Conserved biosynthetic pathways for phosalacine, bialaphos and newly discovered phosphonic acid natural products

The Journal of Antibiotics
Joshua A V BlodgettWilliam W Metcalf

Abstract

Natural products containing phosphonic or phosphinic acid functionalities often display potent biological activities with applications in medicine and agriculture. The herbicide phosphinothricin-tripeptide (PTT) was the first phosphinate natural product discovered, yet despite numerous studies, questions remain surrounding key transformations required for its biosynthesis. In particular, the enzymology required to convert phosphonoformate to carboxyphosphonoenolpyruvate and the mechanisms underlying phosphorus methylation remain poorly understood. In addition, the model for non-ribosomal peptide synthetase assembly of the intact tripeptide product has undergone numerous revisions that have yet to be experimentally tested. To further investigate the biosynthesis of this unusual natural product, we completely sequenced the PTT biosynthetic locus from Streptomyces hygroscopicus and compared it with the orthologous cluster from Streptomyces viridochromogenes. We also sequenced and analyzed the closely related phosalacine (PAL) biosynthetic locus from Kitasatospora phosalacinea. Using data drawn from the comparative analysis of the PTT and PAL pathways, we also evaluate three related recently discovered phosphonate biosynthetic loci...Continue Reading

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Citations

Feb 24, 2016·Frontiers in Genetics·Angélica Cibrián-Jaramillo, Francisco Barona-Gómez
Oct 28, 2016·Chemical Reviews·Geoff P Horsman, David L Zechel
Mar 23, 2017·Angewandte Chemie·Roderich D Süssmuth, Andi Mainz
Apr 18, 2019·Communications Biology·Venkadesh Sarkarai NadarMasafumi Yoshinaga
Jul 10, 2019·Journal of Molecular Biology·Timothy A Wencewicz
Mar 4, 2020·Journal of Agricultural and Food Chemistry·Chengzeng ZhouJiangtao Gao
Jan 12, 2020·Communications Biology·Venkadesh Sarkarai NadarMasafumi Yoshinaga
Aug 12, 2021·Microbiology Spectrum·Adriana E GalvánMasafumi Yoshinaga
Aug 11, 2021·Chembiochem : a European Journal of Chemical Biology·Simanga R GamaDavid L Zechel

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Datasets Mentioned

BETA
KP026916
KP185121
AHZ58300.1

Software Mentioned

InterProScan
NRPSpredictor
VectorNTI Advance
AntiSmash
ClustalW
AlignX
ESPRIPT
GeneMark
Sequencher
FASTA

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