Can anyone help with literature on reactions of Glyphosate, N-(phosphonomethyl)glycine), or its degradation products such as (Aminomethyl)phosphonic acid with Fluoride, HF or Fluorine? Material safety data sheets simply state that they are incompatible with Fluorine. Of interest are reports of complexes of Uranium and Europium where Glyphosate and Fluoride are brought into close proximity. This brings into question the wider subject of Fluoride attack on Phosphorus in biological systems and the basis of observed epigenetic interference with human genes.
Dear Geoff,
I had a look at material safety data sheet of Glyphosate and it states that this compound is sensitive to fluorine due to high oxidation potential of F2.
This seems reasonable as C-P bond in Glyphosate looks like something that can get oxidised. I have found a couple of articles supporting this hypothesis:
Article Oxidative Degradation of Glyphosate and Aminomethylphosphona...
Article Degradation and Detoxification of Organophosphonates: Cleava...
The MSDS is just about meaningless. Virtually everything reacts with fluorine, and free fluorine is unlikely to be around except in specialist laboratories.
I found that direct Phosphorus-Fluoride bonds can be made under mild conditions and pH 7 in RNA that includes Imidazole leaving groups. This is very worrying and could be part of the explanation for the observed attack on over 2000 Human genes with links to over 1700 disease conditions reported in the US NIEHS Chemical Toxicity database. See this exciting paper:
Article The reaction of activated RNA species with aqueous fluoride ...
Related to this discussion is the publication of a prebiotically plausible synthesis of adenosine-5′-phosphorimidazolide (R=H), using a photochemically generated activating agent. Article Prebiotic nucleic acids need space to grow
Another elegant approach to P-F bond formation under mild conditions.
Aldersley MF, Joshi PC, Ott EL, McCallum SA, Kirby AJ. 2015.
The introduction of P-F bonds using aqueous fluoride ion and a water soluble carbodiimide: a convenient alternative synthesis of phosphorofluoridates and phosphonofluoridates Tetrahedron Letters http://dx.doi.org/10.1016/j.tetlet.
2015.07.036
Methoxy Arachidonyl FluoroPhosphonate, commonly referred as MAFP, is an irreversible active site-directed enzyme inhibitor against hundreds of your enzymes coded by over 1% of your entire genome. How many such molecules with P-F bonds are formed inside your body when you ingest Fluoride?
An interesting aspect of the FluoroPhosphonates used to detect and inhibit hundreds of enzymes is their chirality. This one can easily pass through cellular membranes and the alkyne function can be used to attach fluorescent probes. Gillet LCK et al. 2008. In-cell Selectivity Profiling of Serine Protease Inhibitors by Activity-based Proteomics. Molecular & Cellular Proteomics. 7(7):1241-1253
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