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Natural Products Containing ‘Rare’ Organophosphorus Functional Groups

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 (phosphorothio...

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Detalles Bibliográficos
Autores principales: Petkowski, Janusz J., Bains, William, Seager, Sara
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6429109/
https://www.ncbi.nlm.nih.gov/pubmed/30823503
http://dx.doi.org/10.3390/molecules24050866
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author Petkowski, Janusz J.
Bains, William
Seager, Sara
author_facet Petkowski, Janusz J.
Bains, William
Seager, Sara
author_sort Petkowski, Janusz J.
collection PubMed
description 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.
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spelling pubmed-64291092019-04-15 Natural Products Containing ‘Rare’ Organophosphorus Functional Groups Petkowski, Janusz J. Bains, William Seager, Sara Molecules Review 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. MDPI 2019-02-28 /pmc/articles/PMC6429109/ /pubmed/30823503 http://dx.doi.org/10.3390/molecules24050866 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Petkowski, Janusz J.
Bains, William
Seager, Sara
Natural Products Containing ‘Rare’ Organophosphorus Functional Groups
title Natural Products Containing ‘Rare’ Organophosphorus Functional Groups
title_full Natural Products Containing ‘Rare’ Organophosphorus Functional Groups
title_fullStr Natural Products Containing ‘Rare’ Organophosphorus Functional Groups
title_full_unstemmed Natural Products Containing ‘Rare’ Organophosphorus Functional Groups
title_short Natural Products Containing ‘Rare’ Organophosphorus Functional Groups
title_sort natural products containing ‘rare’ organophosphorus functional groups
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6429109/
https://www.ncbi.nlm.nih.gov/pubmed/30823503
http://dx.doi.org/10.3390/molecules24050866
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