新型光控保护基(2-重氮基-3-苯基-4H-磺酰基苯并噻喃)在氨基酸保护-光控脱保护反应中的应用

将新型磷酸基光控保护基(2-重氮基-3-苯基-4H-磺酰基苯并噻喃,PPG)应用于氨基酸［甘氨酸(1a), L 丙氨酸(1b), L 苯丙氨酸(1c)和L-脯氨酸(1d)］的保护 光控脱保护反应。产物结构经¹H NMR, ¹³C NMR和HR-FAB MS表征。研究了物料比r［n(PPG) : n(1a)］,催化剂和反应温度对2a收率的影响。结果表明：在最佳反应条件［1a 0.1 mmol, r=1.25,于室温反应65 h］下，2a收率80%。FL监测光控脱保护反应表明：反应在15 min内完成。

Application of A Novel Photolabile Protecting Group [2-(Diazomethyl)-3-phenyl-4H-thiochromen-4-one 1,1-dioxide] In Protection-photodeprotection of Amino Acids

A novel photolabile protecting group, 2-( diazomethyl)-3-phenyl-4H-thiochromen-4-one 1, 1-dioxide( PPG) , was applied to the protection and photodeprotection of amino acids, including gly-cine(1a), L-alanine(1b), L-phenylalanine(1c) and L-proline(1d).The structures were character-ized by 1H NMR, 13C NMR and HR-FAB-MS.Effect of mole ratio{rn(PPG)∶n(1a)]}, catalyst and reaction temperature on yield of 2a were investigated.The results indicated that yield of 2a was 80%under the optimum conditions1a 0.1 mmol, r=1.25, reaction at rt for 65 h].The photodepro-tection, which was detected by FL, completed in less than 15 min.