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Mechanism-inspired engineering of phenylalanine aminomutase for enhanced β-regioselective asymmetric amination of cinnamates.

Wu B, Szymański W, Wybenga GG, Heberling MM, Bartsch S, de Wildeman S, Poelarends GJ, Feringa BL, Dijkstra BW, Janssen DB
Angew Chem Int Ed Engl 51 482-6 (2012)
Cited: 13 times
EuropePMC logo PMID: 22113970

Abstract

Turn to switch: A mutant of phenylalanine aminomutase was engineered that can catalyze the regioselective amination of cinnamate derivatives (see scheme, red) to, for example, β-amino acids. This regioselectivity, along with the X-ray crystal structures, suggests two distinct carboxylate binding modes differentiated by C(β)-C(ipso) bond rotation, which determines if β- (see scheme) or α-addition takes place.

Reviews citing this publication (4)

  1. Nonproteinogenic amino acid building blocks for nonribosomal peptide and hybrid polyketide scaffolds. Walsh CT, O'Brien RV, Khosla C. Angew Chem Int Ed Engl 52 7098-7124 (2013)
  2. New generation of biocatalysts for organic synthesis. Nestl BM, Hammer SC, Nebel BA, Hauer B. Angew Chem Int Ed Engl 53 3070-3095 (2014)
  3. Enzymatic asymmetric synthesis of chiral amino acids. Xue YP, Cao CH, Zheng YG. Chem Soc Rev 47 1516-1561 (2018)
  4. Priming ammonia lyases and aminomutases for industrial and therapeutic applications. Heberling MM, Wu B, Bartsch S, Janssen DB. Curr Opin Chem Biol 17 250-260 (2013)

Articles citing this publication (9)

  1. Computational redesign of enzymes for regio- and enantioselective hydroamination. Li R, Wijma HJ, Song L, Cui Y, Otzen M, Tian Y, Du J, Li T, Niu D, Chen Y, Feng J, Han J, Chen H, Tao Y, Janssen DB, Wu B. Nat Chem Biol 14 664-670 (2018)
  2. Zymophore identification enables the discovery of novel phenylalanine ammonia lyase enzymes. Weise NJ, Ahmed ST, Parmeggiani F, Galman JL, Dunstan MS, Charnock SJ, Leys D, Turner NJ. Sci Rep 7 13691 (2017)
  3. Synthesis of d- and l-Phenylalanine Derivatives by Phenylalanine Ammonia Lyases: A Multienzymatic Cascade Process. Parmeggiani F, Lovelock SL, Weise NJ, Ahmed ST, Turner NJ. Angew Chem Weinheim Bergstr Ger 127 4691-4694 (2015)
  4. The production of L- and D-phenylalanines using engineered phenylalanine ammonia lyases from Petroselinum crispum. Tork SD, Nagy EZA, Cserepes L, Bordea DM, Nagy B, Toşa MI, Paizs C, Bencze LC. Sci Rep 9 20123 (2019)
  5. Discovery and Investigation of Mutase-like Activity in a Phenylalanine Ammonia Lyase from Anabaena variabilis. Weise NJ, Parmeggiani F, Ahmed ST, Turner NJ. Top Catal 61 288-295 (2018)
  6. Pseudomonas fluorescens Strain R124 Encodes Three Different MIO Enzymes. Csuka P, Juhász V, Kohári S, Filip A, Varga A, Sátorhelyi P, Bencze LC, Barton H, Paizs C, Poppe L. Chembiochem 19 411-418 (2018)
  7. Insight into the mechanism of aminomutase reaction: a case study of phenylalanine aminomutase by computational approach. Wang K, Hou Q, Liu Y. J Mol Graph Model 46 65-73 (2013)
  8. Fluorescent enzyme-coupled activity assay for phenylalanine ammonia-lyases. Moisă ME, Amariei DA, Nagy EZA, Szarvas N, Toșa MI, Paizs C, Bencze LC. Sci Rep 10 18418 (2020)
  9. Systematic Review Origin and Evolution of Enzymes with MIO Prosthetic Group: Microbial Coevolution After the Mass Extinction Event. Peng F, Engel U, Aliyu H, Rudat J. Front Genet 13 851738 (2022)


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