Ring formation in a pentapeptide with alternating L and D residues: An analogy to cyclization in the biosynthesis of peptide antibiotics.

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  • Ring formation in a pentapeptide with a

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Acetylation of L-isoleucyl-D-alanyl-D-alanyl-L-valyl-D-leucine with acetic anhydride followed by methylation with diazomethane yielded the expected acetylpentapeptide methyl ester with molecular weight 541, but also resulted in the formation of a by-product with molecular weight 555. The incorporation of the mass corresponding to CH<sub>2<sub> seems to be due to ring closure-via a mixed anhydride-and methylation of the cyclol derivative thus formed. A preferred, ring-like conformation stabilized by intramolecular hydrogen bonds that in turn are the consequences of the alternation of D- and L- residues in the sequence, is invoked as explanation for the unexpected cyclization. This assumption is supported by the conversion of the pentapeptide methyl ester to desthiomalformin in molten imidazole.

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