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Sortase-Catalyzed Peptide−Glycosylphosphatidylinositol Analogue Ligation

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Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202
[email protected]
Cite this: J. Am. Chem. Soc. 2009, 131, 29, 9878–9879
Publication Date (Web):July 7, 2009
https://doi.org/10.1021/ja903231v
Copyright © 2009 American Chemical Society
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    Abstract

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    It is demonstrated that sortase A (SrtA) can catalyze efficient coupling of peptides to GPI analogues with a glycine residue attached to the phosphoethanolamine moiety at the nonreducing end to form GPI-linked peptides. This represents the first chemoenzymatic synthesis of GPI−peptide conjugates and is a proof-of-concept for the potential application of SrtA to the synthesis of more complex GPI-anchored peptides/glycopeptides and GPI-anchored proteins/glycoproteins.

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    Preparation of SrtA, 2, 3, 5, and 7; enzymatic reaction conditions and procedures; HPLC results for the reactions; and MS and NMR spectra of SrtA and 2−8. This material is available free of charge via the Internet at http://pubs.acs.org.

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