CHRYSCANDIN, A NOVEL PEPTIDYL NUCLEOSIDE ANTIBIOTIC II. STRUCTURE DETERMINATION AND SYNTHESIS

• Published in: Journal of antibiotics Vol. 37; no. 11; pp. 1284 - 1293
• Main Authors: YAMASHITA, MICHIO, KAWAI, YOSHIO, UCHIDA, ITSUO, KOMORI, TADAAKI, KOHSAKA, MASANOBU, IMANAKA, HIROSHI, SAKANE, KAZUO, SETOI, HIROYUKI, TERAJI, TSUTOMU
• Format: Journal Article
• Language: English
• Published: Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 01.01.1984; Japan Antibiotics Research Association
• Subjects: Antifungal Agents - chemical synthesis; Biological and medical sciences; Chemical Phenomena; Chemistry; General pharmacology; Medical sciences; Pharmacology. Drug treatments; Physicochemical properties. Structure-activity relationships; Puromycin - analogs & derivatives; Puromycin Aminonucleoside - analogs & derivatives; Puromycin Aminonucleoside - chemical synthesis; Spectrum Analysis; Fungi; Antibiotic; Antifungal agent; Peptides; Molecular structure; Preparation; Nucleoside; Thallophyta
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.37.1284

The structure of chryscandin, a novel antifungal antibiotic, produced by Chrysosporium pannorumV No.4629 was deduced to be 1 from spectroscopic and chemical evidences. In order to confirm the structure and to determine the absolute configuration, the total synthesis of chryscandin was performed. D-Xylose was transformed into 10 in ten steps. After β-glycosidation of silylated benzoyl adenine with 10, the resulting 11 was converted into 4, which was identical with the product obtained from chryscandin by alkaline hydrolysis. From the key intermediate 13, chryscandin was synthesized via peptide formation followed by removal of the protecting groups. Chryscandin(1)is the first naturally occurring nucleoside antibiotic possessing a 3-aminoribofuranuronlc acid in the molecule.