title: Revised structure of cyclolithistide A, a cyclic depsipeptide from the marine sponge Discodermia japonica.
abstract: A cyclic peptide was isolated from the deep-sea marine sponge Discodermia japonica, and its NMR spectroscopic data were identical to those reported for cyclolithistide A, a known antifungal depsipeptide. However, the interresidue HMBC correlations suggested that the amino acid sequence was different from that of the original structure. Moreover, chiral-phase GC-MS, combined with Marfey's analysis, indicated that the absolute configurations of three amino acids were also antipodal. Here, we propose the revised structure of cyclolithistide A and address the configuration of the previously unassigned 4-amino-3,5-dihydroxyhexanoic acid (Adha) moiety.
authors: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors: Hiroki
authors: H
authors: Tajima
authors: Toshiyuki
authors: T
authors: Wakimoto
authors: Kentaro
authors: K
authors: Takada
authors: Yuji
authors: Y
authors: Ise
authors: Ikuro
authors: I
authors: Abe
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry* / Q000302:isolation & purification; D047630:Depsipeptides / Q000737:chemistry* / Q000302:isolation & purification; D008401:Gas Chromatography-Mass Spectrometry; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D047630:Depsipeptides; C587412:cyclolithistide A; C087123:romidepsin