Fluorine in Peptides: The Synthesis of alpha-Fluoro-beta-Amino Dipeptides by Direct Deoxofluorination/Rearrangement of N-Seryl Dipeptides

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

This article describes the stereo- and regioselectivity of the deoxofluorination of N-terminal dipeptides bearing a serine residue to generate, after rearrangement, a-fluoro-beta-amine-terminated dipeptides. The ratio of the rearranged a-fluorinated regioisomer is increased, relative to the non-rearranged beta-fluoro isomer, with N-alkylated amides. Otherwise, an intramolecular H-bond between the free amine and the amide NH suppresses formation of the key aziridinium intermediate required for a-fluorination. N-Methyl and N-allyl amides give exclusively a-fluorination products. Subsequent deprotection of the N-allyl amide to give a a-fluoro-beta-amino dipeptide product is demonstrated.

Original languageEnglish
Pages (from-to)2331-2347
Number of pages17
JournalHelvetica Chimica Acta
Volume95
Issue number12
DOIs
Publication statusPublished - Dec 2012

Fingerprint

Dive into the research topics of 'Fluorine in Peptides: The Synthesis of alpha-Fluoro-beta-Amino Dipeptides by Direct Deoxofluorination/Rearrangement of N-Seryl Dipeptides'. Together they form a unique fingerprint.

Cite this