Journal of Organic Chemistry p. 3712 - 3718 (1981)
Update date:2022-08-04
Topics:
Bergeron, Raymond J.
Burton, Philip S.
Kline, Steven J.
McGovern, Kathy Ann
A biomimetic approach to the synthesis of N4-acylated N1,N8-bis(2,3-dihydroxybenzoyl)spermidine siderophores is described.The key to the sequence is the use of Cu(II) as a transitory protecting group for the catechols of N1,N8-bis(2,3-dihydroxybenzoyl)spermidine in the condensation of this synthon with the model acylating agent N-(2-hydroxybenzoyl)glycine.An alternative route to this siderophore analogue employing classical methods is offered as proof of structure.Preliminary investigations aimed at characterizing the chelate of interest are also described.Proton NMR paramagnetic line broadening studies confirm the catechols of N1,N8-bis(2,3-dihydroxybenzoyl)spermidine to be the chelating functionality.The stoichiometry of the complex is determined by spectrophotometric methods while the cumulative formation constants of the various protonated species are established by potentiometric techniques.
View MoreJiangXi Keyuan Biopharma Co., LTD.
Contact:+86-563-6833666
Address:Guangde Fine Chemical Zone, Anhui Province, China
Xi'an Tizan Tech & Industry Co., Ltd.
Contact:86-18629066522
Address:C3009 TANG FENG INTERNATIONAL PLAZA, NO.18 FENGHUI NAN ROAD, XI'AN HIGH TECH ZONE, 710075 CHINA.
Tianjin Pharmacn Medical Technology Co.,Ltd.
Contact:86-22-60122566ext.866(English),23359620
Address:Green Industrial Base, 6 Haitaifazhan Sixth Rd., Huayuan Industrial Area, Tianjin, 300384, China
Wuhan Silworld Chemical Co.,Ltd
website:http://www.silworldchemical.com
Contact:+86-27-85613400
Address:No.198 jiangjun Road, Wuhan,China 430033
Hangzhou Gangjin Chemical Co.,Ltd.(expird)
Contact:+86-571-85109780
Address:707 Zhejiang Minhang Bldg., No.290 Zhongshan North Road, Hangzhou 310003, China
Doi:10.1021/ic50222a012
(1981)Doi:10.1155/2016/2135893
(2016)Doi:10.1039/c7ra08637g
(2017)Doi:10.1016/j.phytol.2012.12.007
(2013)Doi:10.1016/j.tet.2011.10.039
(2012)Doi:10.1002/1521-3765(20010202)7:3<671::AID-CHEM671>3.0.CO;2-M
(2001)