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Chemoenzymatic Synthesis of O-Mannosylpeptides in Solution and on Solid Phase
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2012 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 134, no 10, 4521-4524 p.Article in journal (Refereed) Published
Abstract [en]

O-Mannosyl glycans are known to play an important role in regulating the function of alpha-dystroglycan (alpha-DG), as defective glycosylation is associated with various phenotypes of congenital muscular dystrophy. Despite the well-established biological significance of these glycans, questions regarding their precise molecular function remain unanswered. Further biological investigation will require synthetic methods for the generation of pure samples of homogeneous glycopeptides with diverse sequences. Here we describe the first total syntheses of glycopeptides containing the tetrasaccharide NeuNAc alpha 2-3Gal beta 1-4GlcNAc beta 1-2Man alpha, which is reported to be the most abundant O-mannosyl glycan on alpha-DG. Our approach is based on biomimetic stepwise assembly from the reducing end and also gives access to the naturally occurring mono-, di-, and trisaccharide substructures. In addition to the total synthesis, we have developed a one-pot enzymatic cascade leading to the rapid synthesis of the target tetrasaccharide. Finally, solid-phase synthesis of the desired glycopeptides directly on a gold microarray platform is described.

Place, publisher, year, edition, pages
2012. Vol. 134, no 10, 4521-4524 p.
National Category
Chemical Sciences
URN: urn:nbn:se:su:diva-76150DOI: 10.1021/ja211861mISI: 000301990600018OAI: diva2:525888
Knut and Alice Wallenberg FoundationSwedish Research Council
12Available from: 2012-05-09 Created: 2012-05-09 Last updated: 2012-07-13Bibliographically approved

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Fontana, CarolinaWidmalm, Göran
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Department of Organic Chemistry
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