Enzymatic Synthesis Of Troxerutin Nitrogen-containing Derivatives

Troxerutin is one of flavonoid derivatives. with a number of similar activity groups.Clinically, as a widely used cardiovascular disease drug, selectively synthesize its derivativesfor developing pro-drug with new structure is important. Enzymes are highly efficientbiocatalysts. Enzymatic synthesis attracts attention because of its high selectivity andregioselectivity, mild condition and high efficiency which is applied in biology, organicsynthesis and other areas.In the thesis, the enzymes catalyzed regio-selective reaction of troxerutin with a series ofdivinyl dicarboxylates were studied. In pyridine, alkaline protease from Bacillus licheniformisselectively catalytic transesterification on primary hydroxyl of hydroxyethyl linked withbenzene ring in troxerutin. Succinyl, glutaryl, hexanedioyl, nonanedioyl, sebacoyl,tridecandioyl six different acyl chain length troxerutin vinyl esters were synthesized. Theproducts were characterized by¹H-NMR,¹³C-NMR, ESI-MS, FT-IR. Result showed thecorresponding troxerutin derivatives with monoacylation contain vinyl group.Troxerutin vinyl esters as substrate, Lipase LS-10catalyzed transesterification withpiperazine, corresponding products were characterized by¹H-NMR,¹³C-NMR, ESI-MS,FT-IR. The results show that vinyl ester group was substituted. Six different chain length oftroxerutin piperazine derivatives.were synthesized.Transesterification of troxerutin vinyl ester catalyzed by Lipase G Amano50lipase withmetformin, troxerutin triazine ring derivatives with different chain length were synthesized.By¹H-NMR,¹³C-NMR, ESI-MS, FT-IR. to characterize the structure of the products,indicating that new compounds forming a triazine ring containing the substituentsIn the thesis, influence factors on the yield and conversion of enzymatic synthesistroxerutin triazine ring derivatives such as enzyme source, enzyme concentration, reactiontime, solvent, substrate molar ratio, solvents, water content in solvent were investigated. Theresults showed that: the most suitable molar ratio is4/1, about1%water content of pyridineas solvent,50mg/mL of Lipase G Amano50as catalyst,50℃,108h, yield and conversionrate were stable, the reaction reached equilibrium.