N-Methylated tetrapeptide synthesis via sequential filtration procedures based on Teflon™ immobilization utilizing the properties of fluorous 9-fluorenylmethyl ester

被引：1

作者：

Ishihara, Kotaro ^{[1
]}

Tanaka, Yota ^{[1
]}

Kato, Yamato ^{[1
]}

Ishihara, Kazuki ^{[1
]}

Ieda, Nodoka ^{[1
]}

Mizuno, Sakura ^{[1
]}

Hagiwara, Yuna ^{[1
]}

Nagaya, Akihiro ^{[2
]}

Nagatsuka, Takayuki ^{[2
]}

Shioiri, Takayuki ^{[1
]}

Matsugi, Masato ^{[1
]}

机构：

[1] Meijo Univ, Fac Agr, 1-501 Shiogamaguchi,Tempaku, Nagoya 4688502, Japan

[2] Nissan Chem Corp, 5-1,Nihonbashi 2 Chome,Chuo Ku, Tokyo 1036119, Japan

来源：

TETRAHEDRON LETTERS | 2023年 / 124卷

关键词：

N -methyl peptides; Fluorous; Protecting group; Purification; MIXTURE SYNTHESIS; FMOC REAGENTS; PURIFICATION; PEPTIDES; CATALYST;

D O I：

10.1016/j.tetlet.2023.154606

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and convenient TeflonTM-based method for N-methyltetrapeptide purification relying on fluorous 9-fluorenylmethanol as a C-terminal protecting group was developed. Fluorous compound- protected peptides supported on TeflonTM powder could be easily transferred between the fluorous solid phase (TeflonTM) and the liquid phase (reaction solution) by tuning the hydrophobicity of the solvent. Fluorous peptides present in a homogeneous state in solution during each elongation reaction were immobilized on TeflonTM at the end of each reaction by adjusting the hydrophobicity of the reaction solution, and they could be isolated by simple filtration, affording the facile synthesis of the correspond-ing N-methylated tetrapeptide. & COPY; 2023 Elsevier Ltd. All rights reserved.

引用

页数：4