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Deacetylation of N-alpha-methylated glycopeptides reveals that aza-enolates provide protection against beta-elimination of carbohydrates O-linked to serine
Umeå University, Faculty of Science and Technology, Chemistry.
Umeå University, Faculty of Science and Technology, Chemistry.
2000 (English)In: Tetrahedron Letters, Vol. 41, 4435-9 p.Article in journal (Refereed) Published
Abstract [en]

Three glycopeptides Ac-Ala-Ser[beta-Gal(OAc)(4)]-Phe-NH2, Ac-Ala-N-alpha-Me-Ser[beta-Gal(OAc)(4)]-Phe-NH2 and Ac-Ala-Ser[beta-Gal(OAc)(4)]-N-alpha-Me-Phe-NH2 have been prepared and treated with base in order to remove the O-acetyl protective groups. The glycopeptide which carried the N-methyl group on the glycosylated serine, was substantially more susceptible to beta-elimination than the two others. This reveals that formation of an aza-enolate from the amide bond to a glycosylated serine provides protection against p-elimination under basic conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

Place, publisher, year, edition, pages
2000. Vol. 41, 4435-9 p.
Identifiers
URN: urn:nbn:se:umu:diva-8452DOI: doi:10.1016/S0040-4039(00)00611-0OAI: oai:DiVA.org:umu-8452DiVA: diva2:148123
Available from: 2008-01-24 Created: 2008-01-24 Last updated: 2011-01-14Bibliographically approved

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