N-(1-萘甲基)-甘氨酰丝氨酸甲酯的合成

Synthesis of N-( 1-menaphthyl)-glycyl-serine Methyl Ester

芳环与肽是人工核酸酶设计中非常重要的两个结构片段,本文报道了一种用亚甲基连接刚性大环结构与小肽的方法,主要以甘氨酸﹑丝氨酸和萘甲醛为原料,通过还原氨化、氨基保护、缩合、脱保护等反应合成了N-(1-萘甲基)-甘氨酰丝氨酸甲酯,文中设计了两条合成路线,并比较了二者的优缺点。中间体结构用1HNMR进行鉴定,目标化合物结构用1HNMR,MASS,HRMS和HPLC进行了表征。

Aromatic ring and peptide are two important structural fragments in the design of artificial nuclease. A method of using methylene to link rigid ring structure with small peptide was reported. N-（ 1-menaphthyl）-glycyl-serine methyl ester was synthesized by using glycine, serine and 1- naphthaldehyde as start materials through reductive amination, amino protection, condensation and deprotection reaction. Two designed synthetic routes were investigated for their advantages and disadvantages. The intermediates were identified by ^1HNMR and title compound were further characterized by MASS, HRMS and HPLC.