N-methylphenylalanyl-dehydrobutyrine diketopiperazine, an A-factor mimic that restores antibiotic biosynthesis and morphogenesis in Streptomyces globisporus 1912-B2 and Streptomyces griseus 1439

Bohdan Matselyukh, Fatemeh Mohammadipanah, Hartmut Laatsch, Jürgen Rohr, Olga Efremenkova, Volodymyr Khilya

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25 Scopus citations

Abstract

The cell-free extracts of a landomycin E-producing strain, Streptomyces globisporus 1912-2, were shown to contain a low-molecular-weight compound that, like A-factor, restored the landomycin E and streptomycin biosynthesis and sporulation of the defective mutants S. globisporus 1912-B2 and S. griseus 1439, respectively. The compound was purified by thin layer chromatography and HPLC. It had an absorption maximum at λ max =245 nm and a molecular mass of m/z 244. On the basis of NMR spectroscopy (1 H, 13 C, HSQC, HMBC, COSY and NOE) the chemical structure of the compound was elucidated as 6-benzyl-3-eth-(Z)-ylidene-1-methyl-piperazine-2,6-dione ((L)-N-methylphenylalanyl-dehydrobutyrine diketopiperazine (MDD)). The sequences of arpA genes in S. globisporus 1912-2 and S. griseus NBRC 13350 are highly conserved. An explanation for the observed biological activity of MDD was proposed.

Original languageEnglish
Pages (from-to)9-14
Number of pages6
JournalJournal of Antibiotics
Volume68
Issue number1
DOIs
StatePublished - Jan 2015

Bibliographical note

Publisher Copyright:
© 2015 Japan Antibiotics Research Association All rights reserved.

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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