SNA-60-367 components, new peptide enzyme inhibitors of aromatase: Structure of the fatty acid side chain and amino acid sequence by mass spectrometry

Abstract

SNA-60-367 components, new peptide enzyme inhibitors of aromatase, were isolated from the culture broth of soil bacterium, Bacillus sp. SNA-60-367. These inhibitors are a family of acylated decapeptides that differ from each other in terms of amino acid composition and the nature of the fatty acid side chain. The structures of the fatty acid moieties were shown to be (3-hydroxy)heptadecanoic acid and (3-hydroxy)hexadecanoic acid that possess normal-, iso- or anteiso-type alkyl groups. The amino acid sequence of the open form of the lactone ring of the acylpeptides is RCO-L-Glu-D-Orn-L(or D)-Tyr3-D-allo-Thr-L-Glu-D-X1 (Ala, Aba or Val -L-Pro-L-Gln-D(or L)-Tyr-L-X210(Ile or Val)-OH. The lactone ring of SNA-60-367 components is formed between Tyr3 and X210.