Enzymatic Synthesis of Dehydroderivatives from Proline-Containing Cyclic Dipeptides and Their Effects toward Cell Division

Panarat ARUNRATTIYAKORN; Banri IKEDA; Teruhiko NITODA; Hiroshi KANZAKI

doi:10.1271/bbb.60651

Organic Chemistry Note

Enzymatic Synthesis of Dehydroderivatives from Proline-Containing Cyclic Dipeptides and Their Effects toward Cell Division

Panarat ARUNRATTIYAKORN, Banri IKEDA, Teruhiko NITODA, Hiroshi KANZAKI

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Keywords: dehydro cyclic dipeptide, enzymatic conversion, inhibitor of cell division, diketopiperazine, albonoursin

JOURNAL FREE ACCESS

2007 Volume 71 Issue 3 Pages 830-833

DOI https://doi.org/10.1271/bbb.60651

View "Advance Publication" version (March 7, 2007).

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Abstract

We have previously isolated cyclo(L-Pro-L-Tyr) and cyclo(L-Phe-L-Pro) from an actinomycete by a novel enzymatic conversion-guided method. Their tetradehydro derivatives, cyclo(ΔPro-ΔTyr) and cyclo(ΔPhe-ΔPro), were enzymatically prepared. Neither of them inhibited cell division, in contrast to other tetradehydro cyclic dipeptides prepared previously. This result suggests that an NH proton in a diketopiperazine ring and/or conformation of the compound are important for the activity.

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