Study On Chiral Amplification Of L-tryptophan In Theory And Experiment And The Synthesis Of ?-lactams With Novel Structures

A new method about the chiral amplification of L-amino acids by using chemical reactions was proposed in the study.Tryptophan was regarded as the main research object.Due to the poor solubility of tryptophan in organic solvents,tryptophan was converted to corresponding tryptophan methyl ester first.Next,the reaction of tryptophan methyl ester and diacetyl was used as model reaction to study chiral amplification of L-tryptophan,and then the conclusion was drawn that the process of chiral amplification is inevitable.And with the value of%ee₁?enantiomeric excess of L-tryptophane methyl ester before the reaction?increasing,the difference between%ee₂?enantiomeric excess of L-tryptophane methyl ester after the reaction?and%ee₁ will increase first and decrease next,however,the value of%ee₂/%ee₁ will decrease.Besides,the simulation experiment for chiral amplification of L-tryptophan in nature was conducted twice.5 g and 11.5 g of L-tryptophan methyl ester with%ee₁of 0.7%¹.0%were used as the starting materials and reacted twice with diacetyl,and about 90%of materials were consumed each time.The%ee₂ increased to 2.7%³.2%and 3.0%³.4%,respectively.The paper studied the chiral amplification of L-tryptophane in theory and experiment,which provided new research idea and method for the related studies.Besides,the reaction of phenylalanine methyl ester and oxalyl chloride was used as model reaction to study chiral amplification of L-phenylalanine,which further confirms the conclusions above.In the process of exploring the model reaction of chiral amplification of L-phenylalanine,the paper found that L-phenylalanine methyl ester reacted with?-phthalaldehyde resulting in new?-lactams.Some other L-amino acid methyl esters and L-amino alcohols were used as substrates to verify this reaction.All the?-lactams obtained above were used for anti-cancer activity study,however,the anti-cancer activity of this type of?-lactams was not good as expected,IC₅₀>40?M.