Literature DB >> 15489167

Novel avilamycin derivatives with improved polarity generated by targeted gene disruption.

Gabriele Weitnauer1, Gerd Hauser, Carsten Hofmann, Ulrike Linder, Raija Boll, Klaus Pelz, Steffen J Glaser, Andreas Bechthold.   

Abstract

The oligosaccharide antibiotics avilamycin A and C are produced by Streptomyces viridochromogenes Tu57. Both consist of a heptasaccharide chain, which is attached to a polyketide-derived dichloroisoeverninic acid moiety. They show excellent antibiotic activity against Gram-positive bacteria. Both molecules are modified by O-methylation at different positions, which contributes to poor water solubility and difficulties in galenical drug development. In order to generate novel avilamycin derivatives with improved polarity and improved pharmacokinetic properties, we generated a series of mutants with one, two, or three mutated methyltransferase genes. Based on the structure of the novel avilamycin derivatives, the exact function of three methyltransferases, AviG2, AviG5, and AviG6, involved in avilamycin biosynthesis could be assigned.

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Year:  2004        PMID: 15489167     DOI: 10.1016/j.chembiol.2004.08.016

Source DB:  PubMed          Journal:  Chem Biol        ISSN: 1074-5521


  10 in total

Review 1.  A comprehensive review of glycosylated bacterial natural products.

Authors:  Sherif I Elshahawi; Khaled A Shaaban; Madan K Kharel; Jon S Thorson
Journal:  Chem Soc Rev       Date:  2015-11-07       Impact factor: 54.564

Review 2.  Radical S-adenosylmethionine enzymes.

Authors:  Joan B Broderick; Benjamin R Duffus; Kaitlin S Duschene; Eric M Shepard
Journal:  Chem Rev       Date:  2014-01-29       Impact factor: 60.622

3.  Avilamycin and evernimicin induce structural changes in rProteins uL16 and CTC that enhance the inhibition of A-site tRNA binding.

Authors:  Miri Krupkin; Itai Wekselman; Donna Matzov; Zohar Eyal; Yael Diskin Posner; Haim Rozenberg; Ella Zimmerman; Anat Bashan; Ada Yonath
Journal:  Proc Natl Acad Sci U S A       Date:  2016-10-19       Impact factor: 11.205

4.  Statistical optimization of medium components for avilamycin production by Streptomyces viridochromogenes Tü57-1 using response surface methodology.

Authors:  Chuan-He Zhu; Fu-Ping Lu; Ya-Nan He; Juan-Kun Zhang; Lian-Xiang Du
Journal:  J Ind Microbiol Biotechnol       Date:  2006-12-21       Impact factor: 3.346

5.  The Structure of the Bifunctional Everninomicin Biosynthetic Enzyme EvdMO1 Suggests Independent Activity of the Fused Methyltransferase-Oxidase Domains.

Authors:  C A Starbird; Nicole A Perry; Qiuyan Chen; Sandra Berndt; Izumi Yamakawa; Lioudmila V Loukachevitch; Emilianne M Limbrick; Brian O Bachmann; T M Iverson; Kathryn M McCulloch
Journal:  Biochemistry       Date:  2018-12-07       Impact factor: 3.162

6.  Structures of the orthosomycin antibiotics avilamycin and evernimicin in complex with the bacterial 70S ribosome.

Authors:  Stefan Arenz; Manuel F Juette; Michael Graf; Fabian Nguyen; Paul Huter; Yury S Polikanov; Scott C Blanchard; Daniel N Wilson
Journal:  Proc Natl Acad Sci U S A       Date:  2016-06-21       Impact factor: 11.205

Review 7.  Bioactive oligosaccharide natural products.

Authors:  Emilianne K McCranie; Brian O Bachmann
Journal:  Nat Prod Rep       Date:  2014-08       Impact factor: 13.423

Review 8.  Iterative polyketide biosynthesis by modular polyketide synthases in bacteria.

Authors:  Haotong Chen; Liangcheng Du
Journal:  Appl Microbiol Biotechnol       Date:  2015-11-09       Impact factor: 4.813

9.  The dTDP-4-dehydro-6-deoxyglucose reductase encoding fcd gene is part of the surface layer glycoprotein glycosylation gene cluster of Geobacillus tepidamans GS5-97T.

Authors:  Sonja Zayni; Kerstin Steiner; Andreas Pföstl; Andreas Hofinger; Paul Kosma; Christina Schäffer; Paul Messner
Journal:  Glycobiology       Date:  2007-01-03       Impact factor: 4.313

Review 10.  Microbial Oligosaccharides with Biomedical Applications.

Authors:  Jian-Lin Xu; Zhi-Feng Liu; Xiao-Wei Zhang; Hai-Li Liu; Yong Wang
Journal:  Mar Drugs       Date:  2021-06-21       Impact factor: 5.118

  10 in total

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