Synthesis of Fmoc-Thr Unit Carrying Core 1 O-Linked Sugar With Acid-Sensitive O-Protecting Group and Its Application to the Synthesis of Glycosylated Peptide Thioester

被引：11

作者：

Asahina, Yuya ^{[1
]}

Fujimoto, Rina ^{[2
]}

Suzuki, Akemi ^{[3
]}

Hojo, Hironobu ^{[1
]}

机构：

[1] Osaka Univ, Inst Prot Res, Suita, Osaka 5650871, Japan

[2] Tokai Univ, Dept Appl Biochem, Hiratsuka, Kanagawa 2591292, Japan

[3] Tokai Univ, Inst Glycosci, Hiratsuka, Kanagawa 2591292, Japan

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2015年 / 34卷 / 01期

关键词：

Core; 1; sugar; N-alkylcysteine; Peptide thioester; Acid-sensitive protecting group; O-glycoprotein; SOLID-PHASE SYNTHESIS; CHEMOENZYMATIC SYNTHESIS; ASSISTED THIOESTERIFICATION; GLYCOPEPTIDE; GLYCAN; SEGMENT; GLYCOPROTEIN;

D O I：

10.1080/07328303.2014.977909

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We newly designed and synthesized a 9-fluorenylmethoxycarbonyl (Fmoc)-threonine unit carrying the core 1 O-glycan, which is protected by the 4-methylbenzyl (MBn) group. This protection tactic enabled not only efficient assembly of glycoamino acid derivatives but also one-step deprotection by trifluoroacetic acid (TFA) after the Fmoc-solid-phase peptide synthesis (SPPS). The usefulness of this unit was demonstrated by the Fmoc-SPPS of peptide thioester using the N-alkylcysteine (NAC)-assisted thioesterification method. The human interleukin-2 (1-27) sequence was assembled on the NAC resin and the obtained resin was treated with TFA containing cation scavengers to achieve one-step deprotection. The crude peptide was then thioesterified by reacting with an arylthiol to successfully obtain the desired peptide thioester carrying the core 1 O-glycan.

引用

页码：12 / 27

页数：16