title: Oxidation of peptides by methyl(trifluoromethyl)dioxirane: the protecting group matters.
abstract: Representative Boc-protected and acetyl-protected peptide methyl esters bearing alkyl side chains undergo effective oxidation using methyl(trifluoromethyl)dioxirane (1b) under mild conditions. We observe a protecting group dependency in the chemoselectivity displayed by the dioxirane 1b. N-Hydroxylation occurs in the case of the Boc-protected peptides, and side chain hydroxylation takes place in the case of acetyl-protected peptides. Both are attractive transformations since they yield derivatized peptides that serve as valuable synthons.
authors.affiliation: Department of Chemistry, Brown University, Providence, Rhode Island 02912, USA.
authors.forename: Maria Rosaria
authors.initials: MR
authors.lastname: Rella
authors.forename: Paul G
authors.initials: PG
authors.lastname: Williard
mesh_terms: D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D005027:Ethylene Oxide / Q000031:analogs & derivatives* / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*
chemical_list: D004952:Esters; D010455:Peptides; C445840:methyl(trifluoromethyl)dioxirane; D005027:Ethylene Oxide