title: Chemical pyrophosphorylation of functionally diverse peptides.
abstract: 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.
authors.affiliation: Department of Chemistry, Princeton University , Washington Road, Princeton, New Jersey 08544, United States.
authors.forename: Alan M
authors.initials: AM
authors.lastname: Marmelstein
authors.forename: Lisa M
authors.initials: LM
authors.lastname: Yates
authors.forename: John H
authors.initials: JH
authors.lastname: Conway
authors.forename: Dorothea
authors.initials: D
authors.lastname: Fiedler
mesh_terms: D007295:Inositol Phosphates / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry / Q000378:metabolism*; D010766:Phosphorylation
chemical_list: D007295:Inositol Phosphates; D010455:Peptides