Combinatorial evaluation of the chiral discrimination of permethylated carbohydrates using fast-atom bombardment mass spectrometry.
The chiral discrimination abilities of several variously permethylated carbohydrates toward various amino acid 2-propyl esters were combinatorially evaluated from the relative peak intensity of the 1:1 diastereomeric complex ions with the deuterium-labeled L-amino acid 2-propyl ester protonated ion and with the unlabeled D-amino acid 2-propyl ester protonated ions in FAB mass spectrometry. The chiral discrimination abilities evaluated using FAB mass spectrometry approximately corresponded to the ratio of the association constants (K(R)/K(S)) toward each enantiomer in the solution. Therefore, this evaluation method is very useful for the screening of the chiral discrimination abilities of carbohydrates and their derivatives.
Shizuma
M
M
Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan. shizuma@omtri.city.osaka.jp
Adachi
H
H
Takai
Y
Y
Hayashi
M
M
Tanaka
J
J
Takeda
T
T
Sawada
M
M
D000596:Amino Acids / Q000737:chemistry; D002241:Carbohydrates / Q000032:analysis / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents / Q000737:chemistry; D008745:Methylation; D016339:Spectrometry, Mass, Fast Atom Bombardment / Q000379:methods*; D013237:Stereoisomerism
D000596:Amino Acids; D002241:Carbohydrates; D007202:Indicators and Reagents