title: Versatile Synthesis of Stable, Functional Polypeptides via Reaction with Epoxides.
abstract: Methodology was developed for efficient alkylation of methionine residues using epoxides as a general strategy to introduce a wide range of functional groups onto polypeptides. Use of a spacer between epoxide and functional groups further allowed addition of sterically demanding functionalities. Contrary to other methods to alkylate methionine residues, epoxide alkylations allow the reactions to be conducted in wet protic media and give sulfonium products that are stable against dealkylation. These functionalizations are notable since they are chemoselective, utilize stable and readily available epoxides, and allow facile incorporation of an unprecedented range of functional groups onto simple polypeptides using stable linkages.
authors.affiliation: †Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095-1569, United States.
authors.forename: Eric G
authors.initials: EG
authors.lastname: Gharakhanian
authors.affiliation: †Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, California 90095-1569, United States.|‡Department of Bioengineering, University of California Los Angeles, Los Angeles, California 90095-1600, United States.
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Deming
mesh_terms: D000478:Alkylation; D004852:Epoxy Compounds / Q000737:chemistry*; D008715:Methionine / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004852:Epoxy Compounds; D010455:Peptides; D008715:Methionine