O-酰基-L-丝氨酸衍生物和S-酰基-L-半胱氨酸衍生物的合成研究

Synthesis of O-acyl-L-serineand S-acyl-L-cysteine derivatives

目的寻找能将氨基酸侧链的羟基、巯基与二元羧酸连接成酯的方法。方法分别以L 丝氨酸和L 半胱氨酸为起始物 ,采用叔丁氧羰基、苄酯或二苯甲酯形式保护 ,分别与丁二酸单苄酯、草酸单苄酯、丁二酸单叔丁酯缩合成酯 ,合成了 3个未见文献报道的化合物O (4 苄氧丁二酰基 ) N 叔丁氧羰基 L 丝氨酸苄酯 (4 )、O (2 苄氧草酰基 ) N 叔丁氧羰基 L 丝氨酸苄酯 (8)、S (4 叔丁氧丁二酰基 ) N 叔丁氧羰基 L 半胱氨酸二苯甲酯 (12 )。化合物 4经氢解合成未见文献报道的化合物O 丁二酰基 N 叔丁氧羰基 L 丝氨酸 (5 )。化合物 5经酸解得到O 丁二酰基 L 丝氨酸(6)。结果与结论目标化合物的结构经光谱确证。通过这种方法二元羧酸能与氨基酸的羟基。

Aim To synthesize O acyl or S acyl amino acids by condensation of dicarboxylic acids and amino acids.Methods L serine and L cysteine were protected by Boc,Bn or Dpm,then condensed with succinic monoester,oxalyl monoester to produce the intermediates O (4 benzyloxysuccinyl) N Boc L serine benzyl ester (4), O (2 benzyloxyoxalyl) N Boc L serine benzyl ester (8), N Boc S (4 tert butoxysuccinyl) L cysteine diphenylmethyl ester (12).Compound 4 was converted into O succinnyl N Boc L serine (5)by hydrogenolysis,then into O succinnyl L serine (6) by acidolysis.Results Their structures were confirmed by the spectral detection.Conclusion Dicarboxylic acids can be esterified with OH or SH groups of amino acids by this innovative method.