Use of the dehydrophos biosynthetic enzymes to prepare antimicrobial analogs of alaphosphin

Bougioukou, Despina J.; Ting, Chi P.; Peck, Spencer C.; Mukherjee, Subha; Donk, Wilfred A. van der

doi:10.1039/c8ob02860e

Cited by 7 publications

(2 citation statements)

References 42 publications

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“…Thus, it was considered as a lead compound for the design of novel antibacterial agents [88]. The non-typical and innovative is the application of its biosynthetic enzymes for obtaining new antibacterial phosphonopeptides [89]. Recently, the role of nonribosomal peptidyl transferase DhpH in the formation of peptide bond in dehydrophos was studied in detail using phosphonic analog of alanine and various amino acid-tRNAs as substrates [90].…”

Section: Phosphonopeptide Antibioticsmentioning

confidence: 99%

Phosphonates: Their Natural Occurrence and Physiological Role

Kafarski¹

2020

Contemporary Topics About Phosphorus in Biology and Materials

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The first natural compound containing carbon-to-phosphorus bond-ciliatine was discovered 60 years ago, and for four decades, phosphonates were considered simply as a biological curiosity. Finding the importance of these compounds in biogeochemical phosphorus cycling, their role in methane production, as well as discovery of numerous phosphonates and phosphonopeptides of promising antibacterial and antifungal activities has stimulated the development of studies on this class of compounds, especially on their metabolism and biochemistry. These studies are driven by the use of 31 P NMR and by a clever combination of genomics and innovative chemistry by using the method of selective labeling of metabolites. These studies revealed unusual and interesting chemistry of these compounds.

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Section: Phosphonopeptide Antibioticsmentioning

confidence: 99%

Phosphonates: Their Natural Occurrence and Physiological Role

Kafarski¹

2020

Contemporary Topics About Phosphorus in Biology and Materials

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“…This enzyme is highly tolerant to structural variations in both aminoacyl-tRNAs and aminophosphonic acids and was used for the preparation of series phosphonodipeptides of interesting antibacterial properties. 35 Quite original, approach was used to the synthesis of natural phosphono peptidedehydrophos (Fig. 5).…”

Section: B Peptides Containing C-terminal Aminophosphonic Acidsmentioning

confidence: 99%