Evidence for the conversion of adenosine to 2'-deoxycoformycin by Streptomyces antibioticus.
The incorporation and distribution of 14C in 2'-deoxycoformycin, elaborated by Streptomyces antibioticus, were studied with [U-14C]glycine, [U-14C]adenosine and [U-14C]adenine. Similar ratios of 14C in the aglycon and carbohydrate portions of 2'-deoxycoformycin, ara-A, and adenosine isolated from the RNA indicated that [U-14C]adenosine was incorporated into 2'-deoxycoformycin without cleavage of the N-glycosylic bond. Following the addition of [U-14C]adenine, 98% of the 14C isolated from [14C]-2'-deoxycoformycin resided in the aglycon. 2'-Deoxycoformycin biosynthesis may not require the de novo purine biosynthetic pathway as evidenced by the failure to detect incorporation of [U-14C]glycine into 2'-deoxycoformycin. These data suggest that the biosynthesis of 2'-deoxycoformycin involves the incorporation of the carbon-nitrogen skeleton of an intact purine nucleoside or nucleotide, thereby implying that a purine ring is opened enzymatically between C-6 and N-1 and a one-carbon unit is added to form the 1,3-diazepine ring of 2'-deoxycoformycin.
D000225:Adenine / Q000378:metabolism; D000241:Adenosine / Q000378:metabolism*; D058892:Adenosine Deaminase Inhibitors; D002250:Carbon Radioisotopes; D002855:Chromatography, Thin Layer; D003070:Coformycin / Q000031:analogs & derivatives / Q000096:biosynthesis* / Q000302:isolation & purification; D003561:Cytarabine / Q000302:isolation & purification; D005998:Glycine / Q000378:metabolism; D015649:Pentostatin; D012263:Ribonucleosides / Q000096:biosynthesis*; D013302:Streptomyces / Q000378:metabolism*
D058892:Adenosine Deaminase Inhibitors; D002250:Carbon Radioisotopes; D012263:Ribonucleosides; D003561:Cytarabine; D003070:Coformycin; D015649:Pentostatin; D000225:Adenine; D000241:Adenosine; D005998:Glycine