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

VitaleTheine Modulators

The vitaletheine modulators provide an interesting array of stabilities and biological activities. Generally, the oxidized versions, such as the disulfide, vitalethine, and its benzyl derivative (the bis-benzyl derivative of a sulfenic acid dimer) have tumor-negating activities at relatively low concentrations. In non-oxidizing environments, vitaletheine and its polymerized tetramer are thought to have primarily proliferative activities. Theoretically this system can result in proliferation through at least two possible scenarios:
  1. Direct activation of HMG-CoA reductase by thiols (including vitaletheine or glutathione); or
  2. When the monooxygenase is compromised, diverted by other substrates, or in an inactivating aggregation with the tetramer, vitaletheine V4.
Treatment with the tetramer increases melanoma growth in the allogeneic model and enhances red blood cell formation from erythroid progenitors, indicating that this type of regulation is important in the control of both normal and cancer cells.

The stability of these compounds from the most chemically dynamic to the most stable are as follows: vitaletheine, vitaletheine V4, vitalethine, and the sulfenate-linked benzyl derivative of vitalethine. For example, vitaletheine is almost too reactive to chemically analyze in an environment not stabilized by proteinaceous receptors, yet the sulfenate-linked benzyl derivative of vitalethine shows no signs of thermal decomposition or melting until well over 300 degrees (Centigrade).


Although vitalethine appears stable for years when frozen as a powder, its synthesis is not trivial. In the approximately five years that it took to perfect the reported synthesis, many solvent systems and strategies for producing free carbamic acid or imidocarbonate moieties were attempted. None of the other procedures tested to date have produced the pristine material obtained using the reported procedure and additional tips on synthesis included in this Web Page.

Bis-Benzyl Sulfenate-Linked Dimer

Anyone want to have a stab at chemical nomenclature for this beast? A comparison of the infrared spectra for this benzyl derivative with the spectra of vitalethine and of bis-CBZ-ß-alethine are very enlightening, particularly around the C-O stretch regions.

VitaleTheine V4

The tetramer may slowly rearrange when not stored under anhydrous conditions, but storage of the zinc salt of this compound under anhydous conditions and/or reduced pressures can also lead to dehydration through sublimation of ZnO and rehydration to a different product.


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