Journal of Organic Chemistry p. 2940 - 2949 (1989)
Update date:2022-08-04
Topics:
Threadgill, Michael D.
Gledhill, Adrian P.
Hydrochloride salts of S-(N-methylcarbamoyl), S-(N-ethylcarbamoyl), and S-(N,N-dimethylcarbamoyl) derivatives of cysteine, N-acetylcysteine, and cysteinylglycine have been prepared.S-(N-Methylcarbamoyl)glutathione hydrochloride has also been synthesized.Protecting groups for amino and carboxylic acid functions were selected for their ability to solubilize the peptides in dichloromethane in which solvent the thiols were treated with alkyl isocyanates and with N,N-dimethylcarbamoyl chloride.Removal of S-(amidomethyl) protecting groups using mercury(II) acetate was found to cause some loss of N-(tert-butoxycarbonyl) groups.Elimination of disulfide was evident during coupling of disulfide derivatives of cysteine using mixed anhydride methods but not with a carbodiimide coupling agent.Mixed disulfide protections were reductively cleaved by propane-1,3-dithiol.Many of the deprotected S-carbamoyl amino acids and peptides are metabolites of the corresponding N-alkylformamides in rodents and in humans.
View MoreMeryer (Shanghai) Chemical Technology Co., Ltd.
website:http://www.meryer.com/cn/index/
Contact:+86-755-86170518
Address:Minhang,Shanghai, China
Zhejiang Tianyu Pharmaceutical Co., Ltd.
Contact:+86-576-84177669, 89189665,89189688,84168770
Address:Jiangkou Development Zone, Huangyan, Taizhou City, Zhejiang
Anhui Asahikasei Chemical Co., Ltd
Contact:86-551-4259770
Address:No. 88 Linquan Road Hefei Anhui China
Nanjing lanbai chemical Co.,Ltd.
Contact:+86-25-85499326
Address:Room 908, 9F Taiyue Building,No.285 Heyan Road
KINHENG CHEMICAL(SHANGHAI)CO., LTD.
Contact:+8621-60490170
Address:Room401, No.28,Lane 189, Yangshupu Rd. Shanghai, China.
Doi:10.1016/j.dyepig.2019.107652
(2019)Doi:10.1021/jacs.5b02213
(2015)Doi:10.1016/j.bmcl.2009.10.033
(2009)Doi:10.1016/j.tetasy.2009.08.012
(2009)Doi:10.1055/s-0029-1216950
(2009)Doi:10.1016/j.bioorg.2009.09.001
(2009)