Synthesis and properties of the cyclopentapeptide desthiomalformin

Desthiomalformin, cyclo-d-alanyl-d-alanyl-l-valyl-d-leucyl-l-isoleucyl, was synthesized by conventional methods. Cyclization of the open chain intermediate through the azide produced the cyclopentapeptide in short reaction time and in high yield and was not accompanied by cyclodimerization. The extreme readiness of the pentapeptide azide to form a cyclic structure can be attributed to the presence of alternating d and l residues in the sequence, a feature that should result in reverse turns stabilized by intramolecular hydrogen bonds. Thus the open chain intermediate could have a preferred cyclic conformation.Desthiomalformin has high thermal stability; it can be sublimed in vacuo without decomposition. It lacks, however, the biological activity of its parent compound, malformin.