Optimal peptide hydrazide ligation with C-terminus Asp, Asn, and Gln hydrazides

doi:10.1016/j.tetlet.2016.07.101

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	Optimal peptide hydrazide ligation with C-terminus Asp, Asn, and Gln hydrazides
	Tian, Xiaobo 1,2; Li, Jie 2; Huang, Wei 2
刊名	TETRAHEDRON LETTERS
	2016-09-21
卷号	57 期号:38 页码:4264-4267
关键词	Peptide hydrazide ligation C-terminus cyclization CTC-resin
ISSN号	0040-4039
DOI	10.1016/j.tetlet.2016.07.101
文献子类	Article
英文摘要	Peptide hydrazide ligation is a newly reported approach using C-terminus hydrazide as the precursor of thioester for ligation with N-terminus Cys-peptides. However, peptide hydrazides with C-terminus Asp, Asn, and Gln are difficult to generate because of cyclization side reaction happened during peptide cleavage from Wang resin. To prevent the cyclization, we chose the acid-sensitive CTC-resin as the support and utilized two-step cleavage strategy: (1) release the peptide hydrazide bearing side-chain protection from the support with 1% TFA; (2) remove the side-chain protection with 90% TFA to give the corresponding peptide hydrazides. Peptide ligation using, these hydrazides with a Cys-peptide indicated the high efficiency in peptide elongation. The current study expands the scope of the peptide hydrazide ligation to all 20 natural amino acids at C-terminal. (C) 2016 Elsevier Ltd. All rights reserved.
资助项目	National Natural Science Foundation of China (NNSFC)[21372238] ; National Natural Science Foundation of China (NNSFC)[21572244] ; SIMM institute fund[CASIMM0120153004]
WOS关键词	NATIVE CHEMICAL LIGATION ; SOLID-PHASE SYNTHESIS ; PROTEINS ; THIOESTERS ; CHEMISTRY ; MECHANISM ; SURROGATE
WOS研究方向	Chemistry
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000383313900002
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/275886]
专题	生物技术药物研发中心（筹）药物安全性评价中心
通讯作者	Tian, Xiaobo; Huang, Wei
作者单位	1.Nanchang Univ, Coll Pharm, 461 Bayi Rd, Nanchang 330006, Peoples R China; 2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Ctr Excellence Mol Cell Sci, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Tian, Xiaobo,Li, Jie,Huang, Wei. Optimal peptide hydrazide ligation with C-terminus Asp, Asn, and Gln hydrazides[J]. TETRAHEDRON LETTERS,2016,57(38):4264-4267.
APA	Tian, Xiaobo,Li, Jie,&Huang, Wei.(2016).Optimal peptide hydrazide ligation with C-terminus Asp, Asn, and Gln hydrazides.TETRAHEDRON LETTERS,57(38),4264-4267.
MLA	Tian, Xiaobo,et al."Optimal peptide hydrazide ligation with C-terminus Asp, Asn, and Gln hydrazides".TETRAHEDRON LETTERS 57.38(2016):4264-4267.