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Structure-inhibitory activity relationships of pyrrolnitrin analogues on its biosynthesis.
MedLine Citation:
PMID:  20865257     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
Pyrrolnitrin is a bacterial metabolite, served as a natural lead of agricultural fungicides. In a previous study, fenpiclonil was proven to inhibit the oxidative transformation of aminopyrrolnitrin to pyrrolnitrin, catalyzed by aminopyrrolnitrin oxidase (PrnD). This monooxygenase has an interesting catalytic activity of selective oxidation of aromatic amines, rather than aliphatic amines. However, its structural details are not well understood. In this study, various analogues of pyrrolnitrin were prepared to elucidate the structures of active site of PrnD through structure-activity relationships. In vivo pyrrolnitrin biosynthesis inhibition was determined with Burkholderia sp. O33 and Pseudomonas fluorescens Pf-5. Quantitative analysis of pyrrolnitrin and precursors indicates that 2,3-disubstituted phenyl at 3rd carbon and small substituents at 4th carbon of pyrrole are strictly required to give strong inhibitory effects. In addition, dissociable proton of pyrrole is also critical for inhibitory activity. Molecular simulation with homology-based PrnD model suggests a highly restricted conformational space in active site. The results may help more detailed understanding of this unusual enzyme. In addition, the information will be useful for the development of novel fungicide, compatible with pyrrolnitrin-producing bacterium.
Authors:
Young Soo Keum; Yong-Zhe Zhu; Jeong-Han Kim
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Publication Detail:
Type:  Journal Article     Date:  2010-09-24
Journal Detail:
Title:  Applied microbiology and biotechnology     Volume:  89     ISSN:  1432-0614     ISO Abbreviation:  Appl. Microbiol. Biotechnol.     Publication Date:  2011 Feb 
Date Detail:
Created Date:  2011-01-20     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8406612     Medline TA:  Appl Microbiol Biotechnol     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  781-9     Citation Subset:  IM    
Affiliation:
Department of Molecular Biotechnology, College of Life and Environmental Sciences, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul, Republic of Korea, rational@konkuk.ac.kr.
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