| Metabolism of diazirine-modified N-acetylmannosamine analogs to photocrosslinking sialosides. | |
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MedLine Citation:
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PMID: 21838313 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Terminal sialic acid residues often mediate the interactions of cell surface glycoconjugates. Sialic acid-dependent interactions typically exhibit rapid dissociation rates, precluding the use of traditional biological techniques for complex isolation. To stabilize these transient interactions, we employ a targeted photocrosslinking approach in which the diazirine photocrosslinker is incorporated into cell surface sialylated glycoconjugates through the use of metabolic oligosaccharide engineering. We report that three diazirine-modified N-acetylmannosamine (ManNAc) analogs of different sizes were each metabolized to their respective sialic acid analogs, which were added to both glycoproteins and glycolipids. Diazirine-modified sialic acid analogs could be incorporated into both α2-3 and α2-6 linkages. Upon exposure to UV irradiation, diazirine-modified glycoconjugates were covalently crosslinked to their interaction partners. We demonstrate that all three diazirine-modified analogs were capable of competing with endogeneous sialic acid, albeit to varying degrees. We found that larger analogs were less efficiently metabolized, yet could still function as effective crosslinkers. Notably, the addition of the diazirine substituent interferes with metabolism of ManNAc analogs to glycans other than sialosides, providing fidelity to selectively incorporate the crosslinker into sialylated molecules. These compounds are non-toxic and display only minimal growth inhibition at the concentrations required for crosslinking studies. This report provides essential information for the deployment of photocrosslinking analogs to capture and study ephemeral, yet essential, sialic acid-mediated interactions. |
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Authors:
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Michelle R Bond; Haochi Zhang; Jaekuk Kim; Seok-Ho Yu; Fan Yang; Steven M Patrie; Jennifer J Kohler |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-8-15 |
Journal Detail:
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Title: Bioconjugate chemistry Volume: - ISSN: 1520-4812 ISO Abbreviation: - Publication Date: 2011 Aug |
Date Detail:
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Created Date: 2011-8-15 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9010319 Medline TA: Bioconjug Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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