A molecularly imprinted polymer-based synthetic transaminase

Journal of the American Chemical Society
Johan SvensonIan A Nicholls

Abstract

The design, synthesis, and evaluation of a molecularly imprinted polymer transaminase mimic is described. Methacrylic acid-ethylene glycol dimethacrylate copolymers were synthesized using, as a template, a transition state analogue (TSA) for the reaction of phenylpyruvic acid and pyridoxamine to yield phenylalanine and pyridoxal. Polymer suitability was established on the basis of (1)H NMR studies of template-functional monomer interactions. Polymer recognition characteristics were examined in a series of HPLC studies using the polymers as chromatographic stationary phases. Selectivity for the TSA, relative to substrates and products, was observed in both aqueous and nonpolar media. In the latter case (chloroform/AcOH, 96:4), an enantioseparation factor (alpha) of 2.1 was obtained, and frontal chromatographic studies revealed the presence of 11.9 +/- 0.2 micromol g(-1) (dry weight) of enantioselective sites. Polymers imprinted with the l-form of the oxazine-based TSA induced a 15-fold enhancement of the apparent reaction rate (app. V(max) 2.5 x 10(-7) mol s(-1); app. K(m) 8.2 x 10(-3) M) and enantioselective production of phenylalanine (32 +/- 4% ee) for reactions conducted in an aqueous buffer system. Substrate selectivity was...Continue Reading

References

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Citations

Oct 6, 2007·The Journal of Organic Chemistry·Ashootosh V AmbadeS Thayumanavan
Feb 24, 2007·Organic Letters·Subhajit BandyopadhyayRonald Breslow
Nov 15, 2008·Chemical Communications : Chem Comm·Ruizhuo OuyangHuangxian Ju
Feb 24, 2016·International Journal of Pharmaceutics·Y LongC Li
Apr 5, 2014·Journal of Molecular Recognition : JMR·Michael J WhitcombeIan A Nicholls
Jul 21, 2016·Organic Letters·Xiaoyu LanBaoguo Zhao
Mar 3, 2015·Angewandte Chemie·Yan ZhangWeiyue Lu
Jun 28, 2006·Angewandte Chemie·Maja HeitbaumIris Escher
Mar 28, 2008·Journal of Computational Chemistry·Rong-Zhen LiaoRuo-Zhuang Liu
Oct 27, 2010·Journal of Medicinal Chemistry·Björn C G KarlssonIan A Nicholls
Aug 23, 2018·The Journal of Organic Chemistry·Zi-Xuan WangAn-Xin Wu
Sep 1, 2021·Nature Communications·Weiqi CaiBaoguo Zhao
Jun 17, 2006·The Journal of Organic Chemistry·Jimmy Hedin-DahlströmIan A Nicholls
Mar 30, 2006·Journal of the American Chemical Society·Huiqi ZhangLei Ye

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