3-N^ε-苄氧羰基赖氨酰基-吗啉-2，5-二酮的合成研究

Synthesis and Characterization of Inexpensive 3-N^ε-Benzyloxycarbonyl-L-Lysyl-Morpholine- 2,5-Dione

以L-赖氨酸(L-Lysine)为原料合成了氨基酸类环化物单体——3-Nε-苄氧羰基赖氨酰基-吗啉-2,5-二酮。反应过程包括对ε-氨基的保护、乙酰化反应、分子内环化缩合反应。选择苄氧羰酰基(z)为ε-氨基的保护基团;三乙胺用作反应副产物溴化氢的中和剂。运用红外光谱(IR)、差示扫描量热法(DSC)、核磁共振(NMR)和元素分析等方法对产物的结构和性能进行了表征。通过分析测试证实了合成产物为3-Nε-苄氧羰基赖氨酰基-吗啉-2,5-二酮,产物熔点为254.5℃,构型为立体异构环状结构。

Purpose. We will call 3-N^ε-benzyloxycarbonyl-L-lysyl-morpholine-2,5-dione ＂compound＂. The starting material used abroad is expensive and the yield is low （16%～28%）; furthermore, to our best knowledge, no characterization of ＂compound＂ is available in the open literature. We now use low-cost L- lysine as starting material, succeed in raising the yield of ＂compound＂ to about 66 %, and characterize it. In the synthesis of ＂compound＂, the reactive processes used by us included the protection of amino group of lysine, acetylation, and intramolecular cyclizative condensation reaction. The benzoxycarbonyl chloride was selected as amino group protection agent, and the yield was elevated by replacing sodium bicarbonate with triethyl amide as the acid＇s neutralizer. The resulting material or ＂compound＂ was cyclizative; its structure and properties were characterized by IR, DSC, NMR and elemental analysis. The results of characterization show that： （1） ＂compound＂ has a chiral carbons next to the carbonyl group, so the formation of the ring structure is not stereospecific; （2） the melting point is about 254.5℃. ＂Compound＇s＇＇ homopolymer and copolymers with lactide or caprolactone have reaction-active groups and excellent biocompatibility and biodegradability; so they can be used in tissue engineering and as controlled-drugrelease carriers.