Chemical studies on amphotericin B II. 2-methylheptadecanedioic acid from perhydrogenated amphotericin B

✍ Scribed by E. Borowski; W. Mechliński; L. Falkowski; T. Zimiński; J.D. Dutcher

• Book ID: 104223141
• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 202 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89982-7

✦ Synopsis

Amphotericdn B is a heptaenic macrolide antifungal antibiotic with a tentative empirical formula Q,HT302dy and molecular weight of 960 (1,2). It yields ngrcosamine on hydrolysis (2) and belongs to structural subgroup of heptaenes (3). In the course of our studies on the structure of oxldative degradation of perhydrogenated amphotericin the non-aromatic this substance, B was carried out in order to isolate a large fragment which would contain the hydrocarbon chain corresponding to the original heptaenic portion of the antibiotic. Perhydroamphoterlcln B (2,&) was aridload with nitric acid (d m lb) In acetic acid at 100 C or with potassium permangsnate under alkaline conditions at room temperature followed by further oxidation with chromic acid in acetic acid at 65 -70 C. The crude products MM first purlflsd by cellulose colunm chroutography In the solvent system, tetrahydrofuran: 3 N aawonla (8:l). and crystallised from 80 percent acetic acid. The *73