Rational design of a lipase to accommodate catalysis of Baeyer-Villiger oxidation with hydrogen peroxide

Journal of Molecular Modeling

Volumn 9, Issue 3, 2003, Pages 164-171

  Carlqvist, Peter ^a   Eklund, Robert ^a,b   Hult, Karl ^a   Brinck, Tore ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Candida antarctica Lipase B; Density functional theory; Rational design

Indexed keywords

ACETONE; ALANINE; ALKYL GROUP; CARBON; CARBONYL DERIVATIVE; HYDROGEN PEROXIDE; LIPASE B; SERINE;

AB INITIO CALCULATION; ANALYTIC METHOD; ARTICLE; ARTIFACT; AUTOMATION; BAEYER VILLIGER REACTION; BINDING AFFINITY; CALCULATION; CANDIDA ANTARCTICA; CONTROLLED STUDY; DENSITY; ENERGY; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME STRUCTURE; ENZYME SUBSTRATE COMPLEX; GENE MUTATION; MATHEMATICAL COMPUTING; MOLECULAR DYNAMICS; NONHUMAN; PRIORITY JOURNAL; QUANTUM THEORY; REACTION ANALYSIS; SIMULATION; STRUCTURE ACTIVITY RELATION; SURFACE PROPERTY;

BINDING SITES; HYDROGEN PEROXIDE; LIPASE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTATION; OXIDATION-REDUCTION; PROTEIN BINDING; QUANTUM THEORY; SUBSTRATE SPECIFICITY;

CANDIDA; CANDIDA ANTARCTICA;

EID: 0141976177     PISSN: 16102940     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00894-003-0128-y     Document Type: Article

References (35)

1. Uppenberg J, Ohrner N, Norin M, Hult K, Kleywegt GJ, Patkar S, Waagen V, Anthonsen T, Jones TA (1995) Biochemistry 34:16838-16851
2. Magnusson A, Hult K, Holmquist M (2001) J Am Chem Soc 123:4354-4355
3. Branneby C, Carlqvist P, Magnusson A, Hult K, Brinck T, Berglund P (2003) J Am Chem Soc 125:874-875
4. Plesnicar B (1983) In: Patai S (ed) The chemistry of peroxides. Wiley, Chichester, p 559 and references therein
5. Renz M, Meunier B (1999) Eur J Org Chem 4:737-750 and references therein
6. Emmons WD, Lucas GB (1955) J Am Chem Soc 77:2287-2288
7. McClure J, Williams PH (1962) J Org Chem 27:24-26
8. Walsh CT, Chen YCJ (1988) Angew Chem Int Ed Engl 27:333-343 and references therein
9. Roberts SM, Wan PWH (1998) J Mol Catal B 4:111-136 and references therein
10. Lemoult SC, Richardson PF, Roberts SM (1995) J Chem Soc Perkin Trans 1 2:89-91
11. Pchelka BK, Gelo-Pujic M, Guibé-Jampel EJ (1998) J Chem Soc Perkin Trans 1 17:2625-2627
12. Björkling F, Frykman H, Godtfredsen SE, Kirk O (1992) Tetrahedron 48:4587-4592
13. Carter P, Wells JA (1988) Nature 332:564-568
14. Stoute VA, Winnik MA, Csizmiadia IG (1974) J Am Chem Soc 96:6388-6393
15. Okuno Y (1997) Chem Eur J 3:212-218
16. Cardenas R, Cetina R, Lagunez-Otero J, Reyes L (1997) J Phys Chem A 101:192-200
17. Cardenas R, Cetina R, Lagunez-Otero J, Reyes L (2000) J Mol Struct (THEOCHEM) 497:211-225
18. Hawthorne MF, Emmons WD, McCallum KS (1958) J Am Chem Soc 80:6393-6398
19. Carlqvist P, Eklund R, Brinck T (2001) J Org Chem 66:1193-1199
20. Hu C-H, Brinck T, Hult K (1998) Int J Quantum Chem 69:89-103
21. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ (1998) J Comput Chem 19:1639-1662
22. Guex N, Peitsch MC (1997) Electrophoresis 18:2714-2723
23. Weiner SJ, Kollman PA, Case DA, Singh UC, Ghio C, Alagona G, Profeta SJ, Weiner P (1984) J Am Chem Soc 106:765-784
24. Besler BH, Merz KM, Kollman PA (1990) J Comput Chem 11:431-439
25. Åqvist J, Medina C, Samuelsson J (1994) Protein Eng 7:385-391
26. Marelius J, Hanssson T, Åqvist J (1998) Int J Quantum Chem 69:77-88
27. Kollman PA (1993) Chem Rev 93:2395-2417
28. van Gunsteren WF, Berendsen HJC (1987) Groningen molecular simulation (GROMOS) library manual. Biomos, Groningen, The Netherlands
29. Marelius J, Kolmodin K, Feierberg I, Åqvist J (1998) J Mol Graph Model 16:213-225
30. Åqvist J, van Gunsteren WF, Leijonmarck M, Tapia O (1985) J Mol Biol 183:461-477
31. Becke AD (1993) J Chem Phys 98:5648-5652
32. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785-789
33. Martin JML, EL-Yazal J, Francois J-P (1995) Mol Phys 86:1437-1450
34. Bauschlicher Jr CW, Partridge H (1995) Chem Phys Lett 240:533-540
35. Frisch MJ, Trucks GW, Schlegel HB Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann E, Burant JC, Dapprich S, Millam JM., Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98, Rev A7. Gaussian, Pittsburgh Pa.