A Study of the Strength of a Template Molecule-A Functional Monomer Interaction That Affects the Performance of Molecularly Imprinted Polymers and Its Application to Chiral Amplification.
A novel type of molecularly imprinted polymer (MIP), N-benzoyl-(S)-valine anilide-imprinted polymer (IP-2), was prepared using hydrogen-bonding interactions as a main force in the pre-polymerization step. The performance of the IP-2 was evaluated via batch procedure and compared with a (S)-valine anilide-imprinted polymer (IP-1) that was prepared using an ionic interaction that is stronger than hydrogen bonding. Although both polymers showed a preferential adsorbability for (S)-amino acid derivatives, different performances were observed in terms of adsorbability and enantioselectivity. In addition, the IP-2 was able to recognize the enantiomer of a valine-derived chiral catalyst. This phenomenon was applied to a chiral amplification reaction, and a highly selective asymmetric Mannich-type amination was achieved using the combination of a racemic catalyst and a MIP.
Faculty of Life Sciences, Kumamoto University.
Takuro
T
Yasuyama
Hirofumi
H
Matsunaga
Shin
S
Ando
Tadao
T
Ishizuka
D006860:Hydrogen Bonding; D054802:Molecular Imprinting; D015394:Molecular Structure; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D011108:Polymers