Enantioselective recognitions of chiral molecular tweezers containing imidazoliums for amino acids

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, respec...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2009-05, Vol.21 (5), p.539-546
Main Authors: Su, Xiaoyu, Luo, Kui, Xiang, Qingxiang, Lan, Jingbo, Xie, Rugang
Format: Article
Language:English
Subjects:
amino acid
Amylose - analogs & derivatives
Amylose - chemistry
Cellulose - chemistry
chiral recognition
Glutamic Acid - chemistry
Histidine - analogs & derivatives
Histidine - chemistry
imidazolium
Molecular Structure
molecular tweezers
Phenylalanine - chemistry
Phenylcarbamates - chemistry
Pyridines - chemistry
Stereoisomerism
UV-vis titration
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Summary: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.2PF6− showed remarkable enantioselectivity for N‐Boc protected histidine methyl ester, affording KL/KD of 5.10. Chirality, 2009. © 2008 Wiley‐Liss, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.20635