Biosynthesis of Rishirilide B

Biosynthesis of Rishirilide B

Rishirilide B was isolated from Streptomyces rishiriensis and Streptomyces bottropensis on the basis of its inhibitory activity towards alpha-2-macroglobulin. The biosynthesis of rishirilide B was investigated by feeding experiments with different 13C labelled precursors using the heterologous host...

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Main Authors: Philipp Schwarzer, Julia Wunsch-Palasis, Andreas Bechthold, Thomas Paululat
Format: Article
Language:English
Published: MDPI AG 2018-03-01
Series:Antibiotics
Subjects:
streptomyces
rishirilide
biosynthesis
polyketides
Online Access:http://www.mdpi.com/2079-6382/7/1/20
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spelling doaj-1834a959048443098357cba70ddb05e02020-11-25T00:34:38ZengMDPI AGAntibiotics2079-63822018-03-01712010.3390/antibiotics7010020antibiotics7010020Biosynthesis of Rishirilide BPhilipp Schwarzer0Julia Wunsch-Palasis1Andreas Bechthold2Thomas Paululat3Pharmaceutical Biology and Biotechnology, University of Freiburg, Stefan-Meier-Str. 19, 79104 Freiburg im Breisgau, GermanyPharmaceutical Biology and Biotechnology, University of Freiburg, Stefan-Meier-Str. 19, 79104 Freiburg im Breisgau, GermanyPharmaceutical Biology and Biotechnology, University of Freiburg, Stefan-Meier-Str. 19, 79104 Freiburg im Breisgau, GermanyOrganic Chemistry, University of Siegen, Adolf-Reichwein-Str. 2, 57068 Siegen, GermanyRishirilide B was isolated from Streptomyces rishiriensis and Streptomyces bottropensis on the basis of its inhibitory activity towards alpha-2-macroglobulin. The biosynthesis of rishirilide B was investigated by feeding experiments with different 13C labelled precursors using the heterologous host Streptomyces albus J1074::cos4 containing a cosmid encoding of the gene cluster responsible for rishirilide B production. NMR spectroscopic analysis of labelled compounds demonstrate that the tricyclic backbone of rishirilide B is a polyketide synthesized from nine acetate units. One of the acetate units is decarboxylated to give a methyl group. The origin of the starter unit was determined to be isobutyrate.http://www.mdpi.com/2079-6382/7/1/20streptomycesrishirilidebiosynthesispolyketides
collection DOAJ
language English
format Article
sources DOAJ
author Philipp Schwarzer
Julia Wunsch-Palasis
Andreas Bechthold
Thomas Paululat
spellingShingle Philipp Schwarzer
Julia Wunsch-Palasis
Andreas Bechthold
Thomas Paululat
Biosynthesis of Rishirilide B
Antibiotics
streptomyces
rishirilide
biosynthesis
polyketides
author_facet Philipp Schwarzer
Julia Wunsch-Palasis
Andreas Bechthold
Thomas Paululat
author_sort Philipp Schwarzer
title Biosynthesis of Rishirilide B
title_short Biosynthesis of Rishirilide B
title_full Biosynthesis of Rishirilide B
title_fullStr Biosynthesis of Rishirilide B
title_full_unstemmed Biosynthesis of Rishirilide B
title_sort biosynthesis of rishirilide b
publisher MDPI AG
series Antibiotics
issn 2079-6382
publishDate 2018-03-01
description Rishirilide B was isolated from Streptomyces rishiriensis and Streptomyces bottropensis on the basis of its inhibitory activity towards alpha-2-macroglobulin. The biosynthesis of rishirilide B was investigated by feeding experiments with different 13C labelled precursors using the heterologous host Streptomyces albus J1074::cos4 containing a cosmid encoding of the gene cluster responsible for rishirilide B production. NMR spectroscopic analysis of labelled compounds demonstrate that the tricyclic backbone of rishirilide B is a polyketide synthesized from nine acetate units. One of the acetate units is decarboxylated to give a methyl group. The origin of the starter unit was determined to be isobutyrate.
topic streptomyces
rishirilide
biosynthesis
polyketides
url http://www.mdpi.com/2079-6382/7/1/20
work_keys_str_mv AT philippschwarzer biosynthesisofrishirilideb
AT juliawunschpalasis biosynthesisofrishirilideb
AT andreasbechthold biosynthesisofrishirilideb
AT thomaspaululat biosynthesisofrishirilideb
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