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Enantioselective recognitions of chiral molecular tweezers containing imidazoliums for amino acids
Author(s) -
Su Xiaoyu,
Luo Kui,
Xiang Qingxiang,
Lan Jingbo,
Xie Rugang
Publication year - 2009
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.20635
Subject(s) - chemistry , enantioselective synthesis , molecular tweezers , chirality (physics) , stereochemistry , phenylalanine , titration , benzene , pyridine , histidine , amino acid , aromatic amino acids , molecule , organic chemistry , catalysis , supramolecular chemistry , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Abstract Two kinds of novel chiral molecular tweezers containing imidazoliums were synthesized from L ‐alanine, L ‐phenylalanine, and L ‐glutamic acid. They are constructed by the chiral imidazolium pincers and two different spacers which are 1,3‐bis (bromomethyl)benzene and 2,6‐bis(bromomethyl)pyridine, respectively. The enantioselective recognition of L ‐ and D ‐amino acid derivatives by these molecular tweezers was investigated by UV spectroscopic titration experiments and good enantioselectivities were obtained, which are highly sensitive to whether the spacer has the binding site and the pincers has the other aromatic rings besides imidazolium ring. The host molecular 3b.2PF 6 − showed remarkable enantioselectivity for N ‐Boc protected histidine methyl ester, affording K L / K D of 5.10. Chirality, 2009. © 2008 Wiley‐Liss, Inc.