Monoterpenes as novel substrates for oxidation and halo-hydroxylation with chloroperoxidase from Caldariomyces fumago

Applied Microbiology and Biotechnology

Volumn 73, Issue 5, 2007, Pages 1087-1096

  Kaup, Bjoern Arne ^a   Piantini, Umberto ^b   Wüst, Matthias ^b   Schrader, Jens ^a  

^a KARL WINNACKER INSTITUT   (Germany)

^b University of Applied Sciences Valais   (Switzerland)

Author keywords

Caldariomyces fumago; Chloroperoxidase; Halohydrin; Oxidation; Stereoselective; Terpenes

Indexed keywords

BIOCATALYSTS; HYDROCARBONS; HYDROGEN PEROXIDE; HYDROXYLATION; OLEFINS; OXIDATION;

CALDARIOMYCES FUMAGO; CHLOROPEROXIDASE; HALOHYDRIN; STEREOSELECTIVE; TERPENES;

ENZYME KINETICS;

3 CARENE; ALDEHYDE DERIVATIVE; BROMIDE; CHLORIDE; CHLORIDE PEROXIDASE; CITRONELLOL; GERANIOL; HALIDE; HEPTANE DERIVATIVE; HYDROCARBON; HYDROGEN PEROXIDE; IODIDE; NEROL; OXYGENASE; TERPENE;

CATALYSIS; ENZYME ACTIVITY; FUNGUS; HALIDE; HYDROGEN PEROXIDE; MONOTERPENE; ORGANOHALOGEN; OXIDANT; OXIDATION; SUBSTRATE;

ANALYSIS; ARTICLE; BIOCATALYST; CALDARIOMYCES FUMAGO; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; FUNGUS; HYDROXYLATION; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

ASCOMYCOTA; BROMIDES; CHLORIDE PEROXIDASE; CHLORIDES; CLONING, ORGANISM; ENZYME ACTIVATORS; HYDROGEN PEROXIDE; IODIDES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MONOTERPENES; OXIDANTS; OXIDATION-REDUCTION; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

LEPTOXYPHIUM FUMAGO;

EID: 33845737883     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-006-0559-3     Document Type: Article

References (49)

1. Aoun S, Babouléne M (1998) Regioselective bromohydroxylation of alkenes catalyzed by chloroperoxidase: advantages of the immobilization of enzyme on talc. J Mol Catal B Enzym 4:101-109
2. Barluenga J, Marco-Arias M, Gonzalez-Bobes F, Ballesteros A, Gonzalez JM (2004) Reaction of alkenes with hydrogen peroxide and sodium iodide: a nonenzymatic biogenic-like approach to iodohydrins. Chemistry 10(7):1677-1682
3. Bhawal BM, Joshi SN, Krishnaswamy D, Deshmukh AR (2001) (+)-3-Carene, an efficient chiral pool for the diastereoselective synthesis of β-lactams. J Indian Inst Sci 81:265-276
4. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
5. Buehler B, Schmid A (2004) Process implementation aspects for biocatalytic hydrocarbon oxyfunctionalization. J Biotechnol 113(1-3):183-210
6. Carter-Franklin JN, Butler A (2004) Vanadium bromoperoxidase-catalyzed biosynthesis of halogenated marine natural products. J Am Chem Soc 126(46):15060-15066
7. Carter-Franklin JN, Parrish JD, Tschirret-Guth RA, Little RD, Butler A (2003) Vanadium haloperoxidase-catalyzed bromination and cyclization of terpenes. J Am Chem Soc 125(13):3688-3689
8. Colonna S, Gaggero N, Casella L, Carrea G, Pasta P (1992) Chloroperoxidase and hydrogen peroxide: an efficient system for enzymatic enantioselective sulfoxidations. Tetrahedron: Asymmetry 3:95-106
9. Corey E J, Suggs W (1975) Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett 31:2647-2650
10. Dawson JH, Trudell JR, Barth G, Linder RE, Bunnenberg E, Djerassi C, Chiang R, Hager LP (1976) Letter: chloroperoxidase. Evidence for P-450 type heme environment from magnetic circular dichroism spectroscopy. J Am Chem Soc 98(12):3709-3710
11. de Carvalho CC, da Fonseca MM (2006) Biotransformation of terpenes. Biotechnol Adv 24(2):134-142
12. Demyttenaere JCR (2001) Biotransformation of terpenoids by microorganisms. In: Attar-ur-Rahman (ed) Studies in natural products chemistry, vol 25. Elsevier, Amsterdam, pp 125-178
13. Duetz WA, van Beilen JB, Witholt B (2001) Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis. Curr Opin Biotechnol 12:419-425
14. Duetz WA, Bouwmeester H, van Beilen JB, Witholt B (2003) Biotransformation of limonene by bacteria, fungi, yeast, and plants. Appl Microbiol Biotechnol 61:269-277
15. Faber K (2004) Biotransformations in organic chemistry, 5th rev and corr edn, Springer, Berlin Heidelberg New York, p 323
16. Geigert J, Dalietos DJ, Neidleman SL, Lee TD, Wadsworth J (1983a) Peroxide oxidation of primary alcohols to aldehydes by chloroperoxidase catalysis. Biochem Biophys Res Commun 114(3):1104-1108
17. Geigert J, Neidleman SL, Dalietos DJ (1983b) Novel haloperoxidase substrates. Alkynes and cyclopropanes. J Biol Chem 258(4):2273-2277
18. Hager LP, Morris DR, Brown FS, Eberwein H (1966) Chloroperoxidase. II. Utilization of halogen anions. J Biol Chem 241(8):1769-1777
19. Hager LP, Lakner FJ, Basavapathruni A (1998) Chiral synthons via chloroperoxidase catalysis. J Mol Catalysis B Enzym 5:95-101
20. Hirata T, Ikeda Y, Izumi S, Shimoda K, Hamada H, Kawamura T (1994) Introduction of oxygenated functional groups into 3-carene and 2-pinene by cultured cells. Phytochemistry 37(2):401-403
21. Hoschle B, Jendrossek D (2005) Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol. Microbiology 15:2277-2283
22. Hu S, Hager LP (1999a) Asymmetric epoxidation of functionalized cis-olefins catalyzed by chloroperoxidase. Tetrahedron Lett 40:1641-1644
23. Hu S, Hager LP (1999b) Highly enantioselective propargylic hydroxylations catalyzed by chloroperoxidase. J Am Chem Soc 121:872-873
24. Kohlmann C, Luetz S (2006) Electroenzymatic synthesis of chiral sulfoxides. Eng Life Sci 6(2):170-174
25. Lakner FJ, Hager LP (1996) Chloroperoxidase as enantioselective epoxidation catalyst: an efficient synthesis of (R)-(-)-mevalonolactone. J Org Chem 61(11):3923-3925
26. Libby RD, Thomas JA, Kaiser LW, Hager LP (1982) Chloroperoxidase halogenation reactions. Chemical versus enzymic halogenating intermediates. J Biol Chem 257(9):5030-5037
27. Lochynski S, Kowalska K, Wawrzenczyk C (2002) Synthesis and odour characteristics of new derivatives from the carane system. Flavour Fragr J 3:181-186
28. Morris DR, Hager LP (1966) Chloroperoxidase. I. Isolation and properties of the crystalline glycoprotein. J Biol Chem 241(8):1763-1768
29. Newhall WF (1958) Derivatives of (+)-Limonene. I. Esters of trans-p-menthane-1,2-diol. J Org Chem 23(9):1274-1276
30. Park JB, Clark DS (2005) New reaction system for hydrocarbon oxidation by chloroperoxidase. Biotech Bioeng 94:189-192. DOI 10.1002/bit.20769
31. Polzin JP, Rorrer GL (2003) Halogenated monoterpene production by microplantlets of the marine red alga Ochtodes secundiramea within an airlift photobioreactor under nutrient medium perfusion. Biotechnol Bioeng 82(4):415-428
32. Santhanam L, Dordick JS (2002) Chloroperoxidase-catalyzed epoxidation of styrene in aqueous and nonaqueous media. Biocatal Biotransform 20:265-274
33. Schrader J, Berger RG (2001) Biotechnological production of terpenoid flavor and fragrance compounds. In: Biotechnology, 2nd ed., Special Processes. Rehm H-J, Reed G, Pühler A, Stadler P (eds), Wiley-VCH, Weinheim, New York, 373-422
34. Seelbach K, van Deurzen MPJ, van Rantwijk F, Sheldon RA, Kragl U (1997) Improvement of the total turnover number and space-time yield for chloroperoxidase catalyzed oxidation. Biotechnol Bioeng 55:283-288
35. Sell CS (2003) A fragrant introduction to terpenoid chemistry. RSC, Cambridge
36. Sheldon RA (2000) Atom efficiency and catalysis in organic synthesis. Pure Appl Chem 72(7):1233-1246
37. Spreti N, Germani R, Incani A, Savelli G (2004) Stabilization of chloroperoxidase by polyethylene glycols in aqueous media: kinetic studies and synthetic applications. Biotechnol Prog 20(1):96-101
38. Stumpf B, Wray V, Kieslich K (1990) Oxidation of carenes to chaminic acids by Mycobacterium smegmatis DSM 43061. Appl Microbiol Biotechnol 33(3):251-254
39. Sundaramoorthy M, Terner J, Poulos TL (1998) Stereochemistry of the chloroperoxidase active site: crystallographic and molecular-modeling studies. Chem Biol 5(9):461-473
40. Urlacher V, Schmid RD (2002) Biotransformations using prokaryotic P450 monooxygenases. Curr Opin Biotechnol 13:557-564
41. Uzarewicz A, Ecianowski JO, Bakowska-Janiszewska J (2000) Synthesis and reactions of organic compounds with a nitrogen atom. Part XVI. Reactions of (-)-4-chloro-3(10)-carene and (+)-10-chloro-3-carene with phenyltelluro- and phenylselenosodium. Pol J Chem 74:1079-1083
42. van Deurzen MPJ, van Rantwijk F, Sheldon RA (1997) Selective oxidations catalyzed by peroxidases. Tetrahedron 53:13183-13220
43. van Pee KH (2001). Microbial biosynthesis of halometabolites. Arch Microbiol 175(4):250-258
44. van Pee KH, Unversucht S (2003) Biological dehalogenation and halogenation reactions. Chemosphere 52(2):299-312
45. van Rantwijk F, Sheldon RA (2000) Selective oxygen transfer catalysed by heme peroxidases: synthetic and mechanistic aspects. Curr Opin Biotechnol 11(6):554-564
46. Whitehead IM, Ohleyer EP, Dean C (1995) Bio-oxidation reactions using baker's yeast: the industrial production of short-chain acids for use in natural flavours. Bioflavour 95, Dijon (France), February 14-17, 1995. Étiévant P and Schreier P, INRA Editions Route de St. Cyr 78026 Versailles Cedex France, 245-249
47. Yamada H, Itoh N, Izumi Y (1985) Chloroperoxidase-catalyzed halogenation of trans-cinnamic acid and its derivatives. J Biol Chem 260(22):11962-11969
48. Yusubov MS, Drygunova LA, Tkachev AV, Zhdankind VV (2005) Halomethoxylation of monoterpenes using (dichloroiodo)benzene. ARKIVOC iv:179-188
49. Zaks A, Dodds DR (1995) Chloroperoxidase-catalyzed asymmetric oxidations: substrate specificity and mechanistic study. J Am Chem Soc 117:10419-10424