| A mechanistic study of sialic acid mutarotation: Implications for mutarotase enzymes. | |
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MedLine Citation:
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PMID: 21584336 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The mutarotation of N-acetylneuraminic acid (Neu5Ac) proceeds by four kinetically distinct pathways: (i) the acid-catalyzed reaction of neutral Neu5Ac; (ii) the spontaneous reaction of the carboxylic acid (the kinetically equivalent acid-catalyzed reaction on the anion being ruled out by the solvent deuterium kinetic isotope effect of 3.74 ± 0.68); (iii) a spontaneous, water-catalyzed, reaction of the anion; and (iv) a specific-base catalyzed reaction of the anion. The magnitude of the solvent kinetic isotope effect, k(H2O)/k(D2O) = 4.48 ± 0.74 is consistent with a ring-opening transition state in which a water molecule is deprotonating the anomeric hydroxyl group in concert with strengthening solvation of the ring oxygen atom. The mechanistic implications for Neu5Ac mutarotases are discussed. |
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Authors:
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Jefferson Chan; Gurtej Sandhu; Andrew J Bennet |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-5-17 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: - ISSN: 1477-0539 ISO Abbreviation: - Publication Date: 2011 May |
Date Detail:
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Created Date: 2011-5-17 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, V5A 1S6, British Columbia, Canada. bennet@sfu.ca. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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