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A Maldiisotopic Approach to Discover Natural Products: Cryptomaldamide, a Hybrid Tripeptide from the Marine Cyanobacterium Moorea producens
- Source :
- Journal of Natural Products. 80:1514-1521
- Publication Year :
- 2017
- Publisher :
- American Chemical Society (ACS), 2017.
-
Abstract
- Genome sequencing of microorganisms has revealed a greatly increased capacity for natural products biosynthesis than was previously recognized from compound isolation efforts alone. Hence, new methods are needed for the discovery and description of this hidden secondary metabolite potential. Here we show that provision of heavy nitrogen 15N-nitrate to marine cyanobacterial cultures followed by single filament MALDI analysis over a period of days was highly effective in identifying a new natural product with an exceptionally high nitrogen content. The compound, named cryptomaldamide, was subsequently isolated using MS to guide the purification process, and its structure determined by 2D NMR and other spectroscopic and chromatographic methods. Bioinformatic analysis of the draft genome sequence identified a 28.7 kB gene cluster which putatively encodes for cryptomaldamide biosynthesis. Notably, an amidinotransferase is proposed to initiate the biosynthetic process by transferring an amidino group from arginine to serine to produce the first residue to be incorporated by the hybrid NRPS-PKS pathway. The maldiisotopic approach presented here is thus demonstrated to provide an orthogonal method by which to discover novel chemical diversity from Nature.
- Subjects :
- 0301 basic medicine
Magnetic Resonance Spectroscopy
Pharmaceutical Science
Computational biology
Secondary metabolite
Biology
Cyanobacteria
01 natural sciences
Article
DNA sequencing
Analytical Chemistry
03 medical and health sciences
chemistry.chemical_compound
Biosynthesis
Drug Discovery
Botany
Gene cluster
medicine
Moorea producens
Pharmacology
Whole genome sequencing
Biological Products
Natural product
Molecular Structure
010405 organic chemistry
Organic Chemistry
Computational Biology
biology.organism_classification
0104 chemical sciences
030104 developmental biology
Complementary and alternative medicine
chemistry
Biosynthetic process
Molecular Medicine
Oligopeptides
medicine.drug
Subjects
Details
- ISSN :
- 15206025 and 01633864
- Volume :
- 80
- Database :
- OpenAIRE
- Journal :
- Journal of Natural Products
- Accession number :
- edsair.doi.dedup.....1e44c8fd855f57bb518c8597842be1d9