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Literature DB >> 18452900

C-5 modifications in N-acetyl-neuraminic acid: scope and limitations.

Abstract

Glycoconjugates containing sialic acid are involved in a large variety of biological phenomena, including cell-cell adhesion, recognition by viruses and bacteria, and oncogenesis. Therefore, they are important synthetic targets for the design of drugs and vaccines. In the last decades, different methodologies that improve yield and stereoselectivity in sialylation reactions have been investigated. This review summarizes the latest developments in the synthesis of C-5 modified sialic acid glycosyl donors and glycosyl acceptors and their application in the synthesis of alpha-sialosides.

Entities: Chemical Gene

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Year: 2008 PMID： 18452900 DOI： 10.1016/j.carres.2008.04.007

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

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Cited

20 in total

1. Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Authors: Asiri A Hettikankanamalage; Robert Lassfolk; Filip S Ekholm; Reko Leino; David Crich
Journal: Chem Rev Date: 2020-07-05 Impact factor: 60.622

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

Authors: Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal: Chem Rev Date: 2018-05-30 Impact factor: 60.622

3. Synthesis and immunological study of α-2,9-oligosialic acid conjugates as anti-group C meningitis vaccines.

Authors: Guochao Liao; Zhifang Zhou; Zhongwu Guo
Journal: Chem Commun (Camb) Date: 2015-06-14 Impact factor: 6.222

4. Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series.

Authors: Indrajeet Sharma; Luis Bohé; David Crich
Journal: Carbohydr Res Date: 2012-06-07 Impact factor: 2.104

5. Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors: David Crich
Journal: J Org Chem Date: 2011-10-04 Impact factor: 4.354

6. The isothiocyanato moiety: an ideal protecting group for the stereoselective synthesis of sialic acid glycosides and subsequent diversification.

Authors: Appi Reddy Mandhapati; Salla Rajender; Jonathan Shaw; David Crich
Journal: Angew Chem Int Ed Engl Date: 2014-11-28 Impact factor: 15.336

C-5 modifications in N-acetyl-neuraminic acid: scope and limitations.

1. Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

3. Synthesis and immunological study of α-2,9-oligosialic acid conjugates as anti-group C meningitis vaccines.

4. Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series.

5. Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

6. The isothiocyanato moiety: an ideal protecting group for the stereoselective synthesis of sialic acid glycosides and subsequent diversification.

7. Total synthesis of trifluorobutyryl-modified, globally protected sialyl Lewis x by a convergent [2+2] approach.

8. Facile and robust methods for the regioselective acylation of N-acetylneuraminic acid.

9. Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides.

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

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.