Peptide Epimerization Machineries Found in Microorganisms

Frontiers in Microbiology
Yasushi Ogasawara, Tohru Dairi

Abstract

D-Amino acid residues have been identified in peptides from a variety of eukaryotes and prokaryotes. In microorganisms, UDP-N-acetylmuramic acid pentapeptide (UDP-MurNAc-L-Ala-D-Glu-meso-diaminopimelate-D-Ala-D-Ala), a unit of peptidoglycan, is a representative. During its biosynthesis, D-Ala and D-Glu are generally supplied by racemases from the corresponding isomers. However, we recently identified a unique unidirectional L-Glu epimerase catalyzing the epimerization of the terminal L-Glu of UDP-MurNAc-L-Ala-L-Glu. Several such enzymes, introducing D-amino acid resides into peptides via epimerization, have been reported to date. This includes a L-Ala-D/L-Glu epimerase, which is possibly used during peptidoglycan degradation. In bacterial primary metabolisms, to the best of our knowledge, these two machineries are the only examples of peptide epimerization. However, a variety of peptides containing D-amino acid residues have been isolated from microorganisms as secondary metabolites. Their biosynthetic mechanisms have been studied and three different peptide epimerization machineries have been reported. The first is non-ribosomal peptide synthetase (NRPS). Excellent studies with dissected modules of gramicidin synthetase and ty...Continue Reading

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Citations

Nov 5, 2019·Organic & Biomolecular Chemistry·Bin LiuKaifeng Hu
Jan 8, 2021·ACS Synthetic Biology·Madlen KorneliJörn Piel
Mar 4, 2021·Organic Letters·Liujuan ZhengShu-Ming Li
Oct 2, 2020·Biochimica Et Biophysica Acta. Proteins and Proteomics·David H MastJonathan V Sweedler
Apr 7, 2021·Journal of the American Chemical Society·Sayaka ImanishiHiroaki Suga
Oct 27, 2021·Interdisciplinary Sciences, Computational Life Sciences·Qian YuTing Shi

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Methods Mentioned

BETA
X-ray
NMR
PCR

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