The structure of a novel nucleoside antibiotic, dapiramicin A

NMR fingerprints, an integrated approach to uncover the unique components of the drug-like natural product metabolome of termite gut-associated Streptomyces species

“…These correlations were consistent with the presence of a purine residue which was further conrmed by NMR data comparison with related natural products containing the same residue such as dapiramicins A and B. 27,28 Crucial HMBC correlations from the anomeric proton (H-1 0 ) to the quaternary carbon (C-2) indicated that fragment A and B are connected through a nitrogen atom. 3) displayed eight resonances attributable to two sp 3 -hybridized methylenes at d H 4.12 (2H, s, H-7) and six sp 2 -hybridized methines at d H 7.31 (2H, dd, J ¼ 7.9, 5.6 Hz, H-2), 7.19 (2H, dd, J ¼ 7.3, 5.6 Hz, H-3), 7.28 (1H, dd, J ¼ 7.9, 5.6 Hz, H-4), 8.46 (1H, s, H-9).…”

Microbial Transformation of Sampangine

“…This downfield shift was attributed to the presence of an O -methyl group on C-4‘, which resonated in the 13 C NMR spectrum at δ 60.8 and in the 1 H NMR spectrum at δ 3.6 (s, 3H). This conclusion was further confirmed by comparing the 13 C resonances of the sugar part with those reported for the corresponding carbons in similar 4‘- O -methylglucopyranoside …”

A comprehensive review of glycosylated bacterial natural products

“…924,925 Dapiramicins A and B from Micromonospora are N -glycosidic pyrrolopyrimidines bearing 6′-deoxy-α-D-glucose ( 215 ) or β-D-glucose ( 104 ), respectively, each capped (β1→4) with 4′-methyl-β-D-glucose ( 104 ). 926,927 The α-configured dapiramicin A with disaccharide IV possessed significantly higher activity against the plant disease, sheath blight than the analog bearing V .…”