Tt. Tran et al., FLUORINATED PEPTIDES INCORPORATING A 4-FLUOROPROLINE RESIDUE AS POTENTIAL INHIBITORS OF HIV PROTEASE, Journal of fluorine chemistry, 82(2), 1997, pp. 125-130
N-Fmoc-4-fluoro-L-proline methyl ester was prepared as an attractive s
ynthon for both solid and solution phase peptide synthesis. Its use fo
r the synthesis of Fmoc-Phe-Pro(F)-OMe and Fmoc-Pro(F)-Val-Val-OMe is
presented. Direct fluorination with DAST of a 4-hydroxy proline residu
e incorporated into a peptide and elongation from the terminal amino g
roup allowed preparation of the hexapeptide Boc-Ala-Ala-Phe-Pro(F)-Val
-Val-OMe, analogous to the p17-p24 gag junction of structural HIV prot
eins. None of the fluoropeptides in the paper displayed anti-protease
or anti-HIV activity.