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.

SUBMITTER: Rella MR 

PROVIDER: S-EPMC3220948 | biostudies-literature | 2007 Jan

REPOSITORIES: biostudies-literature