New Insights into Rifamycin B Biosynthesis: Isolation of Proansamycin B and 34a-Deoxy-rifamycin W as Early Macrocyclic Intermediates Indicating Two Separated Biosynthetic Pathways.
-
- STRATMANN ANSGAR
- Novartis Pharma AG, Research, Drug Discovery Center and Central Technologies BUGH Wuppertal, FB9, Chemische Mikrobiologie
-
- SCHUPP THOMAS
- Novartis Pharma AG, Research, Drug Discovery Center and Central Technologies
-
- TOUPET CHRISTIANE
- Novartis Pharma AG, Research, Drug Discovery Center and Central Technologies
-
- SCHILLING WOLFGANG
- Novartis Pharma AG, Research, Drug Discovery Center and Central Technologies
-
- OBERER LUKAS
- Novartis Pharma AG, Research, Drug Discovery Center and Central Technologies
-
- TRABER RENÉ
- Novartis Pharma AG, Research, Drug Discovery Center and Central Technologies
この論文をさがす
説明
Proansamycin B, the formerly postulated intermediate of rifamycin B biosynthesis, was isolated from cultures of the Amycolatopsis mediterranei mutant F1/24. The structure was determined using UV, IR, NMR and MS techniques. Biotransformation studies demonstrate that proansamycin B is an intermediate of a shunt pathway, a 8-deoxy variant, of rifamycin B biosynthesis leading to 8-deoxy-rifamycin B as the final product.<br>In addition, 34a-deoxy-rifamycin W, the direct precursor of rifamycin W, could be isolated representing the earliest macrocyclic intermediate obtained so far in the biosynthetic route to rifamycin B. Furthermore, the new rifamycin W-28-desmethyl-28-carboxy and rifamycin W-hemiacetal, intermediates in, the transformation sequence of rifamycin W to rifamycin S, were isolated. Application of proton NMR measurements (double resonance and ROESY experiments) on the latter compound indicated that the stereochemistry at the chiral center C-28 is R.
収録刊行物
-
- The Journal of Antibiotics
-
The Journal of Antibiotics 55 (4), 396-406, 2002
公益財団法人 日本感染症医薬品協会