Premium
Macromolecular ionophores. 1. Chiral recognition properties of poly[(1→6)‐2,5‐anhydro‐ D ‐glucitol] toward racemic amino acid ester
Author(s) -
Kakuchi Toyoji,
Satoh Toshifumi,
Umeda Satoshi,
Mata Junji,
Yokota Kazuaki
Publication year - 1995
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530070305
Subject(s) - chemistry , macromolecule , stereochemistry , chirality (physics) , amino acid , chiral derivatizing agent , enantiomer , combinatorial chemistry , biochemistry , chiral symmetry , chiral column chromatography , physics , quantum mechanics , nambu–jona lasinio model , quark
The chiral recognition property of poly[(1→6)‐2,5‐anhydro‐3,4‐di‐ O ‐alkyl‐D‐glucitol] ( 1 ) toward racemic RCH (CO 2 CH 3 )NH 3 + · PF 6 − ( 2 · HPF 6 ) 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 = CH 2 Ph) were faster than those for aliphatic guests, 2c (R = CH(CH 3 ) 2 ) and 2d (R = CH 2 CH(CH 3 ) 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 · HPF 6 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 · HPF 6 was confirmed by 1 H and 13 C NMR spectral measurements. © 1995 Wiley‐Liss, Inc.