Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology

[Image: see text] Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-...

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Autores principales: Park, Simon S., Gervay-Hague, Jacquelyn
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184446/
https://www.ncbi.nlm.nih.gov/pubmed/25247390
http://dx.doi.org/10.1021/ol502389g
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author Park, Simon S.
Gervay-Hague, Jacquelyn
author_facet Park, Simon S.
Gervay-Hague, Jacquelyn
author_sort Park, Simon S.
collection PubMed
description [Image: see text] Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-silylated Neu5Ac ester with AcOH and Ac(2)O in pyridine promotes regioselective silyl ether/acetate exchange in the following order: C(4) (2°) > C(9) (1°) > C(8) (2°) > C(2) (anomeric). Subsequent hydrogenolysis affords the corresponding sialic acid analogues as useful chemical biology tools.
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spelling pubmed-41844462015-09-23 Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology Park, Simon S. Gervay-Hague, Jacquelyn Org Lett [Image: see text] Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-silylated Neu5Ac ester with AcOH and Ac(2)O in pyridine promotes regioselective silyl ether/acetate exchange in the following order: C(4) (2°) > C(9) (1°) > C(8) (2°) > C(2) (anomeric). Subsequent hydrogenolysis affords the corresponding sialic acid analogues as useful chemical biology tools. American Chemical Society 2014-09-23 2014-10-03 /pmc/articles/PMC4184446/ /pubmed/25247390 http://dx.doi.org/10.1021/ol502389g Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Park, Simon S.
Gervay-Hague, Jacquelyn
Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology
title Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology
title_full Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology
title_fullStr Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology
title_full_unstemmed Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology
title_short Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology
title_sort synthesis of partially o-acetylated n-acetylneuraminic acid using regioselective silyl exchange technology
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184446/
https://www.ncbi.nlm.nih.gov/pubmed/25247390
http://dx.doi.org/10.1021/ol502389g
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