化学学报 ›› 2001, Vol. 59 ›› Issue (10): 1740-1744. 上一篇    下一篇

研究论文

HOBt, HOOBt, HOSu与惰性氯代烷溶剂之间的反应及其对 多肽合成影响的研究

纪建国;张德仪;江军;叶蕴华;邢其毅   

  1. 北京大学化学与工程学院;北京大学生命有机与分子工程教育部重点实验室
  • 发布日期:2001-10-15

Studies on the reaction of HOBt, HOOBt, and HOSu with chloroalkane solvents and their affects on the peptide synthesis

Ji Jianguo;Zhang Deyi;Jiang Jun;Ye Yunhua;Xing Qiyi   

  • Published:2001-10-15

HOBt,HOSu,HOOBt是多肽合成中常用的试剂,它们常被用作羧基活化试剂和消旋抑制剂。首次发现HOBt,HOSu,HOOBt在碱的存在下可与氯代烷烃溶剂发生反应,并系统地研究了不同的反应条件对产率的影响和对多肽合成的影响。发现反应的产率与碱的用量,反应温度,反应物等因素有关,碱性越强,反应速度越快产率越高,HOBt较易反应,HOSu较为稳定,二氯甲烷易生成双取代产物,1,2-二氯乙烷易生成单代产物,所有产物均经硅胶柱层析分离纯化,共合成8个经合物并通过光谱鉴定。虽然在模型二肽BocAlaPheOCH3合成反应中检测到少量副产物的产生,但二肽的产率>82%。

关键词: 羟基苯并三氮唑, 三嗪P, 羟基琥珀酰亚胺, 氯代烃, 多肽, 溶剂

HOBt, HOSu and HOOBt are the widely used reagents in the peptide synthesis, they are used as the activitor of carboxyl group and the inhibitor of racemization. HOBt, HOSu and HOOBt were found for the first time that they could react whith chloroalkane solvents in the presence of different base. The yields were realted to the reaction condition such as the quantity and variety of bases, reaction temperature and the structure of the reactants. The more of the bases used, the higher of the yield and reacton speed. HOBt is more active than HOSu, CH2Cl2 is easy to form disubstituted proucts, ClCH2CH2Cl is easy to form monosubstituted products. All of the products were purified by chromatography on silica-gel, eight new compounds were identified by MS and 1^H NMR. In the model synthesis of dipeptide BocAlaPheOCH3, the by-product was detected and the yield of the dipeptide was over 82%。

Key words: TRIAZINE P, CHLOROHYDROCARBON, POLYPEPTIDE, SOLVENTS

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