Polyurea With L‐Lysinyl Residues as Components: Application to Membrane Separation of Enantiomers

Abstract

Novel polyureas are synthesized from lysinyl residues. The polyurea thus prepared yields a durable self‐standing membrane that can be converted into a molecular recognition material by using Z‐D‐Glu or Z‐L‐Glu as a print molecule. The Z‐D‐Glu molecularly imprinted membrane adsorbes the D‐isomer of Glu in preference to the corresponding L‐Glu and vice versa. Even though the polyurea consists of L‐lysinyl residues, both Z‐D‐Glu and Z‐L‐Glu work as print molecules to construct molecular (chiral) recognition sites in the membrane. Those molecularly imprinted membranes show chiral separation abilities when a concentration gradient or an applied potential difference is applied as a driving force for membrane transport. magnified image

Polyurea Bearing L-Lysinyl Residue as a Chiral Building Block and Its Application to Optical Resolution

“…The introduction of long side chains would both increase the molecular weight and enhance the entanglement of polyurea chains. This would lead to the construction of durable self-standing membranes like observed in previous study (Hatanaka et al, 2011). To this end, the introduction of biuret linkage into the polyurea was attempted.…”

“…Among problems, separation of optically pure compounds is not an urgent problem to be solved but an important one to prepare for soon coming health problems. To this end, the authors' research group studied optical resolution with membranes, such as polymeric membranes with molecular recognition sites introduced by an alternative molecular imprinting (Yoshikawa & Izumi, 2003;Sueyoshi et al, 2012) and those with chiral environment or chiral selector in a main chain (Ikeuchi et al, 2009;Hatanaka et al, 2011) or in a side chain (Mizushima et al, 2011).…”

Electrospun nanofiber membranes from polysulfones with chiral selector aimed for optical resolution

“…Such transport phenomena have often been observed in chiral separation [19,22,29,30,35]. Retarded transport of enantiomer preferentially incorporated into the membrane might be due to the relatively strong interaction between the enantiomer and the membrane.…”

“…Membrane-based chiral separation has been studied in the form of liquid [12][13][14] and polymeric membranes [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] with chiral selector or chiral environment. The authors' research group studied chiral separation with molecularly imprinted membranes [17,20,22,30] and membranes [28][29][30][31] bearing amino acid residues.…”

“…The authors' research group studied chiral separation with molecularly imprinted membranes [17,20,22,30] and membranes [28][29][30][31] bearing amino acid residues.…”