title: Incorporation of phosphotyrosyl mimetic 4-(phosphonodifluoromethyl)phenylalanine (F2Pmp) into signal transduction-directed peptides.
abstract: Phosphotyrosyl (pTyr)-containing sequences in proteins serve important roles in cellular signal transduction. Often, synthetic pTyr-containing peptides based on cognate sequences surrounding these pTyr residues can exhibit pharmacologically useful properties of full phosphoproteins. However, such pTyr-containing peptides have limited use in whole-cell systems resulting from lability of the phosphate ester bond to protein-tyrosine phosphatases (PTPs). For this reason, a number of phosphatase-stable pTyr mimetics have been developed that retain certain of the chemical and pharmacological properties of pTyr itself. Among these, difluoro-phosphonomethyl phenylalanine (F2Pmp) has shown widespread utility in a variety of signal transduction settings, particularly those involving PTPs. This chapter provides practical techniques for the synthesis of a range of F2Pmp-containing peptides.
authors.affiliation: Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, MD, USA.
authors.forename: Zhu-Jun
authors.initials: ZJ
authors.lastname: Yao
authors.forename: Kyeong
authors.initials: K
authors.lastname: Lee
authors.forename: Terrence R
authors.initials: TR
authors.lastname: Burke
mesh_terms: D000595:Amino Acid Sequence; D066298:In Vitro Techniques; D008967:Molecular Biology / Q000379:methods*; D018716:Molecular Mimicry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D017027:Protein Tyrosine Phosphatases / Q000378:metabolism; D015398:Signal Transduction; D018909:src Homology Domains
chemical_list: D009842:Oligopeptides; C089985:phosphonodifluoromethylphenylalanine; D010649:Phenylalanine; D017027:Protein Tyrosine Phosphatases