Scytodecamide from the Cultured Scytonema sp. UIC 10036 Expands the Chemical and Genetic Diversity of Cyanobactins. (26th November 2019)

• Record Type: Journal Article
• Authors: Crnkovic, Camila M.; Braesel, Jana; Krunic, Aleksej; Eustáquio, Alessandra S.; Orjala, Jimmy
• Is Part Of: Chembiochem. Volume 21:Number 6(2020)
• Page Start: 845
• Page End: 852
• Publication Date: 2019-11-26
• Subjects: biosynthesis -- cyanobacteria -- cyanobactin -- natural products -- RiPP; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.201900511
• Languages: English
• ISSNs: 1439-4227

Abstract

Abstract: Cyanobactins are a large family of cyanobacterial ribosomally synthesized and post‐translationally modified peptides (RiPPs) often associated with biological activities, such as cytotoxicity, antiviral, and antimalarial activities. They are traditionally described as cyclic molecules containing heterocyclized amino acids. However, this definition has been recently challenged by the discovery of short, linear cyanobactins containing three to five amino acids as well as cyanobactins containing no heterocyclized residues. Herein we report the discovery of scytodecamide (1 ) from the freshwater cyanobacterium Scytonema sp. UIC 10036. Structural elucidation based on mass spectrometry, 1D and 2D NMR spectroscopy, and Marfey's method revealed 1 to be a linear decapeptide with an N‐terminal N‐methylation and a C‐terminal amidation. The genome of Scytonema sp. UIC 10036 was sequenced, and bioinformatic analysis revealed a cyanobactin‐like biosynthetic gene cluster consistent with the structure of 1 . The discovery of 1 as a novel linear peptide containing an N‐terminal N‐methylation and a C‐terminal amidation expands the chemical and genetic diversity of the cyanobactin family of compounds. Abstract : Expanding diversity : Scytodecamide is a novel N‐ and C‐protected peptide. Isolated from the freshwater cyanobacterium Scytonema sp. UIC 10036, it is a linear decapeptide featuring N‐terminal N‐methylation and a C‐terminal amidation. Genome sequencing and bioinformatics analysis revealed a cyanobactin biosynthetic gene cluster consistent with the structure of scytodecamide.