abstract

Carbohydrates have gained increasing appreciation over the last few decades for their fundamental roles in all essential areas of life. As a result, there has been a surge of activity in synthetic glycosylation strategies to construct useful oligosaccharides. This review evaluates the advances in synthetic carbohydrate chemistry, specifically preactivation methodologies, stereoselective β-mannosylations, and an automated, electrochemical preactivation method. Also discussed is the use of preactivation as a tool to study reactive intermediates, and applications of preactivation protocols in the one pot-synthesis of a hyaluronic acid decasaccharide and one-pot synthesis of a tristearoyl lipomannan containing a pseudotrisaccharide.

Entities:  

Year:  2014        PMID: 25328276      PMCID: PMC4196384          DOI: 10.1080/07328303.2014.931964

Source DB:  PubMed          Journal:  J Carbohydr Chem        ISSN: 0732-8303            Impact factor:   1.667


  34 in total

Review 1.  Targeting glycosylation as a therapeutic approach.

Authors:  Raymond A Dwek; Terry D Butters; Frances M Platt; Nicole Zitzmann
Journal:  Nat Rev Drug Discov       Date:  2002-01       Impact factor: 84.694

2.  A supramolecular peptide synthesizer.

Authors:  Jordi Bertran-Vicente; Christian P R Hackenberger
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-17       Impact factor: 15.336

3.  ortho-Methylphenylthioglycosides as glycosyl building blocks for preactivation-based oligosaccharide synthesis.

Authors:  Peng Peng; De-Cai Xiong; Xin-Shan Ye
Journal:  Carbohydr Res       Date:  2013-11-22       Impact factor: 2.104

4.  A new, iterative strategy of oligosaccharide synthesis based on highly reactive beta-bromoglycosides derived from selenoglycosides.

Authors:  S Yamago; T Yamada; O Hara; H Ito; Y Mino; J I Yoshida
Journal:  Org Lett       Date:  2001-11-29       Impact factor: 6.005

5.  Chemistry of 4,6-O-Benzylidene-D-glycopyranosyl Triflates: Contrasting Behavior between the Gluco and Manno Series.

Authors:  David Crich; Weiling Cai
Journal:  J Org Chem       Date:  1999-06-25       Impact factor: 4.354

6.  Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.

Authors:  Jeroen D C Codée; Remy E J N Litjens; René den Heeten; Herman S Overkleeft; Jacques H van Boom; Gijs A van der Marel
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

7.  Pre-activation-based one-pot synthesis of an alpha-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide.

Authors:  Bin Sun; Balasubramanian Srinivasan; Xuefei Huang
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

8.  Automated carbohydrate synthesis as platform to address fundamental aspects of glycobiology--current status and future challenges.

Authors:  Peter H Seeberger
Journal:  Carbohydr Res       Date:  2008-05-29       Impact factor: 2.104

9.  Synthesis of a tristearoyl lipomannan via preactivation-based iterative one-pot glycosylation.

Authors:  Jian Gao; Zhongwu Guo
Journal:  J Org Chem       Date:  2013-12-03       Impact factor: 4.354

10.  IPy2BF4-mediated transformation of n-pentenyl glycosides to glycosyl fluorides: a new pair of semiorthogonal glycosyl donors.

Authors:  J Cristóbal López; Clara Uriel; Alejandra Guillamón-Martín; Serafín Valverde; Ana M Gómez
Journal:  Org Lett       Date:  2007-06-20       Impact factor: 6.005

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  7 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active-Latent, Armed-Disarmed, Selective, and Orthogonal Activations.

Authors:  Scott J Hasty; Mithila D Bandara; Nigam P Rath; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-02-07       Impact factor: 4.354

3.  Regenerative Glycosylation.

Authors:  Yashapal Singh; Tinghua Wang; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-12-22       Impact factor: 4.354

Review 4.  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

Review 5.  Intramolecular glycosylation.

Authors:  Xiao G Jia; Alexei V Demchenko
Journal:  Beilstein J Org Chem       Date:  2017-09-29       Impact factor: 2.883

Review 6.  Recent Progress in Chemo-Enzymatic Methods for the Synthesis of N-Glycans.

Authors:  Qiang Chao; Yi Ding; Zheng-Hui Chen; Meng-Hai Xiang; Ning Wang; Xiao-Dong Gao
Journal:  Front Chem       Date:  2020-06-16       Impact factor: 5.221

7.  Oligosaccharide synthesis on soluble high-molecular weight pHEMA using a photo-cleavable linker.

Authors:  Abhishek Vartak; Sandeep Thanna; Kyle Meyer; Miranda Dermanelian; Steven J Sucheck
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 4.036

  7 in total

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