Lyophilization conditions for the storage of monooxygenases

Journal of Biotechnology

Volumn 203, Issue , 2015, Pages 41-44

  van Beek, Hugo L ^a   Beyer, Nina ^a   Janssen, Dick B ^a   Fraaije, Marco W ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Biocatalyst; Cryoprotection; Freeze drying; Lyophilization; Monooxygenase; Sucrose

Indexed keywords

ENZYMES; LOW TEMPERATURE DRYING; SUGAR (SUCROSE);

BAEYER-VILLIGER MONOOXYGENASES; CRYO PROTECTIONS; CYCLOHEXANONE MONOOXYGENASE; ENZYME STABILIZATION; FREEZE DRYING; LYOPHILIZATION; MONOOXYGENASES; OPTIMAL FORMULATION;

BIOCATALYSTS;

BAEYER VILLIGER MONOOXYGENASE; CYTOCHROME P450; CYTOCHROME P450 BM3; CYTOCHROME P450 MONOOXYGENASE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; BACTERIAL PROTEIN; CYCLOHEXANONE OXYGENASE; FLAVOCYTOCHROME P450 BM3 MONOXYGENASES; OXYGENASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE;

ARTICLE; CRYOPRESERVATION; ENZYME ACTIVITY; ENZYME DENATURATION; ENZYME METABOLISM; ENZYME STABILITY; ENZYME STORAGE; ENZYMOLOGY; GLASS TRANSITION TEMPERATURE; HYDROGEN BOND; LYOPHILISATE; PRIORITY JOURNAL; STORAGE TEMPERATURE; CHEMISTRY; DRUG STORAGE; FREEZE DRYING;

BACTERIAL PROTEINS; CYTOCHROME P-450 ENZYME SYSTEM; DRUG STORAGE; FREEZE DRYING; NADPH-FERRIHEMOPROTEIN REDUCTASE; OXYGENASES;

EID: 84926339478     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2015.03.010     Document Type: Article

References (34)

1. Allison S.D., Chang B., Randolph T.W., Carpenter J.F. Hydrogen bonding between sugar and protein is responsible for inhibition of dehydration-induced protein unfolding. Arch. Biochem. Biophys. 1999, 365:289-298.
2. Bauer C., Corsi C., Paolini M. Stability of microsomal monooxygenases in murine liver S9 fractions derived from phenobarbital and β-naphthoflavone induced animals under various long-term conditions of storage. Teratog. Carcinog. Mutagen. 1994, 14:13-22.
3. Beneventi E., Niero M., Motterle R., Fraaije M., Bergantino E. Discovery of Baeyer-Villiger monooxygenases from photosynthetic eukaryotes. J. Mol. Catal. B: Enzym. 2013, 98:145-154.
4. Beneventi E., Ottolina G., Carrea G., Panzeri W., Fronza G., Lau P.C.K. Enzymatic Baeyer-Villiger oxidation of steroids with cyclopentadecanone monooxygenase. J. Mol. Catal. B: Enzym. 2009, 58:164-168.
5. Blanquet S., Garrait G., Beyssac E., Perrier C., Denis S., Hébrard G., Alric M. Effects of cryoprotectants on the viability and activity of freeze dried recombinant yeasts as novel oral drug delivery systems assessed by an artificial digestive system. Eur. J. Pharm. Biopharm. 2005, 61:32-39.
6. Boddupalli S.S., Estabrook R.W., Peterson J.A. Fatty acid monooxygenation by cytochrome P-450 BM-3. J. Biol. Chem. 1990, 265:4233-4239.
7. Bong, Y.K., Clay, M.D., Collier, S.J., Mijts, B., Vogel, M., Zhang, X., Zhu, J., Nazor, J., Smith, D., & Song, S., 2013. Synthesis of prazole compounds EP2010836590.
8. Carpenter J.F., Pikal M.J., Chang B.S., Randolph T.W. Rational design of stable lyophilized protein formulations: some practical advice. Pharm. Res. 1997, 14:969-975.
9. Chefson A., Zhao J., Auclair K. Sugar-mediated lyoprotection of purified human CYP3A4 and CYP2D6. J. Biotechnol. 2007, 130:436-440.
10. Chen Y., Peoples O., Walsh C. Acinetobacter cyclohexanone monooxygenase: gene cloning and sequence determination. J. Bacteriol. 1988, 170:781-789.
11. Eastham, G.R., Johnson, D.W., Straathof, A.J.J., Fraaije, M.W., & Winter, R.T., 2013. Process for the production of methyl methacrylate WO 2013179005 A1.
12. Fink M.J., Fischer T.C., Rudroff F., Dudek H., Fraaije M.W., Mihovilovic M.D. Extensive substrate profiling of cyclopentadecanone monooxygenase as Baeyer-Villiger biocatalyst reveals novel regiodivergent oxidations. J. Mol. Catal. B: Enzym. 2011, 73:9-16.
13. Fraaije M.W., Wu J., Heuts D.P., van Hellemond E.W., Spelberg J.H., Janssen D.B. Discovery of a thermostable Baeyer-Villiger monooxygenase by genome mining. Appl. Microbiol. Biotechnol. 2005, 66:393-400.
14. Guengerich F.P. Cytochrome P450 enzymes in the generation of commercial products. Nat. Rev. Drug Discov. 2002, 1:359-366.
15. Iwaki H., Wang S., Grosse S., Bergeron H., Nagahashi A., Lertvorachon J., Yang J., Konishi Y., Hasegawa Y., Lau P.C.K. Pseudomonad cyclopentadecanone monooxygenase displaying an uncommon spectrum of Baeyer-Villiger oxidations of cyclic ketones. Appl. Environ. Microbiol. 2006, 72:2707-2720.
16. Kadow M., Loschinski K., Mallin H., Saß S., Bornscheuer U. Discovery, application and protein engineering of Baeyer-Villiger monooxygenases for organic synthesis. Org. Biomol. Chem. 2012, 10:6249-6265.
17. Leipold F., Wardenga R., Bornscheuer U.T. Cloning, expression and characterization of a eukaryotic cycloalkanone monooxygenase from Cylindrocarpon radicicola ATCC 11011. Appl. Microbiol. Biotechnol. 2012, 94:705-717.
18. Leipold F., Rudroff F., Mihovilovic M.D., Bornscheuer U.T. The steroid monooxygenase from Rhodococcus rhodochrous; a versatile biocatalyst. Tetrahedron Asymmetry 2013, 24:1620-1624.
19. Leisch H., Morley K., Lau P.C.K. Baeyer-Villiger monooxygenases: more than just green chemistry. Chem. Rev. 2011, 111:4165-4222.
20. Mansuy D. The great diversity of reactions catalyzed by cytochromes P450. Comp. Biochem. Physiol. C: Pharmacol. Toxicol. Endocrinol. 1998, 121:5-14.
21. Munro A.W., Girvan H.M., Mason A.E., Dunford A.J., McLean K.J. What makes a P450 tick?. Trends Biochem. Sci. 2013, 38:140-150.
22. Munro A.W., Leys D.G., McLean K.J., Marshall K.R., Ost T.W.B., Daff S., Miles C.S., Chapman S.K., Lysek D.A., Moser C.C., Page C.C., Dutton P.L. P450 BM3: the very model of a modern flavocytochrome. Trends Biochem. Sci. 2002, 27:250-257.
23. Opperman D.J., Reetz M.T. Towards practical Baeyer-Villiger monooxygenases: design of cyclohexanone monooxygenase mutants with enhanced oxidative stability. ChemBioChem 2010, 11:2589-2596.
24. Polizzi K.M., Bommarius A.S., Broering J.M., Chaparro-Riggers J.F. Stability of biocatalysts. Curr. Opin. Chem. Biol. 2007, 11:220-225.
25. Riva, S., Fassi, P., Allegrini, P., & Razzetti, G., 2007. A process for the preparation of (-)-modafinil EP1777295A2.
26. Ryerson C.C., Ballou D.P., Walsh C. Mechanistic studies on cyclohexanone oxygenase. Biochemistry 1982, 21:2644-2655.
27. Serdakowski A.L., Dordick J.S. Enzyme activation for organic solvents made easy. Trends Biotechnol. 2008, 26:48-54.
28. Souillac P.O., Costantino H.R., Middaugh C.R., Rytting J.H. Investigation of protein/carbohydrate interactions in the dried state. 1. Calorimetric studies. J. Pharm. Sci. 2002, 91:206-216.
29. Torres Pazmiño D.E., Riebel A., de Lange J., Rudroff F., Mihovilovic M.D., Fraaije M.W. Efficient biooxidations catalyzed by a new generation of self-sufficient Baeyer-Villiger monooxygenases. ChemBioChem 2009, 10:2595-2598.
30. Torres Pazmino D., Winkler M., Glieder A., Fraaije M. Monooxygenases as biocatalysts: classification, mechanistic aspects and biotechnological applications. J. Biotechnol. 2010, 146:9-24.
31. van Beek H.L., de Gonzalo G., Fraaije M.W. Blending Baeyer-Villiger monooxygenases: using a robust BVMO as a scaffold for creating chimeric enzymes with novel catalytic properties. Chem. Commun. 2012, 48:3288-3290.
32. van Beek H.L., Wijma H.J., Fromont L., Janssen D.B., Fraaije M.W. Stabilization of cyclohexanone monooxygenase by a computationally designed disulfide bond spanning only one residue. FEBS Open Bio 2014, 4:168-174.
33. Wang B., Tchessalov S., Warne N.W., Pikal M.J. Impact of sucrose level on storage stability of proteins in freeze-dried solids. I. Correlation of protein-sugar interaction with native structure preservation. J. Pharm. Sci. 2009, 98:3131-3144.
34. Zhao J., Auclair K. The activity of human CYP2D6 in low water organic solvents. Biotechnol. Bioeng. 2009, 102:1268-1272.