Isolation and Biosynthesis of an Azoxyalkene Compound Produced by a Multiple Gene Disruptant of Streptomyces rochei

CHEMBIOCHEM Volume 16 Issue 15 Page 2237-2243 published_at 2015-10-12
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Title ( eng )
Isolation and Biosynthesis of an Azoxyalkene Compound Produced by a Multiple Gene Disruptant of Streptomyces rochei
Kunitake Hirofumi
Hiramatsu Takahiro
Kinashi Haruyasu
Source Title
Volume 16
Issue 15
Start Page 2237
End Page 2243
Streptomyces rochei 7434AN4 predominantly produces lankacidin and lankamycin under normal culture conditions, suggesting that other biosynthetic gene clusters for secondary metabolites are silent. To exploit silent metabolites of strain 7434AN4, we constructed mutant KA57, a multiple disruptant of the transcriptional repressor gene srrB together with the biosynthesis genes for both antibiotics. Mutant KA57 accumulated a compound (KA57-A) with a strong UV absorption at 235 nm, which was not detected in the parent strain or other mutants. Various spectroscopic analyses revealed that KA57-A is an azoxyalkene compound of a molecular formula of C10H20N2O3 with the R configuration at C-2. Biosynthesis of KA57-A was also studied by feeding with labeled acetates, amino acids, and 1-hexylamine. The hexenyl moiety (C1’-C6’) was derived from fatty acid, while the 3-amino-butan-1,2-diol moiety (C1-C4) was derived from C-2 of acetate (C1) and serine (C2-C4). Incorporation of [1,1-2H2]1-hexylamine indicated that C1’-C2’ dehydrogenation occurs at the final step of biosynthesis.
genetic engineering
natural products
This work was supported by a Grants‐in‐Aid for Scientific Research on Innovative Areas from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), and a Noda Institute for Scientific Research Grant.
Supporting information for this articleis available on the WWW under
Resource Type journal article
Wiley‐VCH Verlag
Date of Issued 2015-10-12
© 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
This is the peer reviewed version of the following article: CHEMBIOCHEM. 2015 Oct 12;16(15):2237-2243, which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
This is not the published version. Please cite only the published version. この論文は出版社版ではありません。引用の際には出版社版をご確認、ご利用ください。
Publish Type Author’s Original
Access Rights open access
Source Identifier
[ISSN] 1439-4227
[ISSN] 1439-7633
[DOI] 10.1002/cbic.201500393
[PMID] 26300120