Optical Resolution Membranes from Polysulfones Bearing Alanine Derivatives as Chiral Selectors

✍ Scribed by Hiroaki Mizushima; Masakazu Yoshikawa; Gilles P. Robertson; Michael D. Guiver

• Book ID: 102488409
• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 370 KB
• Volume: 296
• Category: Article
• ISSN: 1438-7492
• DOI: 10.1002/mame.201000396

✦ Synopsis

Abstract

Polysulfones bearing a derivative of alanyl residue employed as chiral selectors were prepared by polymer modification. The specific rotation ([α]~D~) of the polysulfone with a derivative of D‐alanyl residue (PSf‐Ac‐D‐Ala) was determined to be 2.87 deg · cm^2^ · g^−1^ (c = 1.00 g · dL^−1^ in DMF) and that with L‐alanyl residue (PSf‐Ac‐L‐Ala) to be ‐2.36 deg · cm^2^ · g^−1^ (c = 1.00 g · dL^−1^ in DMF). The membrane from PSf‐Ac‐D‐Ala preferentially adsorbed the D‐isomer of Glu from racemic mixture of Glu and vice versa. Chiral separation ability was studied by applying a potential difference as a driving force for membrane transport. The permselectivity of PSf‐Ac‐D‐Ala toward D‐Glu (α~D/L~) was determined to be 1.40, and that of PSf‐Ac‐L‐Ala toward the L‐isomer (α~L/D~) to be 1.48 at 18.0 V, reflecting their adsorption selectivity.
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