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螺旋诺卡氏菌 IMC A-0156 中吡拉霉素生物合成的遗传学研究。

Genetic insights into pyralomicin biosynthesis in Nonomuraea spiralis IMC A-0156.

机构信息

Department of Pharmaceutical Sciences, Oregon State University, Corvallis, OR 97331-3507, United States.

出版信息

J Nat Prod. 2013 May 24;76(5):939-46. doi: 10.1021/np400159a. Epub 2013 Apr 22.

Abstract

The biosynthetic gene cluster for the pyralomicin antibiotics has been cloned and sequenced from Nonomuraea spiralis IMC A-0156. The 41 kb gene cluster contains 27 ORFs predicted to encode all of the functions for pyralomicin biosynthesis. This includes nonribosomal peptide synthetases (NRPS) and polyketide synthases (PKS) required for the formation of the benzopyranopyrrole core unit, as well as a suite of tailoring enzymes (e.g., four halogenases, an O-methyltransferase, and an N-glycosyltransferase) necessary for further modifications of the core structure. The N-glycosyltransferase is predicted to transfer either glucose or a pseudosugar (cyclitol) to the aglycone. A gene cassette encoding C7-cyclitol biosynthetic enzymes was identified upstream of the benzopyranopyrrole-specific ORFs. Targeted disruption of the gene encoding the N-glycosyltransferase, prlH, abolished pyralomicin production, and recombinant expression of PrlA confirms the activity of this enzyme as a sugar phosphate cyclase involved in the formation of the C7-cyclitol moiety.

摘要

已从链霉菌(Nonomuraea spiralis)IMC A-0156 中克隆并测序了吡拉霉素抗生素的生物合成基因簇。该 41kb 的基因簇包含 27 个 ORF,预测编码吡拉霉素生物合成所需的所有功能。这包括形成苯并吡喃并吡咯核心单元所需的非核糖体肽合酶(NRPS)和聚酮合酶(PKS),以及一套修饰酶(例如,四个卤化酶、一个 O-甲基转移酶和一个 N-糖基转移酶),这些酶对于核心结构的进一步修饰是必要的。该 N-糖基转移酶预计将葡萄糖或假糖(环醇)转移到糖苷配基上。在苯并吡喃并吡咯特异性 ORF 的上游鉴定到了编码 C7-环醇生物合成酶的基因盒。靶向破坏编码 N-糖基转移酶(prlH)的基因导致吡拉霉素生产被废除,而重组表达 PrlA 证实了该酶作为参与 C7-环醇部分形成的糖磷酸环化酶的活性。

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本文引用的文献

1
Evolutionary divergence of sedoheptulose 7-phosphate cyclases leads to several distinct cyclic products.
J Am Chem Soc. 2012 Jul 25;134(29):12219-29. doi: 10.1021/ja3041866. Epub 2012 Jul 5.
2
Complete genome sequence of Streptosporangium roseum type strain (NI 9100).
Stand Genomic Sci. 2010 Jan 28;2(1):29-37. doi: 10.4056/sigs.631049.
3
The genetic and molecular basis for sunscreen biosynthesis in cyanobacteria.
Science. 2010 Sep 24;329(5999):1653-6. doi: 10.1126/science.1193637. Epub 2010 Sep 2.
4
Genome sequence of the milbemycin-producing bacterium Streptomyces bingchenggensis.
J Bacteriol. 2010 Sep;192(17):4526-7. doi: 10.1128/JB.00596-10. Epub 2010 Jun 25.
7
Structure and mechanism of the rebeccamycin sugar 4'-O-methyltransferase RebM.
J Biol Chem. 2008 Aug 15;283(33):22628-36. doi: 10.1074/jbc.M800503200. Epub 2008 May 23.
8
The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp.
Org Lett. 2008 Feb 21;10(4):629-31. doi: 10.1021/ol702952n. Epub 2008 Jan 19.
9
Intelligent control of surface hydrophobicity.
Chemphyschem. 2007 Oct 8;8(14):2036-50. doi: 10.1002/cphc.200700222.

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