Journal of Organic Chemistry p. 4809 - 4812 (1993)
Update date:2022-08-04
Topics:
Takaoka, Yoshikazu
Kajimoto, Tetsuya
Wong, Chi-Huey
Two new acetamido azasugars have been synthesized and tested as inhibitors of β-N-acetylglucosaminase.Ozonolysis of enantiomerically pure N-(4-phenyl-2-azido-3-butenyl)acetamide, derived from cinnamic aldehyde, followed by lipase-catalyzed resolution of the amine intermediate 5, gave 2-azido-3-acetamidopropanal which was then condensed with dihydroxyacetone phosphate by using FDP-aldolase.The condensed product was dephospharylated and hydrogenated to afford the five-membered acetamido azasugar analogous to N-acetylglucosamine.Compounds 1 and 2 prepared in this manner were new competitive inhibitors of a β-N-acetylglucosaminidase with Ki values of 1.9 and 3.6 μM, respectively, and could be useful for the synthesis of N-acetylglucosaminyltransferase inhibitors.
View MoreShanghai Sharing technologies Co., Ltd.
Contact:86-021-66787223
Address:No11, Lane 225, Jinxiang Road,Pudong district
website:http://www.win-winchemical.com
Contact:0086-577-64498589
Address:6F, No. 396 Xingping Road, Longwan Industrial Zone, Wenzhou City, Zhejiang, 325000 P.R.China
Suzhou CarbonWell Pharma-Tech Co., Ltd
Contact:Tel: + 86 (0)512-8898-1216; + 86-18606258602
Address:2358 Changan Road, Wujiang Scientific Innovation Park, Wujiang, Jiangsu Province, P. R. China 215200
Anhui Dexinjia Biopharm Co., Ltd
Contact:+86-531-82375818
Address:9 Hexie Road, kaifaqu, Taihe
Hubei Lansun Biochemical Pharmaceutical Co., Ltd
Contact:714-6395977
Address:No. 81 Pengcheng Avenue, economic and technological development zone, Huangshi City, Hubei Province,China
Doi:10.1002/jps.2600560732
(1967)Doi:10.1021/om400945d
(2014)Doi:10.1016/S0040-4039(00)74090-1
(1993)Doi:10.1016/S0040-4020(01)81880-9
(1993)Doi:10.1021/np400668k
(2014)Doi:10.1016/j.tetlet.2013.12.081
(2014)