ORGN 919 |
| Representative small 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 give easy access to valuable synthons in hydroxamate and polypeptide preparations and can be used in the development of peptide derivatives of biological relevance. |
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Proteins, Peptides, Amino Acids, and Enzyme Inhibitors
8:00 AM-12:00 PM, Thursday, August 23, 2007 BCEC -- 258B, Oral
Division of Organic Chemistry |