EurekaMag
+ Translate
+ Most Popular
Cranial nerves of Labeo rohita (Ham.)
Cytogenetic analysis of ZZWW triploid silkworm (Bombyx mori)
Effectiveness of posterior crossbite correction during the mixed dentition
Classification of liver cirrhosis based on parenchymal echo patterns and its clinical usefulness for diagnosis of liver cirrhosis
The identity of the lipstick mold of cultivated mushrooms agaricus bisporus
Inhibition of haemolytic activity of snake and scorpion venom by date extract
Effectiveness of iron amino acid chelate on the treatment of iron deficiency anemia in adolescents
Furunculosis and pseudofurunculosis
Some Biological Applications of Organometallic Compounds
Stassanisation of Milk
Pulse rate, respiration, and body temperature of Philippine carabaos
Sports fans: measuring degree of identification with their team
Enterobacter amnigenus. An unusual human pathogen
Vitamin B12 deficiency as a worldwide problem
Therapy for acne with saccharomyces boulardii
Comparison of rice bran and maize bran as feeds for growing and fattening pigs
The Difil Test kit for detection of canine heartworm microfilariae
Gafner Mini-skidder
Vegetable protein for combating protein malnutrition in developing countries
Comparative morphology of fish olfactory epithelium part 6 siluriformes
Mycotechnology: the role of fungi in biotechnology
On the nature and role of vivotoxins in plant disease
A study on compatibility of some insecticides with a fungicide on small cardamom (Elettaria cardamomum Maton.)
Evidence for Late Cretaceous N-S dextral shear in the west-central crystalline core, North Cascades, Washington
Advantages and disadvantages of bordeaux mixture and of lime-sulphur used on apples in the growing season

Synthesis and crystal structure of an analog of 2 alpha lactyl thiamin racemic methyl 2 hydroxy 2 2 thiamin ethyl phosphonate chloride tri hydrate a conformation for a least motion maximum overlap mechanism for thiamin catalysis


Synthesis and crystal structure of an analog of 2 alpha lactyl thiamin racemic methyl 2 hydroxy 2 2 thiamin ethyl phosphonate chloride tri hydrate a conformation for a least motion maximum overlap mechanism for thiamin catalysis



Journal of the American Chemical Society 104(11): 3089-3095



ISSN/ISBN: 0002-7863

Methyl 2-hydroxy-2-(2-thiamin)ethylphosphonate, phiosphalactylthiamin, is a phosphonate analogue of 2-(1-carboxy-1-hydroxyethyl)thiamin, the initial intermediate in the thiamin-catalyzed decarboxylation of pyruvic acid. Crystal-structure analysis of phosphalactylthiamin reveals that the thiamin portion of the molecule assumes the S conformation that is characteristic of other C(2)-substituted thiamins. However, in contrast to previously studied derivatives the conformation of the phosphalactyl substituent is unique in that its hydroxyl is in close contact with the bridging methylene instead of the thiazolium ring S and the bond to the phosphonate is oriented perpendicular to the ring plane. This structural feature is also consistent with the NMr spectrum. The structure suggests that the principles of least motion and maximum orbital overlap can be applied to thiamin catalysis of the decarboxylation of pyruvate since the observed structure conforms to theoretical expectations for 2-(.alpha.-lactyl)thiamin diphosphate.

Please choose payment method:






(PDF emailed within 1 workday: $29.90)

Accession: 006561981

Download citation: RISBibTeXText

Related references

Snapshot of a key intermediate in enzymatic thiamin catalysis: crystal structure of the alpha-carbanion of (alpha,beta-dihydroxyethyl)-thiamin diphosphate in the active site of transketolase from Saccharomyces cerevisiae. Proceedings of the National Academy of Sciences of the United States of America 99(2): 591-595, 2002

Effects of treatment with thiamin antagonists, oxythiamin and pyrithiamin and of thiamin excess of the levels and distribution of thiamin in rat tissues. Journal of Nutritional Science and Vitaminology 28(3): 217-224, 1982

Snapshot of a key intermediate in enzymatic thiamin catalysis: crystal structure of the a-carbanion of (a,b-dihydroxyethyl)-thiamin diphosphate in the active site of transketolase from Saccharomyces cerevisiae. Proceedings of the National Academy of Sciences of the United States of America 99(2): 1-5, 2002

Chemical behavior of isolated thiamin ylide in neutral aqueous solution a new mechanism of interconversion of thiamin and thiamin thiolate. Heterocycles 26(1): 13-18, 1987

Thiamin catalysis 2. kinetics and mechanism of the generation of the yellow form of thiamin. Journal of the American Chemical Society 104(5): 1341-1344, 1982

Crystal structure of thiamin methyl acetyl-phosphonate. Acta Crystallographica Section A Foundations of Crystallography 37(A1): C77-C77, 1981

On the mechanism of action of thiamin enzymes, Crystal structure of 2-(α-hydroxyethyl)thiamin pyrophosphate (HETPP). Complexes of HETPP with zinc(II) and cadmium(II). Jbic Journal of Biological Inorganic Chemistry 3(5): 437-448, 1998

Carbon 13 magnetic resonance studies of DL-2-(alpha-hydroxyethyl) thiamin and related compounds. Relation of kinetic acidity to electronic factors in thiamin catalysis. Journal of Biological Chemistry 251(9): 2564-2570, 1976

Blood thiamin and thiamin phosphate esters in patients with alcohol dependence syndrome before and 24 hrs after thiamin injection. Clinical Nutrition (Edinburgh) 10(SPEC Suppl 2): 23, 1991

Nervous tissue thiamin metabolism in vivo 1. transport of thiamin and thiamin mono phosphate from plasma to different brain regions of the rat. Brain Research 293(2): 319-328, 1984

Blood and serum thiamin and thiamin phosphate esters concentrations in patients with alcohol dependence syndrome before and after thiamin treatment. Alcoholism Clinical and Experimental Research 16(2): 320-325, 1992

Dietary thiamin supply during lactation influences thiamin status in lactating rats and their offspring and the thiamin level in milk. Zeitschrift für Ernahrungswissenschaft 36(2): 169-175, 1997

Blood and serum thiamin and thiamin phosphate esters concentrations in patients with alcohol dependence syndrom before and after thiamin treatment. Alcoholism, Clinical and Experimental Research 16(2): 320-325, 1992

Behaviour of thiamin and its phosphate esters in thiamin deficiency in isolated rat liver perfused with thiamin. Arch. Sci. biol 53: 58-72, 1969

Intestinal thiamin transport in rats. Thiamin and thiamin phosphoester content in the tissue and serosal fluid of everted jejunal sacs. Pflugers Archiv: European Journal of Physiology 393(1): 37-41, 1982