Pluta P L, Crespi H L, Klein M, Blake M I, Studier M H, Katz J J
J Pharm Sci. 1976 Mar;65(3):362-6. doi: 10.1002/jps.2600650311.
The riboflavin-producing fungus Eremothecium ashbyii was cultured in various growth media containing high concentrations of deuteriuj, and the product was isolated. The structures of highly deuterated riboflavin, in which at least 13 of 15 nonexchangeable hydrogens were replaced by deuterium, and fully deuterated riboflavin, in which all 15 nonexchangeable sites contained deuterium, were established by NMR and mass spectrometry. The aromatic protons (C-5 and C-8) wer partially substituted in the highly deuterated molecule. Information regarding three areas of the biosynthetic pathway within the microorganism was obtained as a result of the formation of these compounds. Extensive solvent interaction, possibly due to passage of sugar through the transaldolase-transketolase pathway, occurs during formation of the ribityl chain. Limited solvent participation takes place during formation of 6,7-dimethyl-8-ribityllumazine, the immediate precursor of riboflavin. Deuteration of the riboflavin C-6 and C-7 methyl groups indicates significant solvent exchange during the final step of the biosynthetic process.
在含有高浓度氘的各种生长培养基中培养产核黄素的真菌阿氏酵母，并分离产物。通过核磁共振（NMR）和质谱确定了高氘代核黄素（其中15个不可交换氢中的至少13个被氘取代）和全氘代核黄素（其中所有15个不可交换位点都含有氘）的结构。在高氘代分子中，芳香质子（C-5和C-8）被部分取代。由于这些化合物的形成，获得了有关微生物生物合成途径三个区域的信息。在核糖醇链形成过程中发生广泛的溶剂相互作用，这可能是由于糖通过转醛醇酶-转酮醇酶途径所致。在核黄素的直接前体6,7-二甲基-8-核糖基异咯嗪形成过程中，溶剂参与有限。核黄素C-6和C-7甲基的氘代表明在生物合成过程的最后一步有明显的溶剂交换。
