Literature DB >> 16305537

Recent advances in the synthesis of C-oligosaccharides.

Xuejun Yuan1, Robert J Linhardt.   

Abstract

This paper reviews the recent advances in the synthesis of catabolically stable sugar mimetics, C-oligosaccharides. These compounds are synthetic analogs of the naturally occurring O-oligosaccharides, in which the interglycosidic oxygen has been replaced by a methylene group. This review is organized in terms of chemistry used to assemble C-oligosaccarides under the sub-headings: anionic approaches, cationic methods, reductive glycosyl samarium chemistry, cyclization methodology, and free radical chemistry.

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Year:  2005        PMID: 16305537      PMCID: PMC4121988          DOI: 10.2174/156802605774643033

Source DB:  PubMed          Journal:  Curr Top Med Chem        ISSN: 1568-0266            Impact factor:   3.295


  18 in total

1.  Reductive Samariation of Anomeric 2-Pyridyl Sulfones with Catalytic Nickel: An Unexpected Improvement in the Synthesis of 1,2-trans-Diequatorial C-Glycosyl Compounds.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-11-17       Impact factor: 15.336

2.  Sequencing Reactions with Samarium(II) Iodide.

Authors:  Gary A. Molander; Christina R. Harris
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

3.  Glycobiology: Toward Understanding the Function of Sugars.

Authors:  Raymond A. Dwek
Journal:  Chem Rev       Date:  1996-03-28       Impact factor: 60.622

4.  Synthesis of a C-glycoside analogue of sTn: an HIV- and tumor-associated antigen.

Authors:  Balagurunathan Kuberan; Sulthan A Sikkander; Hiroshi Tomiyama; Robert J Linhardt
Journal:  Angew Chem Int Ed Engl       Date:  2003-05-09       Impact factor: 15.336

Review 5.  Lectins as cell recognition molecules.

Authors:  N Sharon; H Lis
Journal:  Science       Date:  1989-10-13       Impact factor: 47.728

6.  Ramberg-Bäcklund Approaches to the Synthesis of C-Linked Disaccharides.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-10-04       Impact factor: 15.336

7.  An olefin metathesis route for the preparation of (1-->6)-linked C-disaccharide glycals. A convergent and flexible approach to C-saccharide synthesis.

Authors:  M H Postema; D Calimente; L Liu; T L Behrmann
Journal:  J Org Chem       Date:  2000-09-22       Impact factor: 4.354

8.  Synthesis of alpha- and beta-D-(1-->6)-C-Disaccharides by Wittig Olefination of Formyl C-Glycosides with Glycopyranose 6-Phosphoranes.

Authors:  Alessandro Dondoni; Helene M. Zuurmond; Alessia Boscarato
Journal:  J Org Chem       Date:  1997-11-14       Impact factor: 4.354

9.  Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide.

Authors:  Jason L McCartney; Christopher T Meta; Robert M Cicchillo; Matthew D Bernardina; Timothy R Wagner; Peter Norris
Journal:  J Org Chem       Date:  2003-12-26       Impact factor: 4.354

10.  Introducing a C-interglycosidic bond in a biologically active pentasaccharide hardly affects its biological properties.

Authors:  M Petitou; J P Hérault; J C Lormeau; A Helmboldt; J M Mallet; P Sinaÿ; J M Herbert
Journal:  Bioorg Med Chem       Date:  1998-09       Impact factor: 3.641

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  9 in total

1.  Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

Authors:  David Crich; Indrajeet Sharma
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Synthesis of nor-C-linked neuraminic acid disaccharide: a versatile precursor of C-analogs of oligosialic acids and gangliosides.

Authors:  Xuejun Yuan; Dino K Ress; Robert J Linhardt
Journal:  J Org Chem       Date:  2007-03-20       Impact factor: 4.354

3.  Cation Clock Reactions for the Determination of Relative Reaction Kinetics in Glycosylation Reactions: Applications to Gluco- and Mannopyranosyl Sulfoxide and Trichloroacetimidate Type Donors.

Authors:  Philip O Adero; Takayuki Furukawa; Min Huang; Debaraj Mukherjee; Pascal Retailleau; Luis Bohé; David Crich
Journal:  J Am Chem Soc       Date:  2015-08-07       Impact factor: 15.419

4.  C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.

Authors:  Ahmad S Altiti; David R Mootoo
Journal:  Carbohydr Res       Date:  2015-02-21       Impact factor: 2.104

5.  Chemoenzymatic synthesis of mono- and di-fluorinated Thomsen-Friedenreich (T) antigens and their sialylated derivatives.

Authors:  Jun Yan; Xi Chen; Fengshan Wang; Hongzhi Cao
Journal:  Org Biomol Chem       Date:  2012-12-14       Impact factor: 3.876

6.  Synthesis of C-glycoside analogues of beta-galactosamine-(1-->4)-3-O-methyl-D-chiro-inositol and assay as activator of protein phosphatases PDHP and PP2Calpha.

Authors:  Sunej K Hans; Fatoumata Camara; Ahmad Altiti; Alejandro Martín-Montalvo; David L Brautigan; Douglas Heimark; Joseph Larner; Scott Grindrod; Milton L Brown; David R Mootoo
Journal:  Bioorg Med Chem       Date:  2010-01-04       Impact factor: 3.641

7.  Synthesis and conformational behavior of the difluoromethylene linked C-glycoside analog of beta-galactopyranosyl-(1<-->1)-alpha-mannopyranoside.

Authors:  Richard W Denton; Kurissery A Tony; José Juan Hernández-Gay; F Javier Cañada; Jesús Jiménez-Barbero; David R Mootoo
Journal:  Carbohydr Res       Date:  2007-06-13       Impact factor: 2.104

8.  Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals.

Authors:  Henok H Kinfe; Fanuel M Mebrahtu; Mandlenkosi M Manana; Kagiso Madumo; Mokela S Sokamisa
Journal:  Beilstein J Org Chem       Date:  2015-04-29       Impact factor: 2.883

9.  Synthesis of C-Oligosaccharides through Versatile C(sp3 )-H Glycosylation of Glycosides.

Authors:  Jun Wu; Adelina Kopp; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2022-01-27       Impact factor: 16.823

  9 in total

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