A facile method for vancomycin C-terminus functionalization and derivatization through hydrazide

doi:10.1016/j.bmcl.2021.128027

	A facile method for vancomycin C-terminus functionalization and derivatization through hydrazide
	Hu, Yu 1,2; Zou, Xiangman 2,3; Shi, Weiwei 2,4; Ma, Chenhui 2,4; Chen, Feifei 2; Li, Jian 2,4; Jiao, Shang 2,4; Pan, Guoyu 2,4; Lan, Lefu 2,4; Huang, Wei 2,4,5
刊名	BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
	2021-06-15
卷号	42 页码:6
关键词	Vancomycin C-terminus modification Hydrazide derivatives Native Chemical Ligation Antibacterial activity
ISSN号	0960-894X
DOI	10.1016/j.bmcl.2021.128027
通讯作者	Tang, Feng(tangfeng2013@simm.ac.cn) ; Zhang, Fan(zhangfan830720@163.com)
英文摘要	Over 60-year clinical use of vancomycin led to the emergence of vancomycin-resistant bacteria and threatened our health. To combat vancomycin-resistant strains, numerous vancomycin analogues were developed, such as Telavancin, Oritavancin and Dalbavancin. Extra structures embedded on C-terminus has been proved to be an effective strategy to promote antibacterial activity of vancomycin against vancomycin-resistant strains. Here, we reported a facile strategy, inspired by native chemical ligation, for vancomycin C-terminus functionalization and derivatization. The introduction of C-terminal hydrazide on vancomycin not only provided us an accessible method for C-terminus functionalization through carbonyl azide and thioester, also acted as an efficient site for vancomycin structure modifications. Based on hydrazide-vancomycin, we effectively conjugated cysteine and cysteine containing peptides onto vancomycin C-terminus, and two fluorescent FITC-vancomycin were prepared through Cys-Maleimide conjugation. Meanwhile, we introduced lipophilic structures onto vancomycin C-terminus via the hydrazide moiety. The obtained vancomycin derivatives were evaluated against both Grampositive and negative bacteria strains.
资助项目	National Natural Science Foundation of China (NNSFC)[21877116] ; SIMM institute fund[CASIMM0120202009] ; Shanghai Action Plan of Technological Innovation[18431900700] ; National Megaproject for Innovative Drugs[2019ZX09721001004009]
WOS关键词	CHEMICAL-SYNTHESIS ; RESISTANT ; LIGATION ; PROTEINS ; STRATEGY ; ANALOGS
WOS研究方向	Pharmacology & Pharmacy ; Chemistry
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000655255700014
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/297038]
专题	中国科学院上海药物研究所
通讯作者	Tang, Feng; Zhang, Fan
作者单位	1.Jinzhou Med Univ, Sch Pharm, Jinzhou 121001, Peoples R China 2.Chinese Acad Sci, Ctr Biotherapeut Discovery Res, Shanghai Inst Mat Med, CAS Key Lab Receptor Res,CAS Ctr Excellence Mol C, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China 3.Univ South China, Hunan Prov Cooperat Innovat Ctr Mol Target New Dr, Inst Pharm & Pharmacol, Hunan Prov Key Lab Tumor Microenvironm Respons Dr, Hengyang 421001, Hunan, Peoples R China 4.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China 5.Univ Chinese Acad Sci, Sch Pharmaceut Sci & Technol, Inst Adv Study, Hangzhou 310024, Peoples R China
推荐引用方式 GB/T 7714	Hu, Yu,Zou, Xiangman,Shi, Weiwei,et al. A facile method for vancomycin C-terminus functionalization and derivatization through hydrazide[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2021,42:6.
APA	Hu, Yu.,Zou, Xiangman.,Shi, Weiwei.,Ma, Chenhui.,Chen, Feifei.,...&Zhang, Fan.(2021).A facile method for vancomycin C-terminus functionalization and derivatization through hydrazide.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,42,6.
MLA	Hu, Yu,et al."A facile method for vancomycin C-terminus functionalization and derivatization through hydrazide".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 42(2021):6.