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Mirror-image packing in enantiomer discrimination molecular basis for the enantioselectivity of B.cepacia lipase toward 2-methyl-3-phenyl-1-propanol.

Mezzetti A, Schrag JD, Cheong CS, Kazlauskas RJ
Chem Biol 12 427-37 (2005)
Cited: 31 times
EuropePMC logo PMID: 15850979

Abstract

Synthetic chemists often exploit the high enantioselectivity of lipases to prepare pure enantiomers of primary alcohols, but the molecular basis for this enantioselectivity is unknown. The crystal structures of two phosphonate transition-state analogs bound to Burkholderia cepacia lipase reveal this molecular basis for a typical primary alcohol: 2-methyl-3-phenyl-1-propanol. The enantiomeric alcohol moieties adopt surprisingly similar orientations, with only subtle differences that make it difficult to predict how to alter enantioselectivity. These structures, along with a survey of previous structures of enzyme bound enantiomers, reveal that binding of enantiomers does not involve an exchange of two substituent positions as most researchers assumed. Instead, the enantiomers adopt mirror-image packing, where three of the four substituents at the stereocenter lie in similar positions. The fourth substituent, hydrogen, points in opposite directions.

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  6. Comparative Structural Analysis of Different Mycobacteriophage-Derived Mycolylarabinogalactan Esterases (Lysin B). Korany AH, Abouhmad A, Bakeer W, Essam T, Amin MA, Hatti-Kaul R, Dishisha T. Biomolecules 10 E45 (2019)
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  3. Different active-site loop orientation in serine hydrolases versus acyltransferases. Jiang Y, Morley KL, Schrag JD, Kazlauskas RJ. Chembiochem 12 768-776 (2011)
  4. Modeling of solvent-dependent conformational transitions in Burkholderia cepacia lipase. Trodler P, Schmid RD, Pleiss J. BMC Struct Biol 9 38 (2009)
  5. Enantiomeric propanolamines as selective N-methyl-D-aspartate 2B receptor antagonists. Tahirovic YA, Geballe M, Gruszecka-Kowalik E, Myers SJ, Lyuboslavsky P, Le P, French A, Irier H, Choi WB, Easterling K, Yuan H, Wilson LJ, Kotloski R, McNamara JO, Dingledine R, Liotta DC, Traynelis SF, Snyder JP. J Med Chem 51 5506-5521 (2008)
  6. A structure-controlled investigation of lipase enantioselectivity by a path-planning approach. Guieysse D, Cortés J, Puech-Guenot S, Barbe S, Lafaquière V, Monsan P, Siméon T, André I, Remaud-Siméon M. Chembiochem 9 1308-1317 (2008)
  7. The active site of an enzyme can host both enantiomers of a racemic ligand simultaneously. Mentel M, Blankenfeldt W, Breinbauer R. Angew Chem Int Ed Engl 48 9084-9087 (2009)
  8. Influence of delta-functional groups on the enantiorecognition of secondary alcohols by Candida antarctica lipase B. Nyhlén J, Martín-Matute B, Sandström AG, Bocola M, Bäckvall JE. Chembiochem 9 1968-1974 (2008)
  9. A mixed molecular modeling-robotics approach to investigate lipase large molecular motions. Barbe S, Cortés J, Siméon T, Monsan P, Remaud-Siméon M, André I. Proteins 79 2517-2529 (2011)
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  11. Molecular basis for the stereoselective ammoniolysis of N-alkyl aziridine-2-carboxylates catalyzed by Candida antarctica lipase B. Park JH, Ha HJ, Lee WK, Généreux-Vincent T, Kazlauskas RJ. Chembiochem 10 2213-2222 (2009)
  12. Kinetic modeling and docking study of immobilized lipase catalyzed synthesis of furfuryl acetate. Mathpati AC, Badgujar KC, Bhanage BM. Enzyme Microb Technol 84 1-10 (2016)
  13. A network model predicts the intensity of residue-protein thermal coupling. Censoni L, Dos Santos Muniz H, Martínez L. Bioinformatics 33 2106-2113 (2017)
  14. Mirror-Image Packing Provides a Molecular Basis for the Nanomolar Equipotency of Enantiomers of an Experimental Herbicide. Bisson C, Britton KL, Sedelnikova SE, Rodgers HF, Eadsforth TC, Viner RC, Hawkes TR, Baker PJ, Rice DW. Angew Chem Int Ed Engl 55 13485-13489 (2016)
  15. Molecular basis for competitive solvation of the Burkholderia cepacia lipase by sorbitol and urea. Oliveira IP, Martínez L. Phys Chem Chem Phys 18 21797-21808 (2016)
  16. Quantitative structure-activity relationship correlation between molecular structure and the Rayleigh enantiomeric enrichment factor. Jammer S, Rizkov D, Gelman F, Lev O. Environ Sci Process Impacts 17 1370-1376 (2015)
  17. Structural Elucidation of the Mechanism of Molecular Recognition in Chiral Crystalline Sponges. Zhang SY, Fairen-Jimenez D, Zaworotko MJ. Angew Chem Int Ed Engl 59 17600-17606 (2020)
  18. Conformational plasticity of the calcium-binding pocket in the Burkholderia glumae lipase: remodeling induced by mutation of calcium coordinating residues. Papaleo E, Invernizzi G. Biopolymers 95 117-126 (2011)
  19. Molecular mechanism of activation of Burkholderia cepacia lipase at aqueous-organic interfaces. de Oliveira IP, Jara GE, Martínez L. Phys Chem Chem Phys 19 31499-31507 (2017)
  20. Computational study of the lipase-mediated desymmetrisation of 2-substituted-propane-1,3-diamines. García-Urdiales E, Busto E, Ríos-Lombardía N, Gotor-Fernández V, Gotor V. Chembiochem 10 2875-2883 (2009)


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