Air N-protection free ligation of the peptide thioester and the peptide with an N-alkoxy- or N-aryloxyamino group at its N-terminus

被引：3

作者：

Hojo, Hironobu ^{[1
]}

Kawakami, Toru ^{[1
]}

Hiroyama, Yuta ^{[2
]}

Aimoto, Saburo ^{[1
]}

机构：

[1] Osaka Univ, Inst Prot Res, 3-2 Yamadaoka, Suita, Osaka 5650871, Japan

[2] Hamari Chem Ltd, Higashi Yodogawa Ku, 1-4-29 Kunijima, Osaka 5330024, Japan

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 49期

关键词：

Peptide thioester; Ligation method; N-Methoxy group; Samarium(II) iodide reduction; Atrial natriuretic peptide; NATIVE CHEMICAL LIGATION; ONE-POT LIGATION; CHEMOENZYMATIC SYNTHESIS; POLYPEPTIDE-SYNTHESIS; COPPER(II) CHLORIDE; O BONDS; PROTEINS; DESULFURIZATION; CYSTEINE; CLEAVAGE;

D O I：

10.1016/j.tetlet.2017.10.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Peptides with an N-alkoxy or N-aryloxy amino acid at their N-terminus were synthesized and successfully ligated with a peptide thioester by silver ion activation under a slightly acidic condition without requiring protection of the side chain amino groups. The N-methoxy group was easily cleaved by the SmI2 reduction in CH3OH aq. to obtain the desired peptide with a native peptide bond. This method was successfully applied to the synthesis of the human atrial natriuretic peptide showing the efficiency of the novel ligation. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：4638 / 4641

页数：4

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