Novel chiral imidazole cyclophane receptors: synthesis and enantioselective recognition for amino acid derivatives.
Novel chiral imidazole cyclophane receptors were synthesized by highly selective N-alkylation of the imadazolyl 1N-position of the bridged histidine diester 2 with the dibromide in the presence of NaH; these receptors exhibit good chiral recognition toward the enantiomers of L- and D-amino acid derivatives (up to KD/KL = 3.52, delta delta G0 = -3.11 kJ mol-1) in CHCl3 at 25.0 degrees C.
You
J S
JS
Department of Chemistry,Sichuan Univeristy, Chengdu 610064, P.R. China.
Yu
X Q
XQ
Zhang
G L
GL
Xiang
Q X
QX
Lan
J B
JB
Xie
R G
RG
D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism*; D006639:Histidine / Q000737:chemistry / Q000378:metabolism; D007093:Imidazoles / Q000138:chemical synthesis* / Q000378:metabolism*; D046911:Macromolecular Substances; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D007093:Imidazoles; D046911:Macromolecular Substances; D006639:Histidine