Oxidation of peptides by methyl(trifluoromethyl)dioxirane: the protecting group matters.
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.
Rella
Maria Rosaria
MR
Department of Chemistry, Brown University, Providence, Rhode Island 02912, USA.
Williard
Paul G
PG
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*
D004952:Esters; D010455:Peptides; C445840:methyl(trifluoromethyl)dioxirane; D005027:Ethylene Oxide