Diastereomeric recognition of chiral foldamer receptors for chiral glucoses.
[reaction: see text] Three chiral aromatic hydrazide foldamers have been designed and synthesized, in which two R- or S-proline units were incorporated at the terminals of their backbones. The 1H NMR, circular dichroism (CD), and fluorescent experiments and molecular dynamics simulations revealed that the foldamers adopted a chiral helical conformation and complexed alkylated glucoses in chloroform with a good diastereomeric selectivity.
Li
Chuang
C
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Wang
Gui-Tao
GT
Yi
Hui-Ping
HP
Jiang
Xi-Kui
XK
Li
Zhan-Ting
ZT
Wang
Ren-Xiao
RX
D002942:Circular Dichroism; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012996:Solutions; D013237:Stereoisomerism
D012996:Solutions; D005947:Glucose