Literature DB >> 21663897

Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

Sophon Kaeothip1, Alexei V Demchenko.   

Abstract

Traditional strategies for oligosaccharide synthesis often require extensive protecting and/or leaving group manipulations between each glycosylation step, thereby increasing the total number of synthetic steps while decreasing the efficiency of the synthesis. In contrast, expeditious strategies allow for the rapid chemical synthesis of complex carbohydrates by minimizing extraneous chemical manipulations. Oligosaccharide synthesis by selective activation of one leaving group over another is one such expeditious strategy. Herein, the significant improvements that have recently emerged in the area of the selective activation are discussed. The development of orthogonal strategy further expands the scope of the selective activation methodology. Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID: 21663897      PMCID: PMC3129461          DOI: 10.1016/j.carres.2011.05.004

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  63 in total

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Journal:  Carbohydr Res       Date:  2000-05-05       Impact factor: 2.104

2.  Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method.

Authors:  H M Kim; I J Kim; S J Danishefsky
Journal:  J Am Chem Soc       Date:  2001-01-10       Impact factor: 15.419

3.  Synthesis of a library of fucopyranosyl-galactopyranosides consisting of a complete set of anomeric configurations and linkage positions.

Authors:  Isao Ohtsuka; Takuro Ako; Rumiko Kato; Shusaku Daikoku; Satomi Koroghi; Takuya Kanemitsu; Osamu Kanie
Journal:  Carbohydr Res       Date:  2006-04-27       Impact factor: 2.104

4.  An efficient, unambiguous synthesis of methyl 3-O-beta-D-galactopyranosyl-beta-D-galactopyranoside. Further studies on the specificity of antigalactopyranan monoclonal antibodies.

Authors:  P Kovác; C P Glaudemans; R B Taylor
Journal:  Carbohydr Res       Date:  1985-10-01       Impact factor: 2.104

Review 5.  Ionic liquids in oligosaccharide synthesis: towards mucin-type glycan probes.

Authors:  M Carmen Galan; Anthony P Corfield
Journal:  Biochem Soc Trans       Date:  2010-10       Impact factor: 5.407

6.  New principles for glycoside-bond formation.

Authors:  Xiangming Zhu; Richard R Schmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Oligomannan synthesis using ionic liquid supported glycosylation.

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Journal:  Org Lett       Date:  2007-12-11       Impact factor: 6.005

8.  Synthesis of the methyl and 1-octyl glycosides of the P-antigen tetrasaccharide (globotetraose).

Authors:  K Leontein; M Nilsson; T Norberg
Journal:  Carbohydr Res       Date:  1985-12-01       Impact factor: 2.104

9.  Synthesis of oligosaccharides corresponding to Vibrio cholerae O139 polysaccharide structures containing dideoxy sugars and a cyclic phosphate.

Authors:  Dominika Turek; Andreas Sundgren; Martina Lahmann; Stefan Oscarson
Journal:  Org Biomol Chem       Date:  2006-02-02       Impact factor: 3.876

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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  17 in total

Review 1.  Glycosyltransferase engineering for carbohydrate synthesis.

Authors:  John B McArthur; Xi Chen
Journal:  Biochem Soc Trans       Date:  2016-02       Impact factor: 5.407

Review 2.  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

3.  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

4.  Superarming of glycosyl donors by combined neighboring and conformational effects.

Authors:  Mads Heuckendorff; Hemali D Premathilake; Papapida Pornsuriyasak; Anders Ø Madsen; Christian M Pedersen; Mikael Bols; Alexei V Demchenko
Journal:  Org Lett       Date:  2013-09-05       Impact factor: 6.005

5.  On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: application to oligosaccharide assembly.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  J Org Chem       Date:  2011-08-17       Impact factor: 4.354

6.  Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis.

Authors:  S J Hasty; A V Demchenko
Journal:  Chem Heterocycl Compd (N Y)       Date:  2012-04       Impact factor: 1.277

7.  Assembly of a Complex Branched Oligosaccharide by Combining Fluorous-Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions.

Authors:  Wei Huang; Qi Gao; Geert-Jan Boons
Journal:  Chemistry       Date:  2015-08-06       Impact factor: 5.236

8.  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

9.  A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.

Authors:  Scott A Geringer; Yashapal Singh; Daniel J Hoard; Alexei V Demchenko
Journal:  Chemistry       Date:  2020-06-02       Impact factor: 5.236

10.  Realizing the Promise of Chemical Glycobiology.

Authors:  Lai-Xi Wang; Benjamin G Davis
Journal:  Chem Sci       Date:  2013-09-01       Impact factor: 9.825

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