Structural Revision of Natural Cyclic Depsipeptide MA026 Established by Total Synthesis and Biosynthetic Gene Cluster Analysis

2021 ◽  
Vol 133 (16) ◽  
pp. 8874-8879
Author(s):  
Chihiro Uchiyama ◽  
Akane Fukuda ◽  
Minagi Mukaiyama ◽  
Yoshiki Nakazawa ◽  
Yuka Kuramochi ◽  
...  
Keyword(s):  
Cluster Analysis ◽  
Total Synthesis ◽  
Gene Cluster ◽  
Biosynthetic Gene Cluster ◽  
Biosynthetic Gene ◽  
Structural Revision ◽  
Cyclic Depsipeptide

scholarly journals Cloning and Characterization of the Biosynthetic Gene Cluster for Tomaymycin, an SJG-136 Monomeric Analog

2009 ◽  
Vol 75 (9) ◽  
pp. 2958-2963 ◽  
Author(s):  
Wei Li ◽  
ShenChieh Chou ◽  
Ankush Khullar ◽  
Barbara Gerratana
Keyword(s):  
Cluster Analysis ◽  
Gene Cluster ◽  
Biosynthetic Pathway ◽  
Biosynthetic Gene Cluster ◽  
Gene Replacement ◽  
Biosynthetic Gene

ABSTRACT Tomaymycin produced by Streptomyces achromogenes is a naturally produced pyrrolobenzodiazepine (PBD). The biosynthetic gene cluster for tomaymycin was identified and sequenced. The gene cluster analysis reveals a novel biosynthetic pathway for the anthranilate moiety of PBDs. Gene replacement and chemical complementation studies were used to confirm the proposed biosynthetic pathway.

Structure elucidation and biosynthetic gene cluster analysis of caniferolides A–D, new bioactive 36-membered macrolides from the marine-derived Streptomyces caniferus CA-271066

2019 ◽  
Vol 17 (11) ◽  
pp. 2954-2971 ◽  
Author(s):  
Ignacio Pérez-Victoria ◽  
Daniel Oves-Costales ◽  
Rodney Lacret ◽  
Jesús Martín ◽  
Marina Sánchez-Hidalgo ◽  
...  
Keyword(s):  
Cluster Analysis ◽  
Gene Cluster ◽  
Absolute Configuration ◽  
Structure Elucidation ◽  
Biosynthetic Gene Cluster ◽  
Biosynthetic Gene ◽  
The Absolute

The structures of caniferolides A–D have been determined combining NMR and bioinformatics prediction of the absolute configuration.

scholarly journals Bottromycins - biosynthesis, synthesis and activity

2021 ◽  
Author(s):  
Laura Franz ◽  
Uli Kazmaier ◽  
Andrew W. Truman ◽  
Jesko Koehnke
Keyword(s):  
Total Synthesis ◽  
Heterologous Expression ◽  
Gene Cluster ◽  
Mechanism Of Action ◽  
Structure Elucidation ◽  
Biosynthetic Gene Cluster ◽  
Biosynthetic Enzymes ◽  
Biosynthetic Gene ◽  
The 1950S ◽  
Activity Mechanism

This review summarizes bottromycin research from the 1950s to 2020, including structure elucidation, activity, mechanism of action, total synthesis, biosynthetic gene cluster and biosynthesis, biosynthetic enzymes and heterologous expression.

Biosynthetic Gene Cluster Analysis in Actinobacterial Genus Streptomyces

2022 ◽  
pp. 247-262
Author(s):  
Markéta Macho ◽  
Daniela Ewe ◽  
Vishal Ahuja ◽  
Jihen Thabet ◽  
Avik Banerjee ◽  
...  
Keyword(s):  
Cluster Analysis ◽  
Gene Cluster ◽  
Biosynthetic Gene Cluster ◽  
Biosynthetic Gene ◽  
Genus Streptomyces

Anacyclamide D8P, a prenylated cyanobactin from a Sphaerospermopsis sp. cyanobacterium

2017 ◽  
Author(s):  
Joana Martins ◽  
Niina Leikoski ◽  
Matti Wahlsten ◽  
Joana Azevedo ◽  
Jorge Antunes ◽  
...  
Keyword(s):  
Gene Cluster ◽  
Cyclic Peptides ◽  
Biosynthetic Gene Cluster ◽  
The Novel ◽  
Tyrosine Residue ◽  
Biosynthetic Gene ◽  
Post Translational Modification ◽  
Biological Assays ◽  
Mass Spectrometric Data ◽  
Spectrometric Data

Cyanobactins are a family of linear and cyclic peptides produced through the post-translational modification of short precursor peptides. Anacyclamides are macrocyclic cyanobactins with a highly diverse sequence that are common in the genus <i>Anabaena</i>. A mass spectrometry-based screening of potential cyanobactin producers led to the discovery of a new prenylated member of this family of compounds, anacyclamide D8P (<b>1</b>), from <i>Sphaerospermopsis</i> sp. LEGE 00249. The anacyclamide biosynthetic gene cluster (<i>acy</i>) encoding the novel macrocyclic prenylated cyanobactin, was sequenced. Heterologous expression of the acy gene cluster in <i>Escherichia</i> <i>coli</i> established the connection between genomic and mass spectrometric data. Unambiguous establishment of the type and site of prenylation required the full structural elucidation of <b>1</b> using Nuclear Magnetic Resonance (NMR), which demonstrated that a forward prenylation occurred on the tyrosine residue. Compound <b>1</b> was tested in pharmacologically or ecologically relevant biological assays and revealed moderate antimicrobial activity towards the fouling bacterium <i>Halomonas aquamarina</i> CECT 5000.<br>

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