Structure of thioviridamide, a novel apoptosis inducer from Streptomyces olivoviridis.
A novel apoptosis inducer, thioviridamide, was isolated from an actinomycete identified as Streptomyces olivoviridis. The molecular formula of thioviridamide was determined to be C56H93N14O10S7+ from high-resolution FAB-MS. The structure of thioviridamide was analyzed by NMR spectral analysis including a variety of two-dimensional techniques. COSY and HMBC experiments revealed the presence of a 2-hydroxy-2-methyl-4-oxopentanoyl group and eleven amino acid residues including two novel amino acids, beta-hydroxy-N1,N3-dimethylhistidinium and S-(2-aminovinyl)cysteine. 1H-13C long-range correlations observed in the HMBC, CT-HMBC and HMBC-HOHAHA spectra connected the partial structures with seven amide linkages and five thioamide linkages to establish the planar structure of thioviridamide as a unique cyclic peptide.
Hayakawa
Yoichi
Y
Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan. hykw@rs.noda.tus.ac.jp
Sasaki
Kahori
K
Nagai
Koji
K
Shin-ya
Kazuo
K
Furihata
Kazuo
K
D000596:Amino Acids / Q000032:analysis; D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013854:Thioamides / Q000737:chemistry*
D000596:Amino Acids; D000903:Antibiotics, Antineoplastic; D010456:Peptides, Cyclic; D013854:Thioamides; C509635:thioviridamide