Application of pH-responsive methylpropargyl leucine polymer in enantioselective crystallization

July 28, 2017

Title

Application of pH-responsive methylpropargyl leucine polymer in enantioselective crystallization

Author

Jie Zhang, Ningyu Chen, Yuheng Cui, Liqun Zhang, Dongmei Yue

Year

2016

Journal

Reactive and Functional Polymers

Abstract

In this study, novel 1-methylpropargyl alcohol derivatives containing leucine side groups on their side chains were successfully synthesized and polymerized using (nbd)Rh+[η6-C6H5B−(C6H5)3] as catalyst. Circular dichroism (CD) and ultraviolet–visible (UV–Vis) spectra revealed that the polymers took predominantly one-handed helical structures that were stable under heat. Deprotection of the t-butyloxycarboryl (Boc) groups in the homopolymers under acidic conditions produced polymers with primary amine moieties on the side chains. The polymers were soluble in aqueous medium, and turbidity test revealed that they were pH-responsive. Amino acid-based polymers were further used in the enantionselective crystallization of alanine enantiomers and l-alanine was preferably induced to crystallize with the l-leucine-based polymer.

Instrument

J-810

Keywords

Circular dichroism, Polymers, Stereochemistry