Carbohydrate Research p. 17 - 28 (1995)
Update date:2022-08-10
Topics:
Lankhorst, Peter P.
Smeets, Jan W.H.
Haasnoot, Cornelis A.G.
The two glycosides (S)-heterodendrin and (R)-epi-heterodendrin were synthesized in a novel, one-step enzymatic synthesis, and separated by means of column chromatography.The 1H NMR spectra of the two diastereoisomers differ mainly in the chemical shift of H-2' of the side chain.At first sight the 1H NMR spectra do not allow a stereospecific assignment.It was found, however, that the NOE between the anomeric proton H-1 and H-2' of the side chain is considerably larger in epi-heterodendrin than in heterodendrin, which indicates on a time-averaged basis a smallerdistance between these two protons in epi-heterodendrin.This difference in conformational behaviour is correctly reproduced by molecular mechanics calculations, thereby offering a method for the discrimination of these two glycosides.Keywords: MM2; Cyanogenic glycoside; 3D structure; Conformational analysis; Glucosidase
View MoreNanJing KaiHeng Chemical CO., LTD.
Contact:+86-25-85768391
Address:RM.1704, D, WANDA PLAZA, NO.110, MIDDLE JIANGDONG ROAD, NANJING, CHINA
Shangyu Sanhechemicals Co.,LTD.
Contact:86-0571-56696839
Address:Num.2952,Nanhuan Road,Binjiang District,Hangzhou,China
Cerametek Materials(ShenZhen)Co., Ltd.
Contact:+86-755-2324.2554
Address:A3-#9, YongChuan Street, Suite 501
Jinan Jianfeng Chemical Co., Ltd
Contact:0086-531-88110457
Address:sales01(-a-t-)pharmachemm{dot}c+o+m
lianyungang jinkang pharmaceutical technology co., ltd.
Contact:008651885445517
Address:Jinshan industrial park, Ganyu county, Lianyungang, Jiangsu Province, 222115, China
Doi:10.1016/S0040-4039(00)90884-0
(1967)Doi:10.1039/c7cc05028c
(2017)Doi:10.1002/anie.201505329
(2015)Doi:10.1063/1.1670020
(1968)Doi:10.1021/jp9532172
(1996)Doi:10.1246/cl.1977.133
(1977)