Herein, we describe the synthesis and MR characterization of a pioneering metal‐free 31P‐MR probe based on phosphorus‐containing polymeric zwitterion. However, due to the low physiological level of phosphorus‐containing biomolecules, precise imaging requires the administration of an exogenous probe. 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.ģ1P‐magnetic resonance (MR) is an important diagnostic technique currently used for tissue metabolites assessing, but it also has great potential for visualizing the internal body structures.

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. 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. Information on biological source, biological activity, and biosynthesis is included, if known. In this review we thoroughly categorize P–N, P–S, and P–C natural organophosphorus compounds. While rare, these moieties play critical roles in many processes and in all forms of life. 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.

Phosphorous-containing molecules are essential constituents of all living cells.

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