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Chemical Pyrophosphorylation of Functionally Diverse Peptides

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posted on 2014-01-08, 00:00 authored by Alan M. Marmelstein, Lisa M. Yates, John H. Conway, Dorothea Fiedler
A highly selective and convenient method for the synthesis of pyro­phospho­peptides in solution is reported. The remarkable compatibility with functional groups (alcohol, thiol, amine, carboxylic acid) in the peptide substrates suggests that the intrinsic nucleophilicity of the phosphoserine residue is much higher than previously appreciated. Because the methodology operates in polar solvents, including water, a broad range of pyro­phospho­peptides can be accessed. We envision these peptides will find widespread applications in the development of mass spectrometry and antibody-based detection methods for pyro­phospho­proteins.

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