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J Am Chem Soc. 2006 Jun 14;128(23):7486-91.

Lariatins, antimycobacterial peptides produced by Rhodococcus sp. K01-B0171, have a lasso structure.

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Kitasato Institute, Kitasato University, Minato-ku, Tokyo 108, Japan.


Two antimycobacterial agents, lariatins A and B, were isolated from the culture broth of Rhodococcus sp. K01-B0171. Their structures were elucidated by spectral analysis and advanced protein chemical methods to be unique cyclic peptides, which consist of 18 and 20 L-amino acid residues with an internal linkage between the gamma-carboxyl group of Glu8 and the alpha-amino group of Gly1. The three-dimensional structure of lariatin A deduced from NMR data by dynamical simulated annealing method indicates that the tail segment (Trp9-Pro18) passes through the ring segment (Gly1-Glu8) to form a 'lasso' structure.

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