A novel immonium type coupling reagent, 5-(1H-benzotria-zol-1-yloxy )-3,4-dihydro-1-methyl 2H-pyrrolium hexachlo-roantimonate (BDMP) has been designed, synthesized and u-tilized to synthesize oligopeptides and biologi...A novel immonium type coupling reagent, 5-(1H-benzotria-zol-1-yloxy )-3,4-dihydro-1-methyl 2H-pyrrolium hexachlo-roantimonate (BDMP) has been designed, synthesized and u-tilized to synthesize oligopeptides and biologically active pep-tide both in solution and solid phase with satisfactory yield, low racemization and fast reaction rate. The estimation of racemization and the influence of several reaction parameters were studied by HPLC method using the model reaction: Z-Gly-Phe-OH + Val-OMe·HCl→Z-Gly-D/L-Phe-Val-OMe. It was shown that the reactivity of BDMP was much higher and the racemization was much lower than those of HOBt-based 'onium' reagents, even though its analogues BOMI. To further verified the effectiveness of BDMP, Leu-enkephalin was synthesized both in solution and solid phase using BDMP as coupling reagent. The proposed mechanism was also speculated.展开更多
基金Project (No.9772045) supported by the National Natural Science Foundation of China.
文摘A novel immonium type coupling reagent, 5-(1H-benzotria-zol-1-yloxy )-3,4-dihydro-1-methyl 2H-pyrrolium hexachlo-roantimonate (BDMP) has been designed, synthesized and u-tilized to synthesize oligopeptides and biologically active pep-tide both in solution and solid phase with satisfactory yield, low racemization and fast reaction rate. The estimation of racemization and the influence of several reaction parameters were studied by HPLC method using the model reaction: Z-Gly-Phe-OH + Val-OMe·HCl→Z-Gly-D/L-Phe-Val-OMe. It was shown that the reactivity of BDMP was much higher and the racemization was much lower than those of HOBt-based 'onium' reagents, even though its analogues BOMI. To further verified the effectiveness of BDMP, Leu-enkephalin was synthesized both in solution and solid phase using BDMP as coupling reagent. The proposed mechanism was also speculated.
