A New Diketopiperazine,Cyclo(D- trans -Hyp-L-Leu) from a Kenyan Bacterium Bacillus licheniformis LB 8C T

Abstract

Bacterially-produced small molecules demonstrate a wide range of structural and functional diversity. A new diketopiperazine, cyclo(D-trans-Hyp-L-Leu) (1), and five other known diketopiperazines (2–6), were isolated and purified from the fermented broth of a Kenyan bacterium Bacillus licheniformis LB 8C^T. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including 2D NMR and HR-MS, and the absolute configuration was determined by a combination of NOESY analysis and Marfey's method. The known compounds were identified as cyclo(D-cis-Hyp-L-Leu) (2), cyclo(D-cis-Hyp-L-Phe) (3), cyclo(D-Pro-L-Tyr) (4), cyclo-(D-Trp-L-Leu) (5), and cyclo(L-Tyr-Gly) (6) by comparison of their spectroscopic and physical data with reported values. Compounds 1–6 were tested for antifungal and antimicrobial properties.