ISSN:
0899-0042
Keywords:
macromolecular ionophore
;
poly[(1→6)-2,5-anhydro-3,4-di-O-alkyl-D-glucitol]
;
liquid-membrane transport
;
amino acid
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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. © 1995 Wiley-Liss, Inc.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530070305
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