Copyright © 1996, 1997, 2000, 2001 by Galen Daryl Knight and VitaleTherapeutics, Inc.


Indications in the Sulfenate-Linked Benzyl Derivative's (SLBCD) mass spectra of tenacious coordination with water is supported by the proton NMR spectra and elemental analysis of authentic samples of its calcium oxide complex. In the early elemental analysis of authentic compound, a quarter of a mole of residual water per mole of the benzyl derivative complex (essentially, a partially hydrated sulfenate-linked dimer) produces a calculated elemental analysis that agrees very closely with the experimental values observed by Ruby Ju in the Department of Chemistry at UNM. The two moles of water per mole of dimer observed later are presumed to have been taken on from the atmosphere in the several years of storage and handling of this otherwise stable sample, i.e., between the times that the elemental analysis and the mass spectrometry were performed.

By comparison, neither alleged sulfonate analogue, CBZ-ß-alanyl-taurine nor ß-alanyl-taurine, has a calculated elemental analysis consistent with the observed values for the authentic compounds. Elemental analyses and melting points for these alleged sulfonate analogues have not been provided by others for comparison. Results of Dr. Wallace's elemental analysis, when he allegedly attempted to make the authentic SLBCD, were provided. Comparison of his elemental analysis with that for the the authentic compound illustrates that his attempt failed to make the authentic sulfenate-linked benzyl carbamate dimer, the most likely explanation for his results being that the ZnO was volatilized upon lyophilization, incomplete dehydration and an alternate decomposition by loss of cysteamine's sulfenic acid probably being responsible for the differences between Dr. Wallace's elemental analyses and those expected for the dehydrated authentic compound.

As indicated by the elemental analysis performed by Ruby Ju and proton NMR performed by Dr. Cary Morrow, vitaletheine V4 also seems to coordinate water. Although water conceivably stabilizes the carbonimidic structures, it theoretically can also facilitate rearrangements and decarboxylation of this potent modulator, especially when stabilizing salts are disrupted by polar solvents such as DMSO. Storing under anhydrous conditions or vacuum normally can be used to prevent such reactions, but there are now suspicions that vitaletheine V4 may be adversely affected by these manipulations as well. The elemental analysis for the zinc salt of vitaletheine V4 reported in the patents supports this contention. If one considers that one sixth of the zinc metal present in the vitaletheine V4 complex is volatilized (sublimed as the zinc oxide in the course of preparing, lightly drying under vacuum, and analyzing), then the calculated elemental analysis agrees even more favorably with the observed data collected by Ruby Ju than was previously reported. Differences in oxygen determinations when zinc is present (and when appropriate safeguards are not taken to account for these losses) tend to confirm that ZnO easily volatilizes. This well-known sublimation of zinc oxide may explain failures by others to obtain meaningful elemental analyses of their zinc salts. They admittedly have exposed their preparations of the vitaletheine modulators to much stronger vacuums, lyophilization in some instances, for extended periods of time. Storage of these compounds as the published hydrate and under ambient or even hyperbaric pressure is recommended until more stable complexes can be devised, with the realization that hyperbaric oxygen may hasten autoxidation and hyperbaric carbon dioxide may help to preserve carbamates and carbonimidates. Calcium salts may be more resistant to sublimation losses, but calcium salts are excellent drying agents and might predispose toward dehydration, as indicated for the SLBCD under conditions approaching anhydrous. The stability of the calcium complex of vitaletheine V4 under completely anhydrous conditions has not been systematically investigated, but theoretically it should be more stable to hypobaric and anhydrous conditions and less stable to thiol-mediated rearrangement than the corresponding zinc complex.


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