Sphaerocyclamide, a prenylated cyanobactin from the cyanobacterium Sphaerospermopsis sp. LEGE 00249

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Martins , J , Leikoski , N , Wahlsten , M , Azevedo , J , Antunes , J , Jokela , J , Sivonen , K , Vasconcelos , V , Fewer , D P & Leão , P N 2018 , ' Sphaerocyclamide, a prenylated cyanobactin from the cyanobacterium Sphaerospermopsis sp. LEGE 00249 ' , Scientific Reports , vol. 8 , no. 1 , 14537 . https://doi.org/10.1038/s41598-018-32618-5

Title: Sphaerocyclamide, a prenylated cyanobactin from the cyanobacterium Sphaerospermopsis sp. LEGE 00249
Author: Martins, Joana; Leikoski, Niina; Wahlsten, Matti; Azevedo, Joana; Antunes, Jorge; Jokela, Jouni; Sivonen, Kaarina; Vasconcelos, Vitor; Fewer, David P.; Leão, Pedro N.
Contributor organization: Department of Microbiology
Cyanobacteria research
Doctoral Programme in Microbiology and Biotechnology
Helsinki Institute of Sustainability Science (HELSUS)
Doctoral Programme in Food Chain and Health
Microbial Natural Products
Date: 2018-09-28
Language: eng
Number of pages: 9
Belongs to series: Scientific Reports
ISSN: 2045-2322
DOI: https://doi.org/10.1038/s41598-018-32618-5
URI: http://hdl.handle.net/10138/298348
Abstract: Cyanobactins are a family of linear and cyclic peptides produced through the post-translational modification of short precursor peptides. A mass spectrometry-based screening of potential cyanobactin producers led to the discovery of a new prenylated member of this family of compounds, sphaerocyclamide (1), from Sphaerospermopsis sp. LEGE 00249. The sphaerocyclamide biosynthetic gene cluster (sph) encoding the novel macrocyclic prenylated cyanobactin, was sequenced. Heterologous expression of the sph gene cluster in Escherichia coli confirmed the connection between genomic and mass spectrometric data. Unambiguous establishment of the orientation and site of prenylation required the full structural elucidation of 1 using Nuclear Magnetic Resonance (NMR), which demonstrated that a forward prenylation occurred on the tyrosine residue. Compound 1 was tested in pharmacologically or ecologically relevant biological assays and revealed moderate antimicrobial activity towards the fouling bacterium Halomonas aquamarina CECT 5000.
Subject: 1183 Plant biology, microbiology, virology
FRESH-WATER CYANOBACTERIUM
MICROCYSTIS-AERUGINOSA
OSCILLATORIA-AGARDHII
CYCLIC UNDECAPEPTIDE
DIVERSITY
KAWAGUCHIPEPTIN
PEPTIDES
STRAINS
PATHWAY
FAMILY
Peer reviewed: Yes
Rights: cc_by
Usage restriction: openAccess
Self-archived version: publishedVersion


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