By Mulchand S. Patel, Frank Jordan
Thiamine: Catalytic Mechanisms in general and ailment States brings jointly the latest advancements in thiamine diphosphate (TDP)-requiring enzyme examine and info the mechanisms of catalysis and structure-function relationships, in addition to pathophysiological points of a spectrum of ailments linked to TDP-requiring enzymes. offering new insights into neurogenerative illnesses, this quantity affiliates defects within the functionality of TDP-dependent enzymes with a number of metabolic issues and illness states and provides novel points of thiamine enzymes in chiral synthesis in addition to new views at the mobile function of thiamine triphosphate and thiamine triphosphates.
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Extra resources for Thiamine: Catalytic Mechanisms in Normal and Disease States (Oxidative Stress and Disease)
Datta. REFERENCES 1. R Breslow. Rapid deuterium exchange in thiazolium salts. J Am. Chem. Soc. 79:1762–1763, 1957. 2. TC Bruice, SJ Benkovic. Bioorganic Mechanisms, Vol. II. Benjamin: New York, 1966, pp. 204–214. 3. GL Carlson, GM Brown. The natural occurrence, enzymatic formation, and biochemical signiﬁcance of a hydroxyethyl derivative of thiamine pyrophosphate. J Biol. Chem. 236:2099–2108, 1961. 4. LO Krampitz, G Gruell, CS Miller, KB Bicking, HR Skeggs, JM Sprague. An active acetaldehyde thiamine intermediate.
The question of which oxidizing agent is most suitable for hydroxyethyl-TDP revolves around the chemical nature of the group being oxidized and the anticipated chemical properties of the desired product, acetyl-TDP. The hydroxyethyl group in hydroxyethyl-TDP is the only alcoholic group in the molecule, so an oxidizing agent selective for alcohols would be the reagent of choice. Like the 2-acetyl-3,4-dimethylthiazolium ion, acetyl-TDP could be expected to be labile to hydroxide-catalyzed hydrolysis but would be stable in acidic solutions.
When used in acidic solutions, the acetyl-TDP produced is stable enough to be puriﬁed and characterized (14). Synthetic acetyl-TDP exists in aqueous solutions as a mixture of the three forms shown in Figure 5, a hydrate, the dehydrated acetyl form, and an internal adduct with the 4-amino group of the pyrimidine ring. This mixture was characterized by its 1H NMR spectrum, which showed three sets of resonances for the three forms (14). The equilibrium between the internally cyclized form and the dehyro form was pH dependent because of the ionization of the pyrimidine ring, and this pH dependence introduced a transition step in the pH rate proﬁle for hydrolysis.
Thiamine: Catalytic Mechanisms in Normal and Disease States (Oxidative Stress and Disease) by Mulchand S. Patel, Frank Jordan