Macromolecular ionophores. 1. Chiral recognition properties of poly[(1-->6)-2,5-anhydro-D-glucitol] toward racemic amino acid ester.
The chiral recognition property of poly[(1-->6)-2,5-anhydro-3,4-di-O-alkyl-D-glucitol] (1) toward racemic RCH (CO2CH3)NH3+.PF6- (2.HPF6) has been studied using a transport system involving an aqueous source and receiving phases separated by a chloroform phase containing 1. Transport rates for aromatic guests 2a (R = Ph) and 2b (R = CH2Ph) were faster than those for aliphatic guests, 2c (R = CH(CH3)2) and 2d (R = CH2CH(CH3)2), using the polymer substituted with methyl groups (1a). The enantiomeric excess (e.e.) was 10.9% for 2a as a maximum value and decreased in the order of 2a > 2c > 2b = 2d. When the transport of 2a.HPF6 was carried out using the polymers with 3,4-di-O-methyl (1a), ethyl (1b), allyl (1c), and pentyl (1d) groups, the e.e. was 22.0% for 1d as a maximum value and increased in the order of 1a < 1b < 1c < 1d. The formation of a complex between 1a and 2a.HPF6 was confirmed by 1H and 13C NMR spectral measurements.
Kakuchi
T
T
Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo, Japan.
Satoh
T
T
Umeda
S
S
Mata
J
J
Yokota
K
K
D000596:Amino Acids / Q000378:metabolism*; D001692:Biological Transport; D007476:Ionophores / Q000494:pharmacology*; D013012:Sorbitol / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000596:Amino Acids; D007476:Ionophores; D013012:Sorbitol