NDLI: Metabolism of diazirine-modified N-acetylmannosamine analogs to photocrosslinking sialosides

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Metabolism of diazirine-modified N-acetylmannosamine analogs to photocrosslinking sialosides

Content Provider	PubMed Central
Author	Bond, Michelle R. Zhang, Haochi Kim, Jaekuk Yu, Seok-ho Yang, Fan Patrie, Steven M. Kohler, Jennifer J.
Abstract	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 a diazirine photocrosslinker is incorporated into cell surface sialylated glycoconjugates through the use of metabolic oligosaccharide engineering. We describe three diazirine-modified N-acetylmannosamine (ManNAc) analogs in which the length of the linker between the pyranose ring and the diazirine was varied. These analogs were each metabolized to their respective sialic acid counterparts, 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.
Related Links	http://dx.doi.org/10.1021/bc2002117
Ending Page	1823
Page Count	13
Starting Page	1811
File Format	PDF
ISSN	10431802
e-ISSN	15204812
Journal	Bioconjugate chemistry
Issue Number	9
Volume Number	22
Language	English
Publisher Date	2011-09-21
Access Restriction	Open
Subject Keyword	Biotechnology Organic Chemistry Bioengineering Pharmacology Pharmaceutical Science Biomedical Engineering Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Pharmacology Bioengineering Biomedical Engineering Biotechnology Pharmaceutical Science

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