一种合成脱氢肽的新方法

• 作 者: 龙康侯 简志刚 钟世舟
• 机 构: 中山大学化学系,中山大学化学系,中山大学测试中心,
• 出 处: 中山大学学报(自然科学版)
• 发表日期: 1987年04期
• 关键词: 脱氢 α-氨基酸 脱氢肽 脱氢氨基酸 质子酸 (口恶)唑啉 四氯化碳 合成 三苯基膦 三苯基

由N端保护的氨基酸或肽与β-羟基-α-氨基酸酯在三苯基膦、三乙胺、四氯化碳的存在下直接缩合,一步就可得到C端含脱氢氨基酸的肽类.在L-苏氨酸甲酯的情况下,全部生成Z型脱氢氨基酸.其可能的反应历程是N端保护的氨基酸或肽与β-羟基-α-氨基酸酯首先缩合形成肽键,然后进一步脱水生成产物.当用同样试剂处理Boc-L-ILe-L-Ser-L-ILe-OMe时,则形成肽类噁唑啉.影响反应方向的主要因素是α—C—H键质子酸性和酰胺N—H键质子酸性的相对强弱.

The N-terminal protected amino acid or peptide is directly condensed with the β-hydroxy-α-amino acid ester in the presence of triphenylphosphine, triethylamine and carbon tetrachloride to obtain the C-terminal dehydrogenated amino acid-containing peptide In the case of L-threonine methyl ester, Z-dehydroamino acids are all formed.The possible reaction is that the N-terminal protected amino acid or peptide is first condensed with the β-hydroxy-α-amino acid ester to form a peptide bond and then The product was further dehydrated to form the peptide oxazoline when Boc-L-ILe-L-Ser-L-ILe-OMe was treated with the same reagent.The main factors affecting the reaction direction were proton acid And amide N-H proton proton relative strength.