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A maldiisotopic approach to discover natural products: Cryptomaldamide, a hybrid tripeptide from the marine cyanobacterium Moorea producens

TitleA maldiisotopic approach to discover natural products: Cryptomaldamide, a hybrid tripeptide from the marine cyanobacterium Moorea producens
Publication TypeJournal Article
Year of Publication2017
AuthorsKinnel R.B, Esquenazi E., Leao T., Moss N., Mevers E., Pereira A.R, Monroe E.A, Korobeynikov A., Murray T.F, Sherman D., Gerwick L, Dorrestein PC, Gerwick WH
JournalJournal of Natural Products
Volume80
Pagination1514-1521
Date Published2017/05
Type of ArticleArticle
ISBN Number0163-3864
Accession NumberWOS:000402498300034
Keywordsacids; Biosynthetic gene clusters; channel; cytotoxic peptides; hemiasterlin; inhibitors; lyngbya-majuscula; saxitoxin; spectra
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 N-15-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 that 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.

DOI10.1021/acs.jnatprod.7b00019
Short TitleJ. Nat. Prod.
Student Publication: 
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