Cadeguomycin, a novel nucleoside analog antibiotic. II. Improved purification, physicochemical properties and structure assessment.

Cadeguomycin, a new nucleoside analog antibiotic, has been purified as colorless needle crystals by recycling preparative HPLC. The antibiotic, C12H14O7N4, mp 231-239°C (dec.), FD-MS: m/z 326 (M+); is a weakly acidic substance, showing UV λH2Omax (e) 232 (19677), 272 (6881) and 298 nm (7607), and IR νKBrmax 1650 (C=O) and 3420 (NH or OH) cm-1. The UV spectrum is similar to other pyrrolo[2, 3-d]pyrimidines. The structure of cadeguomycin, 2-amino-3, 4-dihydro-4-oxo-7-β-D-ribofuranosyl-7H-pyrrolo[2, 3-d]pyrimidine-5-carboxyalcicid, has been elucidated by 1H NMR and 13C NMR in comparison with other pyrrolo[2, 3-d]pyrimidines and their nucleosides.