10 Octopusより得られる鉄錯体ペプチドAdenochromeの化学
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概要
- 論文の詳細を見る
Adenochrome, the iron (III)-containing pigment from the branchial heart of Octopus vulgaris, has been isolated as colorless des ferri-adenochrome (DFA) and shown to consist of a mixture of closely related peptides formed from glycine and two novel amino acids, adenochromines A (1a) and B (1b), the ratio of glycine to adenochro mines being 2: 1. On acid hydrolysis with 6M-HCl-4% thioglycolic acid DFA gave glycine and adenochromines (1), along with some secoadenochromines (2) and the thiol (3) which proved to be derived from (1) by an unusual cleavage of thioether bonds (Scheme 1). Hydrolysis of DFA with 57% HI-red phosphorous yielded glycine, L-dopa (5), and 5-thiol-L-histidine (3; N^1 being partially methylated) in a molar ratio of 2: 1: 2. Further information on the structure of (1) was provided by hydrolysis of (1a) or (1b) with 48% HBr-4% thioglycolic acid which gave, besides (3) and (5), secoadenochromine A (2a). Moreover, on air oxidation of the two isomers only (1a) is converted to an amino chrome-like pigment (Fig.2), suggesting that position 6 is unsubstitute. Adenochromines (1) may be formed in vivo by addition of 5-thiohistidine (3) to dopaquinone arising from tyrosine by tyrosinase oxidation (Scheme 2), as in model experiments the same reaction gave (1) and (2). Of particular biological significance are the findings that the same adenochrome occurs in various parts of Octopus and that a possible biosynthetic precursor is found in the white body which might be the site of biosynthesis.
- 天然有機化合物討論会の論文
- 1976-09-20
著者
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伊藤 祥輔
Stazione Zoologica Di Napoli And Universita Di Napoli
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Nardi Giovanna
Stazione Zoologica di Napoli and Universita di Napoli
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Prota Giuseppe
Stazione Zoologica di Napoli and Universita di Napoli