Isolation of cyclic deoxyadenosine 3':5'-monophosphate from the culture fluid of Corynebacterium murisepticum No. 7.

Nucleic acid related compounds. 27. "Virtual coupling" of the anomeric proton of cyclic 2'-deoxynucleoside 3',5'-monophosphates. Reassessment of conformation using praseodymium shifts and assignment of H-2',2 signals by biomimetic deuteration at C-2'

“…The solution was evaporated, the residue was stirred with «-hexane, and the insoluble product was filtered and washed well on the Filter with «-hexane. This white product (605 mg, 92%) had mp 225-227 °C (lit.31 mp [225][226] °C for the protio compound) and was homogeneous by the TLC system indicated: NMR (CDC13, Me4Si internal) 2.30 (br t, 0.76, H-2'), 2.72 (m, 0.24, H-2"), 4.57 (m, 1, H-4'), 4.72 (m, 2, H-5', H-5"), 5.62 (m, 2, H-3', H-5), 6.40 (d,y,-_2-= 8 Hz, 1, H-L), 7.51 (m, 7, H-6, m-and p-benzoyl protons), 8.05 (m, 4, o-benzoyl protons), 8.79 (br s, 1, NH-3); mass spectrum caled for M+ (C23H,9DN207) 437.1333, found m/e 437.1337.…”

“…The isolation of cdAMP from a bacterial culture fluid has been noted very recently. 7 We have been interested in the valuable potential of these cyclic nucleotides to reveal C-T-C-2' configuration patterns. Examination of the usually well-separated H-1' NMR signal is definitive for assignment of the anomeric cNMP's owing to the geometrical constraints of the trans-fused sixto fivemembered phosphodiester furanose backbone.1 Determination Journal of the American Chemical Society / 99:14 / July 6, 1977 of the overall stereochemistry of enzymatic conversion of ribonucleotides to their 2'-deoxy (DNA) counterparts by ribonucleotide reductases was accomplished only after considerable manipulation and syntheses.8 Application of our new use of cNMP derivatives for H-l' to H-2' configuration assignment1 to cdNMP derivatives makes this problem easilv amenable to experimental investigation.…”