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Review

Natural Products Containing ‘Rare’ Organophosphorus Functional Groups

1
Department of Earth, Atmospheric, and Planetary Sciences, Massachusetts Institute of Technology, 77 Mass. Ave., Cambridge, MA 02139, USA
2
Rufus Scientific, 37 The Moor, Melbourn, Royston, Herts SG8 6ED, UK
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Department of Physics, Massachusetts Institute of Technology, 77 Mass. Ave., Cambridge, MA 02139, USA
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Department of Aeronautics and Astronautics, Massachusetts Institute of Technology, 77 Mass. Ave., Cambridge, MA 02139, USA
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Author to whom correspondence should be addressed.
Molecules 2019, 24(5), 866; https://doi.org/10.3390/molecules24050866
Received: 21 January 2019 / Revised: 13 February 2019 / Accepted: 22 February 2019 / Published: 28 February 2019
(This article belongs to the Section Natural Products Chemistry)
Phosphorous-containing molecules are essential constituents of all living cells. While the phosphate functional group is very common in small molecule natural products, nucleic acids, and as chemical modification in protein and peptides, phosphorous can form P–N (phosphoramidate), P–S (phosphorothioate), and P–C (e.g., phosphonate and phosphinate) linkages. While rare, these moieties play critical roles in many processes and in all forms of life. In this review we thoroughly categorize P–N, P–S, and P–C natural organophosphorus compounds. Information on biological source, biological activity, and biosynthesis is included, if known. This review also summarizes the role of phosphorylation on unusual amino acids in proteins (N- and S-phosphorylation) and reviews the natural phosphorothioate (P–S) and phosphoramidate (P–N) modifications of DNA and nucleotides with an emphasis on their role in the metabolism of the cell. We challenge the commonly held notion that nonphosphate organophosphorus functional groups are an oddity of biochemistry, with no central role in the metabolism of the cell. We postulate that the extent of utilization of some phosphorus groups by life, especially those containing P–N bonds, is likely severely underestimated and has been largely overlooked, mainly due to the technological limitations in their detection and analysis. View Full-Text
Keywords: P–N bond; phosphoramidate; N-phosphorylation; P–S bond; phosphorothioate; S-phosphorylation; P–C bond; phosphonate; phosphinate; phosphine P–N bond; phosphoramidate; N-phosphorylation; P–S bond; phosphorothioate; S-phosphorylation; P–C bond; phosphonate; phosphinate; phosphine
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MDPI and ACS Style

Petkowski, J.J.; Bains, W.; Seager, S. Natural Products Containing ‘Rare’ Organophosphorus Functional Groups. Molecules 2019, 24, 866. https://doi.org/10.3390/molecules24050866

AMA Style

Petkowski JJ, Bains W, Seager S. Natural Products Containing ‘Rare’ Organophosphorus Functional Groups. Molecules. 2019; 24(5):866. https://doi.org/10.3390/molecules24050866

Chicago/Turabian Style

Petkowski, Janusz J.; Bains, William; Seager, Sara. 2019. "Natural Products Containing ‘Rare’ Organophosphorus Functional Groups" Molecules 24, no. 5: 866. https://doi.org/10.3390/molecules24050866

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