In vivo characterization of NcsB3 to establish the complete biosynthesis of the naphthoic acid moiety of the neocarzinostatin chromophore.

Publisher: Oxford University Press Country of Publication: England NLM ID: 7705721 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1574-6968 (Electronic) Linking ISSN: 03781097 NLM ISO Abbreviation: FEMS Microbiol Lett Subsets: MEDLINE

Publication: 2015- : Oxford Oxford University Press
Original Publication: Amsterdam, Published by Elsevier/North Holland on behalf of the Federation of European Microbiological Societies.

Anti-Bacterial Agents/*biosynthesis ; Bacterial Proteins/*metabolism ; Carboxylic Acids/*metabolism ; Cytochrome P-450 Enzyme System/*metabolism ; Naphthalenes/*metabolism ; Streptomyces/*metabolism; Anti-Bacterial Agents/chemistry ; Bacterial Proteins/genetics ; Biosynthetic Pathways ; Carboxylic Acids/chemistry ; Cytochrome P-450 Enzyme System/genetics ; Gene Expression Regulation, Bacterial ; Molecular Structure ; Naphthalenes/chemistry ; Streptomyces/chemistry ; Streptomyces/enzymology ; Zinostatin/analogs & derivatives ; Zinostatin/biosynthesis ; Zinostatin/chemistry

Neocarzinostatin (NCS) is an enediyne antibiotic produced by Streptomyces carzinostaticus. The NCS chromophore consists of an enediyne core, a sugar moiety, and a naphthoic acid (NA) moiety. The latter plays a key role in binding the NCS chromophore to its apoprotein to protect and stabilize the bioactive NCS chromophore. In this study, we expressed three genes: ncsB (naphthoic acid synthase), ncsB3 (P450 hydroxylase), and ncsB1 (O-methyltransferase), in Streptomyces lividans TK24. The three genes were sufficient to produce 2-hydroxy-7-methoxy-5-methyl-1-naphthoic acid. Production was analyzed and confirmed by LC-MS and nuclear magnetic resonance. Here, we report the functional characterization of ncsB3 and thereby elucidate the complete biosynthetic pathway of NA moiety of the NCS chromophore.
(© 2010 Federation of European Microbiological Societies. Published by Blackwell Publishing Ltd. All rights reserved.)

0 (Anti-Bacterial Agents)
0 (Bacterial Proteins)
0 (Carboxylic Acids)
0 (Naphthalenes)
2NIV4O66BH (1-naphthoic acid)
81604-85-5 (neocarzinostatin chromophore)
9014-02-2 (Zinostatin)
9035-51-2 (Cytochrome P-450 Enzyme System)

Date Created: 20100826 Date Completed: 20110105 Latest Revision: 20121115

20231215

10.1111/j.1574-6968.2010.02075.x

20735485