Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides.
[structure: see text] Leaves of the edible passion fruit plant, Passiflora edulis, contain benzylic beta-D-allopyranosides 1 and 2, representatives of a rare class of natural glycosides with D-allose as the only sugar constituent. The glycoside 1 is the first known cyanogenic glycoside containing a sugar different from D-glucose attached directly to the cyanohydrin center. Asymmetric perturbation of the (1)L(b) transition of the benzene chromophore was shown to be useful for determination of absolute configuration of the cyanohydrin center of aromatic cyanogenic glycosides.
Christensen
J
J
Department of Medicinal Chemistry, Royal Danish School of Pharmacy, Universitetsparken 2, DK-2100 Copenhagen, Denmark.
Jaroszewski
J W
JW
D001547:Benzaldehydes / Q000138:chemical synthesis / Q000737:chemistry; D002942:Circular Dichroism; D005960:Glucosides; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry / Q000302:isolation & purification; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013329:Structure-Activity Relationship
D001547:Benzaldehydes; D005960:Glucosides; D006027:Glycosides; D009570:Nitriles; C432347:passiedulin; C019063:prunasin; C410942:benzyl glucopyranoside; C432348:sambunigrin