2′-Deoxycoformycin: Biosynthesis and Enzymatic Conversion of 8-Keto-Deoxycoformycin to 2′-Deoxycoformycin by Streptomyces Antibioticus

Abstract

Studies on t h e biosynthesis o f the N-nucleoside antibiotics have established that the purine and pyrimidine nucleosides/nucleotides serve as the carbon and nitrogen skeleton, whereas with the C-nucleoside antibioticus, the C-N precursor forthe aglycon is either acetate or glutamate. With the pyrrolopyrimidine nucleoside antibiotics (toyocamycin, tubercidin, and sangi vamycin), either two or three carbons of the N-riboside/ribotide of GTP contribute to carbons 5 and 6 of the pyrrolering and the cyano or carboxamide group. With the naturally occurring nucleoside antibiotic containing the 1,3-diazepine seven-membered ring,2′-deoxycoformycin (dCF)(I), the precursor is not immediately obvious.