Abstract
Polyamides with chiral environment were obtained from aromatic diamine, 1,3-phenylenediamine (1,3-PDA) or 1,4- phenylenediamine (1,4-PDA), and N-α-benzoyl-L-glutamic acid (Benzoyl-L-Glu). The optical rotation ([α]D) for 1,3- PDA-Benzoyl-L-Glu was determined to be 3.7 deg cm2 g–1, while that for 1,4-PDA-Benzoyl-L-Glu to be 9.7 deg cm2 g–1. 1,3-PDA-Benzoyl-L-Glu showed adsorption selectivity toward D-Glu and its adsorption selectivity was determined to be 1.68. Contrary to this, 1,4-PDA-Benzoyl-L-Glu showed adsorption selectivity toward L-Glu and the adsorption selectivity toward L-Glu was determined to be 1.33. From those results, those two types of chiral polyamide are expected to applicable to chiral separation or chiral recognition.
Highlights
Chirality plays an important role in biological processes [1,2]
Polyamides with chiral environment were obtained from aromatic diamine, 1,3-phenylenediamine (1,3-PDA) or 1,4phenylenediamine (1,4-PDA), and N-α-benzoyl-L-glutamic acid (Benzoyl-L-Glu)
1,4-PDA-Benzoyl-L-Glu showed adsorption selectivity toward L-Glu and the adsorption selectivity toward L-Glu was determined to be 1.33. Those two types of chiral polyamide are expected to applicable to chiral separation or chiral recognition
Summary
Chirality plays an important role in biological processes [1,2]. A given enantiomer and the corresponding antipode often exhibit different pharmacological effects. It is often observed that a drug enantiomer gives the desired effect whereas the antipode does not give the desired pharmacological effect or exhibit toxicity. The production of enantiomerically pure compounds is an important processes in various industries, involving pharmaceuticals, agrochemicals, fragrances, food additives, and so forth. Chiral separation with membranes is promising way since membrane separation can be carried out continuously under mild conditions. Membrane separation is economically and ecologically competitive to other separation methods since membrane separation, excepting pervaporation, can be operated without phase transition. Ent study, chiral polyamides were synthesized adopting N-α-benzoyl-L-glutamic acid (Benzoyl-L-Glu-OH) as a chiral building block and 1,3-phenylenediamine (1,3PDA) or 1,4-phenylenediamine (1,4-PDA) as diamine component, which is expected to give a more rigid chiral polyamide than 4,4’-diaminodiphenylmethane (DADPM) [13]
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