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核糖基化利福平及其衍生物的结构测定：分枝杆菌菌株产生的利福平新的失活代谢产物

Structure determination of ribosylated rifampicin and its derivative: new inactivated metabolites of rifampicin by mycobacterial strains.

作者信息

Morisaki N, Kobayashi H, Iwasaki S, Furihata K, Dabbs E R, Yazawa K, Mikami Y

机构信息

Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.

出版信息

J Antibiot (Tokyo). 1995 Nov;48(11):1299-303. doi: 10.7164/antibiotics.48.1299.

DOI:10.7164/antibiotics.48.1299
PMID:8557572
Abstract

Rifampicin (I) was converted into two inactivated products RIP-Ma and RIP-Mb by Mycobacterium smegmatis DSM43756. MS, NMR and chromatographic analysis showed the compounds to be 3-formyl-23-[O-(alpha-D-ribofuranosyl)]rifamycin SV (6) and 23-[O-(alpha-D-ribofuranosyl)]rifampicin (7), respectively.

摘要

利福平（I）被耻垢分枝杆菌DSM43756转化为两种失活产物RIP-Ma和RIP-Mb。质谱、核磁共振和色谱分析表明，这两种化合物分别为3-甲酰基-23-[O-(α-D-呋喃核糖基)]利福霉素SV（6）和23-[O-(α-D-呋喃核糖基)]利福平（7）。

相似文献

1
Structure determination of ribosylated rifampicin and its derivative: new inactivated metabolites of rifampicin by mycobacterial strains.核糖基化利福平及其衍生物的结构测定：分枝杆菌菌株产生的利福平新的失活代谢产物
J Antibiot (Tokyo). 1995 Nov;48(11):1299-303. doi: 10.7164/antibiotics.48.1299.
2
Structures of ADP-ribosylated rifampicin and its metabolite: intermediates of rifampicin-ribosylation by Mycobacterium smegmatis DSM43756.ADP-核糖基化利福平及其代谢产物的结构：耻垢分枝杆菌DSM43756对利福平进行核糖基化的中间体
J Antibiot (Tokyo). 2000 Mar;53(3):269-75. doi: 10.7164/antibiotics.53.269.
3
Inactivated products of rifampicin by pathogenic Nocardia spp.: structures of glycosylated and phosphorylated metabolites of rifampicin and 3-formylrifamycin SV.
J Antibiot (Tokyo). 1993 Oct;46(10):1605-10. doi: 10.7164/antibiotics.46.1605.
4
Identification and characterization of a new intermediate in the ribosylative inactivation pathway of rifampin by Mycobacterium smegmatis.耻垢分枝杆菌对利福平核糖基化失活途径中一种新中间体的鉴定与表征。
Microb Drug Resist. 1999 Winter;5(4):259-64. doi: 10.1089/mdr.1999.5.259.
5
Phosphorylative inactivation of rifampicin by Nocardia otitidiscaviarum.
J Antimicrob Chemother. 1994 Jun;33(6):1127-35. doi: 10.1093/jac/33.6.1127.
6
ADP-ribosylation as an intermediate step in inactivation of rifampin by a mycobacterial gene.ADP-核糖基化作为分枝杆菌基因使利福平失活的中间步骤。
Antimicrob Agents Chemother. 1999 Jan;43(1):181-4. doi: 10.1128/AAC.43.1.181.
7
Ribosylation by mycobacterial strains as a new mechanism of rifampin inactivation.分枝杆菌菌株的核糖体糖基化作用作为利福平失活的一种新机制。
Antimicrob Agents Chemother. 1995 Apr;39(4):1007-9. doi: 10.1128/AAC.39.4.1007.
8
Light inhibits rifampicin inactivation and reduces rifampicin resistance due to a cloned mycobacterial ADP-ribosylation gene.光照可抑制利福平失活，并降低因克隆的分枝杆菌ADP-核糖基化基因导致的利福平耐药性。
FEMS Microbiol Lett. 2000 Jan 1;182(1):105-9. doi: 10.1111/j.1574-6968.2000.tb08882.x.
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Accumulation of rifampicin by Mycobacterium aurum, Mycobacterium smegmatis and Mycobacterium tuberculosis.金色分枝杆菌、耻垢分枝杆菌和结核分枝杆菌对利福平的摄取
J Antimicrob Chemother. 2000 Feb;45(2):159-65. doi: 10.1093/jac/45.2.159.
10
Reactive rifampicin derivative able to damage transcription complex.能够破坏转录复合物的反应性利福平衍生物。
Bioconjug Chem. 2013 Mar 20;24(3):443-7. doi: 10.1021/bc3005667. Epub 2013 Mar 1.

引用本文的文献

1
Integrative metagenomic and biochemical studies on rifamycin ADP-ribosyltransferases discovered in the sediment microbiome.整合宏基因组学和生物化学研究揭示了沉积物微生物组中发现的利福霉素 ADP-核糖基转移酶。
Sci Rep. 2018 Aug 14;8(1):12143. doi: 10.1038/s41598-018-30547-x.
2
Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr.通过ADP-核糖基化产生的利福霉素抗生素耐药性：Arr的结构与多样性
Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4886-91. doi: 10.1073/pnas.0711939105. Epub 2008 Mar 18.
3
A rifampin-hypersensitive mutant reveals differences between strains of Mycobacterium smegmatis and presence of a novel transposon, IS1623.
一株利福平超敏突变体揭示了耻垢分枝杆菌菌株之间的差异以及一种新型转座子IS1623的存在。
Antimicrob Agents Chemother. 2003 Oct;47(10):3208-13. doi: 10.1128/AAC.47.10.3208-3213.2003.
4
ADP-ribosylation as an intermediate step in inactivation of rifampin by a mycobacterial gene.ADP-核糖基化作为分枝杆菌基因使利福平失活的中间步骤。
Antimicrob Agents Chemother. 1999 Jan;43(1):181-4. doi: 10.1128/AAC.43.1.181.