| Application of DEPBT on the Synthesis of the Protected Dipeptides Containing Histidine with Unprotected Imidazole Group by Solution Method |
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| 引用本文： | 沈鸿雁 田桂玲 朱文江 哈莎 叶蕴华. Application of DEPBT on the Synthesis of the Protected Dipeptides Containing Histidine with Unprotected Imidazole Group by Solution Method[J]. 中国化学, 2003, 21(7): 801-804. DOI: 10.1002/cjoc.20030210718 |
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| 作者姓名： | 沈鸿雁 田桂玲 朱文江 哈莎 叶蕴华 |
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| 作者单位： | KeyLaboratoryofBioorganicChemistryandMolecularEngineering,MinistryofEducation,CollegeofChemistryandMolecularEngineering,PekingUniversity,Beijing100871,China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China(No.20242006). |
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| 摘 要： | 3- (Diethoxyphosphoryloxy)- 1,2,3-benzotriazln-4 (3H)-one (DE-PBT) was an organophosphorus coupling reagent developed by our group. It was an effective coupling reagent for the synthesis of protected peptides containing Tyr, Ser and Thr with unprotected hydroxy group on their side chain. The further study of the synthesis of a series of protected dipeptides containing hisfidine with unprotected imidazole group using DEPBT is reported. During the synthetic procedure, the imidazole group of histidine did not need to be protected. When the carboxyl components were N-protected aromatic amino acids or basic amino acids, the yields were relatively high (63%--81%). However,when the carboxyl components were N-protected acidic amino acids, the yields were relatively low (47%--48%). The results expanded the application of DEPBT on the synthesis of bioactive peptides containing histidine.
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| 关 键 词： | DEPBT 应用 二肽 肽类 合成 缩二氨酸 组氨酸 咪唑 溶解方法 耦合试剂 缩氨酸 3－（二乙氧基磷酰基氧基）－1，2，3－苯并三唑精－4 （3H）－酮 |
Application of DEPBT on the Synthesis of the Protected Dipeptides Containing Histidine with Unprotected Imidazole Group by Solution Method |
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| SHEN,Hong-Yan TIAN,Gui-Ling ZHU,Wen-Jiang HA,ShaYE,Yun-HuaKey Laboratory of Bioorganic Chemistry and Molecular Engineering,Ministry of Education,College of Chemistry and Molecular Engineering,Peking University,Beijing ,China. Application of DEPBT on the Synthesis of the Protected Dipeptides Containing Histidine with Unprotected Imidazole Group by Solution Method[J]. Chinese Journal of Chemistry, 2003, 21(7): 801-804. DOI: 10.1002/cjoc.20030210718 |
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| Authors: | SHEN Hong-Yan TIAN Gui-Ling ZHU Wen-Jiang HA ShaYE Yun-HuaKey Laboratory of Bioorganic Chemistry Molecular Engineering Ministry of Education College of Chemistry Molecular Engineering Peking University Beijing China |
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| Affiliation: | SHEN,Hong-Yan TIAN,Gui-Ling ZHU,Wen-Jiang HA,ShaYE,Yun-HuaKey Laboratory of Bioorganic Chemistry and Molecular Engineering,Ministry of Education,College of Chemistry and Molecular Engineering,Peking University,Beijing 100871,China |
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| Abstract: | 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) was an organophosphorus coupling reagent developed by our group. It was an effective coupling reagent for the synthesis of protected peptides containing Tyr, Ser and Thr with unprotected hydroxy group on their side chain. The further study of the synthesis of a series of protected dipeptides containing histi-dine with unprotected imidazole group using DEPBT is reported. During the synthetic procedure, the imidazole group of his-tidine did not need to be protected. When the carboxyl components were N-protected aromatic amino acids or basic amino acids, the yields were relatively high (63%-81%). However, when the carboxyl components were N -protected acidic amino acids, the yields were relatively low (47%-48%). The results expanded the application of DEPBT on the synthesis of bioactive peptides containing histidine. |
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| Keywords: | DEPBT coupling reagent histidine peptide |
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