使用Nin-(2,4,6-三异丙基苯磺酰基)色氨酸对两种含脑啡肽的肽（肽E和强啡肽(1-24)）进行溶液合成。

Solution syntheses of two enkephalin-containing peptides, peptide E and dynorphin(1-24), using Nin-(2,4,6-triisopropylphenylsulfonyl)tryptophan.

作者信息

Kitagawa K, Kawamoto T, Futaki S, Kiyama S, Akita T, Moritoki H, Kiso Y

出版信息

Chem Pharm Bull (Tokyo). 1989 Oct;37(10):2631-8. doi: 10.1248/cpb.37.2631.

DOI:10.1248/cpb.37.2631

Abstract

Two enkephalin-containing peptides, peptide E and dynorphin(1-24), were synthesized by conventional solution methods employing a new Trp derivative, Nin-(2,4,6-triisopropylphenylsulfonyl)tryptophan [Trp(Tps)]. All protecting groups employed including the Tps group were removed by treatment with 1 M trifluoromethanesulfonic acid (TFMSA)-thioanisole in trifluoroacetic acid (TFA) at the final steps of these syntheses. Subsequent purifications by Sephadex G-25 chromatography, CM-Biogel A ion exchange chromatography, and reversed-phase high-performance liquid chromatography afforded highly purified samples. Both synthetic peptide E and dynorphin(1-24) exhibited high in vitro opioid activity. The usefulness of this new tryptophan derivative for practical peptide synthesis was established through these syntheses of complex Trp-containing peptides.

摘要

采用一种新的色氨酸衍生物Nin-(2,4,6-三异丙基苯磺酰基)色氨酸[Trp(Tps)]，通过传统溶液法合成了两种含脑啡肽的肽，即肽E和强啡肽(1-24)。在这些合成的最后步骤中，通过用1 M三氟甲磺酸(TFMSA)-硫代苯甲醚在三氟乙酸(TFA)中处理，除去了包括Tps基团在内的所有保护基团。随后通过Sephadex G-25柱色谱、CM-生物凝胶A离子交换色谱和反相高效液相色谱进行纯化，得到了高纯度的样品。合成的肽E和强啡肽(1-24)在体外均表现出高阿片样活性。通过这些复杂含色氨酸肽的合成，证实了这种新的色氨酸衍生物在实际肽合成中的实用性。