29 Hexopyranoside p-phenybenzylエーテル誘導体のCDにおけるA値の加成性及びサポニン糖部の構造決定への応用(口頭発表の部)

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During the past few years we have been attempting to devise microanalytical techniques to determine the position of the glycoside linkages in oligosaccharides based on the exciton chirality method. In the course of these studies we have found the additivity in the amplitudes of split Cotton effects of hexopyranoside p-phenylbenzyl ethers. All 18 di-p-phenylbenzyl ethers of α-methyl glucopyranoside, mannopyranoside, and galactopyranoside were prepared to provide the standard A values of bichromophoric unit. The additivity relation was next tested by making all possible tri- and tetra-glycoside benzylates. Very good agreement was shown between A_<obs> and A_<calc> in all cases. Its application to structure determination of saponin. The Mexican plant Agave lecheguilla yields a variety of new molluscicidal saponins. One of them (AL-3) was perbenzylated with PhBnBr and NaH in DMF/THF/TMU. The analysis of the glycoside linkages was done by methanolysis of the perbenzylate in the microwave oven, subsequent HPLC of the methanolysate, and MS/UV/CD measurements of sugar benzylates. 1,4-Glycosidic linkages were identified in the glucose and galactose groups of AL-3 1.
天然有機化合物討論会の論文
1987-07-25