78229-03-5Relevant articles and documents
On the Analogy of Sugar Cleavages from Oligoglycosidic Natural Products by Acidic Solvolysis in Solution Chemistry and Field Desorption Mass Spectrometry
Komori, Tetsuya,Maetani, Itsuo,Okamura, Nobuyuki,Kawasaki, Toshio,Nohara, Toshihiro,Schulten, Hans-Rolf
, p. 683 - 695 (2007/10/02)
The experimental conditions for inter-laboratory reproducibility of field desorption mass spectrometry (FD-MS) for molecular weight determination and structural analysis of organic natural products were evaluated: using trillenoside B (1) as an example, the cleavages of the terminal sugar units were qualitatively and quantitatively investigated by two research groups using different instruments.The known optimal instrumental parameters then allowed parallel investigations of other oligoglycosides such as zizyphussaponin-1 (2), methyl protodioscin (3), and protodioscin(4).In accordance with the proton-induced fragmentation in FD-MS it was possible to produce by stepwise, partial acid hydrolysis three derivatives of ebelin lactone from the saponin 2.Also compound 3 treated in the same manner gave in both cases pseudodiosgenin-3,26-bis(glycoside) (5).These studies gave the first chemical evidence of the proton-induced cleavage of the glycosidic bond and the production of sequence-specific fragments in field desorption and thus confirmed its analogy.