Journal of Organic Chemistry p. 6806 - 6812 (1995)
Update date:2022-07-29
Topics:
Brandi
Cicchi
Cordero
Frignoli
Goti
Picasso
Vogel
The structure and absolute configuration of natural lentiginosine isolated from plant sources was determined to be (1S,2S,8aS)-1,2-dihydroxyindolizidine ((+)-4) on the basis of the synthesis of both enantiomers (+)-4 and (-)-4 and their inhibition of amyloglucosidases. Alkaloid (+)-4 was derived from (L)-(+)-tartaric acid via a highly stereo- and regioselective 1,3-dipolar cycloaddition of (3S,4S)-3,4-bis[(tert-butyldiphenylsilyl)oxy]-1-pyrroline N-oxide to methylenecyclopropane, followed by thermal rearrangement of the adduct into (1S,2S,8aS)-1,2-[(tert-butyldiphenylsilyl)oxy]octahydroindolizin-7-one . The enantiomer (-)-4 was derived in the same way from (D)-(-)-tartaric acid. Both (+)-4 and (-)-4 displayed inhibition specificity for amyloglucosidases, being inactive toward 17 other glycosidases. With amyloglucosidase from Aspergillus niger, synthetic (+)-4 displayed inhibition (K(i) = 2 μM) 5 times stronger than that reported for natural lentiginosine, 35 times that measured for (-)-4, and twice that of castanospermine. Alkaloid (+)-4 is thus the most potent and specific competitive inhibitor of amyloglucosidases among azasugars and their analogues.
View MoreContact:+36(21)2523420
Address:Head office: 1102 Budapest, SZENT LASZLO TER 24/B. 1/1., HUNGARY / CHINA
Wuhan Yitongtai Science and Technology Co.,Ltd.
Contact:+86-27-88933550
Address:27th Fl. Bldg. 1, Shuian International Mansion, Heping Ave, Wuhan, Hubei, China
website:http://www.weichichem.com
Contact:+8613912949432
Address:Fine Chemical Industrial Base,Wujiang town,He County,Anhui China.
Hunan Shineway Enterprise Co., Ltd.
Contact:+86-731-86303875
Address:118, Huanghua International Airport Road, Huanghua Town, Changsha, Hunan 410137, China
CHANGZHOU HANGYU PHARMACEUTICAL TECHNOLOGY CO., LTD
website:http://www.czyys.com
Contact:0086-519-88802789
Address:No.300,Yanling Middle Road, Changzhou, Jiangsu, China
Doi:10.1021/om010524n
(2001)Doi:10.1080/00397919508011822
(1995)Doi:10.1016/S0040-4039(97)00896-4
(1997)Doi:10.1002/kin.20794
(2013)Doi:10.1016/S0040-4020(02)01180-8
(2002)Doi:10.1016/0022-1139(95)03259-G
(1995)