Natural Products Containing ‘Rare’ Organophosphorus Functional Groups The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters. Citation Petkowski, Janusz, et al. “Natural Products Containing ‘Rare’ Organophosphorus Functional Groups.” Molecules, vol. 24, no. 5, Feb. 2019, p. 866. As Published http://dx.doi.org/10.3390/molecules24050866 Publisher Multidisciplinary Digital Publishing Institute Version Final published version Citable link http://hdl.handle.net/1721.1/120918 Terms of Use Creative Commons Attribution Detailed Terms https://creativecommons.org/licenses/by/4.0/ molecules Review Natural Products Containing ‘Rare’ Organophosphorus Functional Groups Janusz J. Petkowski 1,* , William Bains 2 and Sara Seager 1,3,4 1 Department of Earth, Atmospheric, and Planetary Sciences, Massachusetts Institute of Technology, 77 Mass. Ave., Cambridge, MA 02139, USA;
[email protected] 2 Rufus Scientific, 37 The Moor, Melbourn, Royston, Herts SG8 6ED, UK;
[email protected] 3 Department of Physics, Massachusetts Institute of Technology, 77 Mass. Ave., Cambridge, MA 02139, USA 4 Department of Aeronautics and Astronautics, Massachusetts Institute of Technology, 77 Mass. Ave., Cambridge, MA 02139, USA * Correspondence:
[email protected] Received: 21 January 2019; Accepted: 22 February 2019; Published: 28 February 2019 Abstract: 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.