Counter propagation artificial neural networks modeling of an enantioselectivity of artificial metalloenzymes

Molecular Diversity

Volumn 11, Issue 3-4, 2007, Pages 141-152

  Mazurek, Sylwester ^a   Ward, Thomas R ^b   Novič, Marjana ^c  

^a UNIVERSITY OF WROC AW   (Poland)

^b UNIVERSITY OF NEUCHÂTEL   (Switzerland)

^c NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

Artificial metalloenzyme; Artificial neural networks; Enantiomeric excess; Molecular descriptors

Indexed keywords

ACETAMIDOACRYLIC ACID; ACRYLIC ACID DERIVATIVE; ENZYME; METAL; MUTANT PROTEIN; PHOSPHINE DERIVATIVE; RHODIUM COMPLEX; STREPTAVIDIN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; ARTIFICIAL NEURAL NETWORK; BIOTINYLATION; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; HYBRID; HYDROGENATION; LIGAND BINDING; MOLECULAR MODEL; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTITATIVE STRUCTURE SELECTIVITY RELATIONSHIP; SIMULATION; STATISTICAL PARAMETERS; VALIDATION PROCESS;

BIOTINYLATION; CATALYSIS; LIGANDS; METALLOPROTEINS; MODELS, MOLECULAR; MUTATION; NEURAL NETWORKS (COMPUTER); PROTEIN STRUCTURE, SECONDARY; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RHODIUM; STEREOISOMERISM; STREPTAVIDIN; SUBSTRATE SPECIFICITY;

EID: 41149149567     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-008-9068-x     Document Type: Article

References (23)

1. Ward TR (2005). Artificial metalloenzymes based on the biotin-avidin technology for the enantioselective hydrogenation of N-protected dehydroaminoacids. Chem Eur J 11: 3798-3804
2. Skander M, Kumbert N, Collot J, Gradinaru G, Klein G, Loosli A, Sauser J, Zocchi A, Gilardoni F and Ward TR (2004). Artificial metalloenzymes: (strept)avidin as host for enantioselective hydrogenation reactions using achiral biotinylated rhodium-diphosphine complexes. J Am Chem Soc 126: 14411-14418
3. Collot J, Gradinaru J, Humbert N, Skander M, Zocchi A and Ward TR (2003). Artificial metalloenzymes for enantioselective catalysis based on biotin-avidin. J Am Chem Soc 125: 9030-9031
4. Skander M, Malan C, Ivanova A and Ward TR (2005). Chemical optimization of artificial metalloenzymes based on the biotin-avidin technology: (S)-selective and solvent-tolerant hydrogenation catalysts via the introduction of chiral aminoacid spacers. Chem Commun 38: 4815-4817
5. Klein G, Humbert N, Gradinaru J, Ivanova A, Gilardoni F, Rusbandi UE and Ward TR (2005). Tailoring the active site of chemzymes using a chemogenetic optimization procedure: towards substrate-specific artificial hydrogenases based on the biotin-avidin technology. Angew Chem Int Ed 44: 7764-7767
6. Reetz MT, Peyralans JJ-P, Maichele A, Fu Y, Maywald M (2006) Direct evolution of hybrid enzymes: evolving enantioselectivity of an achiral Rh-complex anchored to a protein. Chem Commun 4318-4320
7. Kozlowski MC, Dixon SL, Panda M and Lauri G (2003). Quantum mechanical models correlating structure with selectivity: predicting the enantioselectivity of amino alcohol catalysts in aldehyde alkylation. J Am Chem Soc 125: 6614-6615
8. de Vries JG and de Vries AHM (2003). The power of high-throughput experimentation in homogeneous catalysis research for fine chemicals. Eur J Org Chem 5: 799-811
9. Aires-de-Sousa J and Gasteiger J (2005). Prediction of enantiomeric excess in a combinatorial library of catalytic enantioselective reactions. J Comb Chem 7: 298-301
10. Funar-Timofei S, Suzuki T, Paier JA, Steinreiber A, Faber K and Fabian MF (2003). Quantitative structure-activity relationships for the enantioselectivity of oxirane ring-opening catalyzed by epoxide hydrolases. J Chem Inf Comput Sci 43: 934-940
11. Melville JL, Lovelock KRJ, Wilson C, Allbutt B, Burke EK, Lygo B and Hirst JD (2005). Exploring phase-transfer catalysis with molecular dynamics and 3D/4D quantitative structure-selectivity relationships. J Chem Inf Model 45: 971-981
12. Hoogenraad M, Klaus GM, Elders N, Hooijschuur SM, McKay B, Smith AA and Damen EWP (2004). Oxazaborolidine mediated asymmetric ketone reduction: prediction of enantiomeric excess based on catalyst structure. Tetrahedron: Asymmetry 15: 519-523
13. van der Linden JB, Ras E-J, Hooijschuur SM, Klaus GM, Luchters NT, Dani P, Verspui G, Smith AA, Damen EWP, McKay B, Hoogenraad M (2005). Asymmetric catalytic ketone hydrogenation: relating substrate structure and product enantiomeric excess using QSPR. QSAR Comb Sci 24: 94-98
14. Aires-de-Sousa J, Gasteiger J, Gutman I and Vidivic D (2004). Chirality codes and molecular structure. Chem Inf Comput Sci 44: 831-836
15. Caetano S, Aires-de-Sousa J, Daszykowski M and Heyden YV (2005). Prediction of enan-tioselectivity using chirality codes and classification and regression trees. Anal Chim Acta 544: 315-326
16. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK and Olson AJ (1998). Automated docking using a lamarckian genetic algorithm and empirical binding free energy function. J Comput Chem 19: 1639-1662
17. Katritzky AR, Lobanov VS, Karelson M (1996) CODESSA reference manual, version 2.0. University of Florida
18. MATLAB®7.2.0.232 (2006) The language of technical computing. The MathWorks, Inc
19. Zupan J and Gasteiger J (1999). Neural networks in chemistry and drug design. Weinheim, VCH
20. Zupan J, Novič M and Ruisanchez I (1997). Kohonen and counterpropagation artificial neural networks in analytical chemistry. Chemom Intell Lab Syst 38: 1-23
21. Stewart JJP (1989). Optimization of parameters for semi-empirical methods I-method. J Comp Chem 10: 209-220
22. Stewart JJP (1989). Optimization of parameters for semi-empirical methods II-applications. J Comp Chem 10: 221-264
23. Novič M and Zupan J (1995). Investigation of infrared spectra-structure correlation using kohonen and counter-propagation neural network. J Chem Inf Comput Sci 35: 454-466