Research Of Tetrahydrofolate Coenzyme Model's Synthesis And Function

In the living bodies, the most chemical reactions are finished by enzymes, enzymes is activity, selectivity and efficiency for the chemical reactions in the living body as catalysts. Tetrahydrofolate coenzyme is responsible for transfer of one-carbon fragment in the biological synthesis and metabolism and supplies methyl for all kinds of compounds. It is very valuable to supplied science in organic synthesis and medicine for us synthesizing new model compound which are analogous with structure of tetrahydrofolate coenzyme by organic synthesis methods and imitating one-carbon unit transfer reaction with new model compound in laboratory.When transferring one-carbon unit, it is finished by three levels of oxidation: methanol, formaldehyde and formic acid. In order to supplying the reaction of living body to organic synthesis, we designed and synthesized two formic acid level model compounds of the tetrahydrofolate coenzyme: 1-methyl-2-ethyl-3-(p-methoxyben esulfonyl)imidazolinium iodide 28and 1-methyl-2-isobuthyl-3-(p-methylbenesulfon-yl)imidazolinium iodide 53on the structure and reaction mechanism of the tetrahydrofolate coenzyme. But we researched detailedly the model compound 28 in hydrolysis , reduction and one-carbon transfer. The research content were as follow:1. model compound 28 can hydrolyze in the dilute sodium hydroxide solution, forming the derivative of ethylene dimine. This reaction process imitated hydrolysis mechanism of the tetrahydrofolate coenzyme. The model compound 28was returned to N-methyl-N-propyl-N'-(p- methoxy)benzenesulfonyl ethyldiamine with sodiumborohydride.2. Imitating the reaction of the tetrahydrofolate coenzyme's formic acid level one-carbon tra-nsfer: The reaction of 28 with monofunctional nucleophiles: malononitrile, nitromethane, ethyl malonate,aniline,p-toluidine,p-methoxyaniline,p-chloroaniline,4-aminocyclohexanol,pyridine-3-amine, piperidin-4-ol, lead to compounds 34,35,36,37,38,39,40,41,42,43,44 of formic acid level three-carbon portion transfer .Reaction of 28 ,53with bifunctional Nucleophiles: o-phenylenediamine, 2-aminophenol, achieve three-carbon unit whole transfer and give compounds 45,46,54,55.3. Imitating the reaction of the tetrahydrofolate coenzyme's formaldehyde level one-carbon transfer: Reactions of 28 with malo nonitrile, nitromethane, ethyl malonate, lead to three formaldehyd-elevel model compounds 34, 35, 36 respectively. Reactions of 35 with tryptamine, pepper peptamine, bring about formaldehyde level substituted three-carbon unit transfer and form functionalized tetrahydro-B-carboline derivatitives 48,49.The above research results proved that we imitated effectively tetrahydrofolate coenzyme'function of substituted one-carbon unit transfer and achieved substituted many-carbon unit transfer. At the same time, showed that synthesized model compounds not only possess the function of tetrahydrofolate coenzyme transferring one-carbon unit, but also the function of transferring many-carbon unit . The re-search on imitating tetrahydrofolate coenzyme's natural can supply a new approach for organic synthesis and fundamental theory for understandine of the effected mechanism of the living thing material in the body. In the total research, this paper has formed 20 new compounds and their structures have been identified by 1HNMR, IR, EA, MS.