Synthesis of a Val-Pro diaminodiol dipeptide isostere by epoxyamine cyclization.
[reaction: see text] The stereoselective synthesis of a novel proline-containing dipeptide isostere is described. Starting from l-valine, three new contiguous stereocenters are generated by asymmetric induction and epoxide chemistry, while the pyrrolidine ring of proline is introduced in the final step via intramolecular ring opening of the amino acid derived epoxyamine. Proline-containing peptidomimetics are potentially attractive as selective inhibitors of proline-specific enzymes, such as PPIases and retroviral proteases, and as analogues of bioactive peptides.
Benedetti
Fabio
F
Department of Chemical Sciences and Center of Excellence for Biocrystallography, University of Trieste, via Giorgieri 1, I-34127 Trieste, Italy. benedett@units.it
Berti
Federico
F
Dinon
Francesca
F
Nardin
Giorgio
G
Norbedo
Stefano
S