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 |
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引用本文: | 洪丽虹,程艳丽,杜旭泽,张有来. 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[J]. 合成化学, 2016, 24(8): 713-716. DOI: 10.15952/j.cnki.cjsc.1005-1511.2016.08.16127 |
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作者姓名: | 洪丽虹 程艳丽 杜旭泽 张有来 |
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作者单位: | 天津理工大学 化学化工学院,天津 300384 |
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基金项目: | 国家自然科学基金资助项目(21303120);天津市自然科学基金资助项目(13JCYBJC42100);天津市“131”创新型人才培养工程第三层次;天津市高等学校大学生创新创业训练计划项目(201410060024) |
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摘 要: | 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。
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关 键 词: | 苯并噻喃 光控保护基 氨基酸 光反应 应用 |
收稿时间: | 2016-05-16 |
Application of A Novel Photolabile Protecting Group [2-(Diazomethyl)-3-phenyl-4H-thiochromen-4-one 1,1-dioxide] In Protection-photodeprotection of Amino Acids |
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Abstract: | 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{r[n(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 conditions[1a 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. |
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Keywords: | thiochromone S,S-dioxide photolabile protecting group amino acid photo-reaction ap-plication |
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