62623-68-1Relevant articles and documents
Deciphering the late steps of rifamycin biosynthesis
Qi, Feifei,Lei, Chao,Li, Fengwei,Zhang, Xingwang,Wang, Jin,Zhang, Wei,Fan, Zhen,Li, Weichao,Tang, Gong-Li,Xiao, Youli,Zhao, Guoping,Li, Shengying
, (2018/06/26)
Rifamycin-derived drugs, including rifampin, rifabutin, rifapentine, and rifaximin, have long been used as first-line therapies for the treatment of tuberculosis and other deadly infections. However, the late steps leading to the biosynthesis of the industrially important rifamycin SV and B remain largely unknown. Here, we characterize a network of reactions underlying the biosynthesis of rifamycin SV, S, L, O, and B. The two-subunit transketolase Rif15 and the cytochrome P450 enzyme Rif16 are found to mediate, respectively, a unique C-O bond formation in rifamycin L and an atypical P450 ester-to-ether transformation from rifamycin L to B. Both reactions showcase interesting chemistries for these two widespread and well-studied enzyme families.
Process Investigations on the One-Pot Synthesis of Rifamycin S Avoiding Chlorinated Solvents
L?w, Sebastian A.,Nestl, Bettina M.,Weissenborn, Martin J.,Zepeck, Ferdinand,Hauer, Bernhard
, p. 1544 - 1547 (2015/12/01)
The facile synthesis of rifamycin S from rifamycin B, a member of the ansamycin family of antibiotics, via the oxidation of rifamycin B was developed. Currently on an industrial scale, this oxidation is performed using harsh pH conditions and chlorinated solvents. With the development of a suitable buffer/methanol system, a similar yield and space-time-yield in comparison to the current process can be obtained renouncing chlorinated solvents. Employment of methanol as a reaction medium in this process is crucial for attaining high yields under mild reaction conditions. With this method a space-time-yield of 189 g L-1 h-1 of rifamycin S was achieved in one step.
Studies on the total synthesis of rifamycin. A method for the closure of the macrocyclic unit
Corey,Clark
, p. 2045 - 2048 (2007/10/02)
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