Talaropeptides A-D: Structure and Biosynthesis of Extensively N -methylated Linear Peptides From an Australian Marine Tunicate-Derived Talaromyces sp

Frontiers in Chemistry
Pradeep DewapriyaRobert J Capon

Abstract

An Australian marine tunicate-derived fungus, Talaromyces sp. CMB-TU011 was subjected to a program of analytical microbioreactor (MATRIX) cultivations, supported by UHPLC-QTOF profiling, to reveal conditions for producing a new class of extensively N-methylated 11-12 residue linear peptides, talaropeptides A-D (2-5). The structures for 2-5, inclusive of absolute configurations, were determined by a combination of detailed spectroscopic and chemical (e.g., C3 and C18 Marfey's) analyses. We report on the biological properties of 2-5, including plasma stability, as well as antibacterial, antifungal and cell cytotoxicity. The talaropeptide mega non-ribosomal peptide synthetase (NRPS) is described, as second only in size to that for the fungus-derived immunosuppressant cyclosporine (an 11-residue extensively N-methylated cyclic peptide).

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Citations

Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Apr 26, 2019·Biotechnology Letters·Pengchao ZhaoShuxiao Feng
Jun 3, 2021·Marine Drugs·Chatragadda RameshLaurent Dufossé
Dec 16, 2020·The Journal of Organic Chemistry·Osama G MohamedRobert J Capon

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Methods Mentioned

BETA
NMR
DNA-Seq
acetylation

Software Mentioned

TopSpin
SPAdes
Abyss
Artemis Genome Browser
Fungal
pFAM
Conserved Domain Search
GraphPad
AntiSMASH
Trimmomatic

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