Production of lactones and peroxisomal beta-oxidation in yeasts

Critical Reviews in Biotechnology

Volumn 16, Issue 4, 1996, Pages 301-329

  Endrizzi, Anne ^a   Pagot, Yves ^a   Le Clainche, Annick ^b   Nicaud, Jean Marc ^b   Belin, Jean Marc ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b AGROPARISTECH   (France)

Author keywords

Beta oxidation; Biotransformation; Fatty acids; Lactones; Peroxisomes; Yeasts

Indexed keywords

LACTONE; RICINOLEIC ACID;

BIOTRANSFORMATION; CELL DIVISION; CHEMISTRY; CULTURE MEDIUM; FUNGUS; METABOLISM; MICROBODY; OXIDATION REDUCTION REACTION; PHYSIOLOGY; REVIEW; YEAST;

BIOTRANSFORMATION; CELL DIVISION; CULTURE MEDIA; FUNGI; LACTONES; MICROBODIES; OXIDATION-REDUCTION; RICINOLEIC ACIDS; YEASTS;

EID: 0030339562     PISSN: 07388551     EISSN: None     Source Type: Journal    
DOI: 10.3109/07388559609147424     Document Type: Article

References (185)

1. Abbott, B. J., Fukuda, D. S., and Archer, R. A. 1977. Microbiological transformation of cannabinoids. Experientia, 33:718-720.
2. Aitchison, J. D., Murray, W. W., and Rachubinski, R. A. 1991a. The carboxyl-terminal tripeptide Ala-Lys-Ile is essential for targeting Candida tropicalis trifunctional enzyme to yeast peroxisomes. J. Biol. Chem., 266:23197-23203.
3. Aitchison, J. D., Nuttley, W. M., Szilard, R. K., Brade, A. M., Glover, J. R., and Rachubinski, R. A. 1992. Peroxisome biogenesis in yeast. Mol. Microbiol., 6:3455-3460.
4. Aitchison, J. D., Sloots, J. A., Nuttley, W. M., and Rachubinski, R. A. 1991b. Sequence of the gene encoding Candida tropicalis peroxisomal trifunctional enzyme. Gene, 105:135-136.
5. Albrecht, W., Heidlas, J., Schwarz, M., and Tressl, R. 1992a. Biosynthesis and biotechnological production of aliphatic gamma- and delta-lactones. In: Flavors, Precursors, Thermal and Enzymatic Conversions. pp. 46-58. Teranishi, R., Takeoka, G. R., and Güntert, M., Eds., ACS Symposium Series 490, American Chemical Society, Washington, D.C.
6. Albrecht, W., Schwarz, M., Heidlas, J., and Tressl, R. 1992b. Studies on the biosynthesis of aliphatic lactones in Sporobolomyces adorus. Conversion of (S)- and (R,S)-13-hydroxy-(Z,E)-9,11 -octadecadienoic acid into optically pure (R)-delta-decalactone. J. Org. Chem., 57:1954-1956.
7. Allegrone, G., Barbeni, M., Cardillo, R., Fuganti, C., Grasselli, P., Miele, A., and Pisciotta, A. 1991. On the steric course of the microbial generation of (Z6)-gamma-dodecenolactone from (10 R,S) 10-hydroxy-octadeca-(E8,Z12)-dienoic acid. Biotechnol. Lett., 13:765-768.
8. Avers, C. J. and Federman, M. 1968. The occurrence in yeast of cytoplasmic granules which resemble microbodies. J. Cell Biol., 37:555-559.
9. Barnett, J. A., Payne, R. W., and Yarrow, D. 1983. Yeasts, Characteristics and Identification. Cambridge University Press, London.
10. Barton, P. and Page, M. I. 1993. The esterase catalysed resolution of lactones and spirodilactone. J. Chem. Soc. Perkin Trans., 2:2317-2318.
11. Belin, J. M., Bensoussan, M., and Serrano-Carreon, L. 1992. Microbial biosynthesis for the production of food flavors. Trends Food Sci. Technol., 3:11-14.
12. Berger, R. G., Neuhäuser, K., and Drawert, F. 1987. Biotechnological production of flavor compounds. III. High productivity fermentation of volatile flavors using a strain of Ischnoderma benzoinum. Biotechnol. Bioeng., 30:987-990.
13. Bonnaffé, D. and Simon, H. 1992. 5-Methoxy-pentono-1,4-lactones from (R)-2-hydroxy-5-methoxy-3-pentenoic acid obtained by bioreduction of the 2-oxo acid. Tetrahedron, 48:9695-9706.
14. Boog, A. L., Peters, A. L., and Roos, R. 1991. Process for Producing Delta-Lactones, European Patent 0.409.321.
15. Boog, A. L., van Grinsven, A. M., Peters, A. L., Roos, R., and Wieg, A. J. 1990. Process for Producing Gamma-Lactones, European Patent 0.371.568.
16. Borst, P. 1989. Peroxisome biogenesis revisited. Biochim. Biophys. Acta, 1008:1-13.
17. Bos, P. and De Bruyn, J. C. 1973. The significance of hydrocarbon assimilation in yeast identification. Antonie von Leenwenhoek, 39:99-107.
18. Brennan, P. J. and Lösel, D. M. 1978. Physiology of fungal lipids: selected topics. In: Advances in Microbial Physiology. vol. 17, pp. 47-179. Rose, A. H. and Wilkinson, J. F., Eds., Academic Press, London.
19. Buechler, K. F. and Lowenstein, J. M. 1990. The involvement of carnitine intermediates in peroxisomal fatty acid oxidation: a study with 2-bromofatty acids. Arch. Biochem. Biophys., 281:233-238.
20. Bühler, M. and Schindler, J. 1984. Aliphatic hydrocarbons. In: Biotechnology. pp. 329-385. Rehm, H. J. and Reed, G., Eds., Verlag Chemie, Weinheim.
21. 11, optically active gamma- and delta-lactones in Cladosporium suaveolens. J. Org. Chem., 54:4979-4980.
22. Cardillo, R., Fuganti, C., Barbeni, M., and Allegrone, G. 1994. Procédé pour la préparation de delta-lactones saturées par biohydrogénation des composés insaturés naturels correspondants à l'aide de microorganismes, European Patent 0.577.463.
23. Cardillo, R., Fuganti, C., Barbeni, M., Cabella, P., Guarda, P. A., and Allegrone, G. 1991. Procédé de production microbiologique des gamma- et delta-lactones, European Patent 0.412.880.
24. Cardillo, R., Fuganti, C., Sacerdote, G., Barbeni, M., Cabella, P., and Squarcia, F. 1990. Procédé de production microbiologique de décanolide gamma (R) et d'octanolide gamma (R), European Patent 0.356.291.
25. Cassio, F. and Leao, C. 1993. A comparative study on the transport of L(-)-malic acid and other short-chain carboxylic acids in the yeast Candida utilis: evidence for a general organic acid. Yeast, 9:743-752.
26. Cheetham, P. S. J. 1993. The use of biotransformations for the production of flavours and fragrances. Trends Biotechnol., 11:478-488.
27. Cheetham, P. S. J., Maume, K. A., and De Rooij, J. F. 1988. Production of Lactones, European Patent 0.258.993.
28. Collins, R. P. and Halim, A. F. 1972. Characterization of the major aroma constituent of the fungus Trichoderma viride (Pers.). J. Agric. Food Chem., 20:437-438.
29. Cooney, C. L. and Makiguchi, N. 1977. An assessment of single cell protein from methanol-grown yeasts. Biotechnol. Bioeng. Symp., 7:65-76.
30. Coudron, P. and Frerman, F. 1982. Chemical and catalytic properties of an acyl-CoA oxidase from Candida tropicalis. Ann. N. Y. Acad. Sci., 386:397-400.
31. De Andrès, C., Espuny, M. J., Robert, M., Mercades, M. E., Manresa, A., and Guinea, J. 1991. Cellular lipid accumulation by Pseudomonas aeruginosa 44T1. Appl. Microbiol. Biotechnol., 35:813-816.
32. De Duve, C. and Baudhuin, P. 1966. Peroxisomes (microbodies and related particles). Physiol. Rev., 46:323-357.
33. Dommes, P., Dommes, V., and Kunau, W. H. 1983. Beta-oxydation in Candida tropicalis. Partial purification and biological function of an inducible, 2,4-dienoyl Coenzyme-A reductase. J. Biol. Chem., 582:10846-10852.
34. Dommes, V., Baumgart, C., and Kunau, W. H. 1981. Degradation of unsaturated fatty acids in peroxisomes. Existence of a 2,4-dienoyl-CoA reductase pathway. J. Biol. Chem., 256:8259-8262.
35. Douma, A. C., Veenhuis, M., and Harder, W. 1987. A proton translocating ATPase is associated with the peroxisomal membrane of yeasts. In: Peroxisomes in Biology and Medicine. pp. 199-204. Fahimi, H. D. and Sies, H., Eds., Springer-Verlag, Berlin.
36. Drawert, F., Berger, R. G., and Neuhäuser, K. 1983. Über die biosynthese von aromastoffen durch mikroorganismen. 5: Lactone in kulturen von Polyporus durus. Chem. Mikrobiol. Technol. Lebensm., 8:91-92.
37. Dufossé, L. 1993. Production de lactones par des levures appartenant au genre Sporidiobolus. Thesis, Université de Bourgogne.
38. Dyer, J. M., McNew, J. A., and Goodman, J. M. 1996. The sorting sequence of the peroxisomal integral membrane protein PMP47 is contained within a short hydrophilic loop. J. Cell Biol., 133:269-280.
39. Einerhand, A. W. C., Kos, W., Smart, W. C., Kal, A. J., Tabak, H. F., and Cooper, T. G. 1995. The upstream region of the FOX3 gene encoding peroxisomal 3-oxoacyl-Coenzyme A thiolase in Saccharomyces cerevisiae contains ABF1- and replication Protein A-binding sites that participate in its regulation by glucose repression. Mol. Cell. Biol., 15:3405-3414.
40. Eitzen, G. A., Aitchison, J. D., Szilard, R. K., Veenhuis, M., Nuttley, W. M., and Rachubinski, R. A. 1995. The Yarrowia lipolytica gene PAY2 encodes a 42-kDa peroxisomal integral membrane protein essential for matrix protein import and peroxisome enlargement but not for peroxisome membrane proliferation. J. Biol. Chem., 270:1429-1436.
41. Elgersma, Y., van Roermund, C. W., Wanders, R. J., and Tabak, H. F. 1995. Peroxisomal and mitochondrial carnitine acetyltransferases of Saccharomyces cerevisiae are encoded by a single gene. EMBO J., 14:3472-3479.
42. Endrizzi, A. 1994. Biotransformation de ricinoléate de méthyle en gamma-décalactone par des levures. Thesis, University de Bourgogne.
43. Endrizzi, A., Awadé, A. C., and Belin, J. M. 1993. Presumptive involvement of methyl ricinoleate beta-oxidation in the production of gamma-decalactone by the yeast Pichia guilliermondii. FEMS Microbiol. Lett., 114:153-160.
44. Endrizzi, A. and Belin, J. M. 1995. Bioconversion of methyl ricinoleate to 4-hydroxy-decanoic acid and to gamma-decalactone by yeasts of the genus Candida. J. Basic Microbiol., 35:285-292.
45. Ercoli, B., Fuganti, C., Grasselli, P., Servi, S., Allegrone, G., Barbeni, M., and Pisciotta, A. 1992. Stereochemistry of the biogeneration of C-10 and C-12 gamma lactones in Yarrowia lipolytica and Pichia ohmeri. Biotechnol. Lett., 14:665-668.
46. Erdmann, R. 1994. The peroxisomal targeting signal of 3-oxoacyl-CoA thiolase from Saccharomyces cerevisiae. Yeast, 10:935-944.
47. Erdmann, R., Veenhuis, M., Mertens, D., and Kunau, W. H. 1989. Isolation of peroxisome-deficient mutants of Saccharomyces cerevisiae. Proc. Natl. Acad. Sci. U.S.A., 86:5419-5423.
48. Erdmann, R., Wiebel, F. F., Flessau, A., Rytka, J., Beyer, A., Fröhlich, K. U., and Kunau, W. H. 1991. PAS1, a yeast gene required for peroxisome biogenesis, encodes a member of a novel family of putative ATPases. Cell, 64:499-510.
49. Faber, K. N., Harder, W., Ab, G., and Veenhuis, M. 1995. Review: methylotrophic yeasts as factories for the production of foreign proteins. Yeast, 11:1331-1344.
50. Fagan, G. L., Kepner, R. E., and Webb, A. D. 1981. Biosynthesis of certain gamma-substituted-gamma-butyrolactones present in film sherries. Am. J. Enol. Vitic., 32:163-167.
51. Farbood, M. I., McLean, L. B., Morris, J. A., and Bondarovich, H. A. 1992. Octalactone-Containing Composition, Fermentation Process for Producing Same and Organoleptic Uses Thereof, U.S. Patent 5.112.803.
52. Farbood, M. I., Morris, J. A., and McLean, L. B. 1994. Fermentation Process for Preparing 10-Hydroxy-C18-Carboxylic Acid and Gamma-Dodecalactone Derivatives, European Patent 0.578.388.
53. Farbood, M. I., Morris, J. A., Sprecker, M. A., Bienkowski, L. J., Miller, K. P., Vock, M. H., and Hagedorn, M. L. 1990. Process for Preparing Compositions Containing Unsaturated Lactones, Products Produced Thereby and Organoleptic Uses of Said Products, European Patent 0.354.000.
54. Farbood, M. I. and Willis, B. J. 1983. Production of Gamma-Decalactone, International Patent PCT WO 83/01072.
55. Fuganti, C., Grasselli, P., and Barbeni, M. 1991. Biogeneration of aromas: gamma and delta lactones from C6 to C12. NATO ASI Ser., Ser. A, 207:1-17.
56. Fuganti, C., Servi, S., Barbeni, M., and Cabella, P. 1993. New avenues in natural products: strategies in the biogeneration of flavors. In: Studies in Natural Products Chemistry. vol. 13, pp. 295-345. Atta-ur-Rahman, Ed., Eisevier Science Publishers, B.V.
57. Fukui, S., Kawamoto, S., Yasuhara, S., Tanaka, A., Osumi, M., and Imaizumi, F. 1975a. Microbodies of methanol-grown yeasts: localization of catalase and flavin-dependent alcohol oxidase in the isolated microbody. Eur. J. Blochem., 59:561-566.
58. Fukui, S., Tanaka, A., Kawamoto, S., Yasuhara, S., Teranishi, Y., and Osumi, M. 1975b. Ultrastructure of methanol-utilizing yeast cells: appearance of microbodies in relation to high catalase activity. J. Bacteriol., 123:317-328.
59. Gatfield, I. L. 1986. Generation of flavor and aroma components by microbial fermentation and enzyme engineering technology. In: Biogeneration of Aromas. pp. 310-322. Parliment, T. and Croteau, R., Eds., ACS Symposium Series 317, American Chemical Society, Washington, D.C.
60. Gatfield, I. L., Güntert, M., Sommer, H., and Werkhoff, P. 1993. Some aspects of the microbiological production of flavor-active lactones with particular reference to gamma-decalactone. Chem. Mikrobiol. Technol. Lebensm., 15:165-170.
61. Ghisalberti, E. I., Narbey, M. J., Dewan, M. M., and Sivasithamparam, K. 1990. Variability among strains of Trichoderma harzianum in their ability to reduce take-all and to produce pyrones. Plant Soil, 121:287-291.
62. Gill, C. O., Hall, M. G., and Ratledge, C. 1977. Lipid accumulation in an oleaginous yeast (Candida 107) growing in glucose in single state continuous culture. Appl. Environ. Microbiol., 33:231-239.
63. Glover, J. R., Andrews, D. W., Subramani, S., and Rachubinski, R. A. 1994. Mutagenesis of the amino targeting signal of Saccharomyces cerevisiae 3-keto-acyl-CoA thiolase reveals conserved amino acids required for import into peroxisomes in vivo. J. Biol. Chem., 269:7558-7563.
64. Goodman, J. M., Trapp, S. B., Hwang, H., and Veenhuis, M. 1990. Peroxisomes induced in Candida boidinii by methanol, oleic acid and D-alanine vary in metabolic function but share common integral membrane proteins. J. Cell Sci., 97:193-204.
65. Gould, S. J., Keller, G. A., and Subramani, S. 1987. Identification of a peroxisomal targeting signal at the carboxy terminus of firefly luciferase. J. Cell Biol., 105:2923-2931.
66. Gould, S. J., Keller, G. A., and Subramani, S. 1988. Identification of peroxisomal targeting signals located at the carboxy terminus of four peroxisomal proteins. J. Cell Biol., 107:897-905.
67. Gould, S. J., Keller, G. A., Hosken, N., Wilkinson, J., and Subramani, S. 1989. A conserved tripeptide sorts proteins to peroxisomes. J. Cell Biol., 108:1657-1664.
68. Gould, S. J., Keller, G. A., Schneider, M., Howell, S. H., Garrard, L. J., Goodman, J. M., Distel, B., Tabak, H., and Subramani, S. 1990. Peroxisomal protein import is conserved between yeast, plants, insects and mammals. EMBO J., 9:85-90.
69. Haffner, T. and Tressl, R. 1996. Biosynthesis of (R)-γ-decanolactone in the yeast Sporobolomyces odorus. J. Agric. Food Chem., 44:1218-1223.
70. Hasegawa, Y., Tsujimoto, H., Obata, H., and Tokuyama, T. 1992. The metabolism of cyclohexanol by Exophiala jeanselmei, Biosci. Biotech. Biochem., 56:1319-1320.
71. Hashimoto, T. 1982. Individual peroxisomal beta-oxidation enzymes. Ann. N. Y. Acad. Sci., 386:5-12.
72. Hiltunen, J. K., Wenzel, B., Beyer, A., Erdmann, R., Fossa, A., and Kunau, W. H. 1992. Peroxisomal multifunctional beta-oxidation protein of Saccharomyces cerevisiae. Molecular analysis of the FOX2 gene and gene product. J. Biol. Chem., 267:6646-6653.
73. Höhfeld, J., Veenhuis, M., and Kunau, W. H. 1991. PAS3, a Saccharomyces cerevisiae gene encoding a peroxisomal integral membrane protein essential for peroxisome biogenesis. J. Cell Biol., 114:1167-1178.
74. Igual, J. C., Gonzales-Bosch, C., Franco, L., and Perez-Ortin, J. 1992. The POT1 gene for yeast peroxisomal thiolase is subject to three different mechanisms of regulation. Mol. Microbiol., 6:1867-1875.
75. Iida, M., Wakuri, S., Mineki, S., Nishitani, K., and Yamakawa, K. 1993. Microbial hydroxylation of 11,13-dehydrosantonin by Aspergillus niger. J. Ferm. Bioeng., 76:296-299.
76. Inestrosa, N. C., Bronfman, M., and Leighton, F. 1979. Detection of peroxisomal fatty acyl-Coenzyme A oxidase activity. Biochem. J., 182:779-788.
77. Issemann, I., Prince, R., Tugwood, J., and Green, S. 1992. A role for fatty acids and liver fatty acid binding protein in peroxisome proliferation. Biochem. Soc. Trans., 20:824-827.
78. Ito, S. and Inoue, S. 1982. Sophorolipids from Torulopsis bombicola: Possible relation to alkane uptake. Appl. Environ. Microbiol., 43:1278-1283.
79. Janssens, J. H., Burris, N., Woodward, A., and Bailey, R. B. 1983. Lipid-enhanced ethanol production by Kluyveromyces fragilis. Appl. Environ. Microbiol., 45:598-602.
80. Kalish, J. E., Chen, C. I., Gould, S. J., and Watkins, P. A. 1995a. Peroxisomal activation of long- and very long-chain fatty acids in the yeast Pichia pastoris. Biochem. Biophys. Res. Commun., 206:335-340.
81. Kalish, J. E., Theda, C., Morrell, J. C., Berg, J. M., and Gould, S. J. 1995b. Formation of the peroxisome lumen is abolished by loss of Pichia pastoris Pas7p, a zinc-binding integral membrane protein of the peroxisome. Mol. Cell. Biol., 15:6406-6419.
82. Katayama-Hirayama, K., Tobita, S., and Hirayama, K. 1991. Degradation of phenol by yeast Rhodotorula. J. Gen. Appl. Microbiol., 37:147-156.
83. Kawamoto, S., Nozaki, C., Tanaka, A., and Fukui, S. 1978. Fatty acid beta-oxidation system in microbodies of n-alkane-grown Candida tropicalis. Eur. J. Biochem., 83:609-613.
84. Kersten, P. J., Dagley, S., Whittaker, J. W., Arciero, D. M., and Lipscomb, J. D. 1982. 2-Pyrone-4,6-dicarboxylic acid, a catabolite of gallic acids in Pseudomonas species. J. Bacteriol., 152:1154-1162.
85. Kim, C. H., Endo, T., and Yonehara, H. 1988. Studies on mikamycin B lactonase. V. Metabolic control in mikamycin B fermentation. J. Antibiot. (Tokyo), 41:73-80.
86. Kleber, H. P., Asperger, O., Stüwer, O., Stüwer, B., and Hommel, R. 1989. Occurrence and regulation of cytochrome P450 in Torulopsis apicola. In: Cytochrome P450: Biochemistry and Biophysics. Proc. 6th Int. Conf. Biochemistry and Biophysics of Cytochrome P450. pp. 169-172. Schuster, I., Ed., Taylor & Francis Press, London.
87. Klug, M. J. and Markovets, A. J. 1967. Degradation of hydrocarbons by members of the genus Candida. I. Hydrocarbon assimilation. Appl. Microbiol., 15:690-693.
88. Klug, M. J. and Markovets, A. J. 1971. Utilization of aliphatic hydrocarbons by microorganisms. In: Advances in Microbial Physiology. vol. 5, pp. 1-43. Rose, A. H. and Wilkinson, J. F., Eds., Academic Press, London.
89. Kohlwein, S. D. and Paltauf, F. 1983. Uptake of fatty acids by the yeasts Saccharomyces uvarum and Saccharomyces lipolytica. Biochim. Biophys. Acta, 792:310-317.
90. Kunau, W. H., Kionka, C., Ledebur, A., Mateblowski, M., Moreno de la Garza, M., Schultz-Borchard, U., Thieringer, R., and Veenhuis, M. 1987. Beta-oxidation systems in eukaryotic microorganisms. In: Peroxisomes in Biology and Medicine. pp. 128-140. Fahimi, H. D. and Sies, H., Eds., Springer-Verlag, Berlin.
91. Labows, J. N., Horsham, J., Webster, G., Hill, L., and Mac Ginley, K. 1983. Production of Gamma-Lactone Rich Flavor Additives by Pityrosporum Species Cultured on Lipid Rich Substrates, U.S. Patent 4.396.715.
92. Lanza, E., Ko, K. H., and Palmer, J. K. 1976. Aroma production by cultures of Ceratocystis moniliformis. J. Agric. Food Chem., 24:1247-1250.
93. Latrasse, A., Guichard, E., Piffaut, C., Fournier, N., and Dufossé, L. 1993. Chirality of the gamma-lactones formed by Fusarium poae INRA 45. Chirality, 5:379-384.
94. Lazarow, P. B. 1995. Peroxisome structure, function, and biogenesis-human patients and yeast mutants show strikingly similar defects in peroxisome biogenesis. J. Neuropathol. Exp. Neurol., 54:720-725.
95. Lazarow, P. B., Small, G. M., Imanaka, T., Shio, H., Alexson, S., Mortensen, R. M., Rachubinski, R. A., and Fujiki, Y. 1987. Biogenesis of peroxisomes in rat liver and Candida Tropicalis. In: Peroxisomes in Biology and Medicine. pp. 394-401. Fahimi, H. D. and Sies, H., Eds., Springer-Verlag, Berlin.
96. Levi, J. D., Shennan, J. L., and Ebbon, G. P. 1979. Biomass from liquid n-alkanes. In: Economic Microbiology. pp. 361-419. Rose, A. H., Ed., Academic Press, London.
97. Liu, H., Tan, X., Russell, K. A., Veenhuis, M., and Cregg, J. M. 1995. PER3, a gene required for peroxisome biogenesis in Pichia pastoris, encodes a peroxisomal membrane protein involved in protein import. J. Biol. Chem., 270:10940-10951.
98. Maga, J. A. 1976. Lactones in foods. CRC Crit. Rev. Food Sci. Nutr., 8:1-56.
99. Mannaerts, G. P., Debeer, L. J., Thomas, J., and De Schepper, P. J. 1979. Mitochondrial and peroxisomal fatty acid oxidation in liver homogenates and isolated hepatocytes from control and clofibrate-treated rats. J. Biol. Chem., 254:4585-4595.
100. Marchal, R., Metche, M., and Vandecasteele, J. P. 1982. Hydroxylation of alkanes and fatty acids in Saccharomycopsis lipolytica. Evidence for the involvement of cytochrome P450. J. Gen. Microbiol., 128:1125-1134.
101. Maruyama, K. 1983. Purification and properties of 2-pyrone-4,6-dicarboxylate hydrolase. J. Biochem., 93:557-565.
102. Marzioch, M., Erdmann, R., Veenhuis, M., and Kunau, W. H. 1994. PAS7 encodes a novel yeast member of the WD-40 protein family essential for import of 3-oxoacyl-CoA thiolase, a PTS2-containing protein, into peroxisomes. EMBO J., 13:4908-4918.
103. McNew, J. A. and Goodman, J. M. 1996. The targeting and assembly of peroxisomal proteins: some old rules do not apply. Trends Biochem. Sci., 21:54-58.
104. Meisel, M. N., Kozlova, T. M., Medvedeva, G. A., Novichkova, A. T., Pomoshchnikova, N. A., and Seliverstova, L. A. 1977. Yeast peroxisomes, their development and functioning. Mikrobiologiya, 46:835-845.
105. Meisel, M. N., Medvedeva, G. A., and Kozlova, T. M. 1976. Cytological mechanisms of the assimilation of n-alkanes by yeast. Mikrobiologiya, 45:844-851.
106. Meyer, J. 1993. Verbessertes Verfahren zur fermentativen Herstellung von gamma-Lactonen, German Patent 4.126.997.
107. Mishina, M., Kamiryo, T., Tashiro, S., Hagihara, T., Tanaka, A., Fukui, S., Osumi, M., and Numa, S. 1978. Subcellular localization of two long-chain acyl-Coenzyme A synthetases in Candida lipolytica. Eur. J. Biochem., 89:321-328.
108. Mishina, M., Yanagawa, S., Tanaka, A., and Fukui, S. 1973. Physiology and metabolism of hydrocarbon-utilizing microorganisms. V. Effects of chain length of alkane substrate on fatty acid composition and biosynthesis pathway in some Candida yeast. Agric. Biol. Chem., 37:863-870.
109. Mizugaki, M., Uchiyama, M., and Okui, S. 1965. Metabolism of hydroxy fatty acids. V: Metabolic conversion of homoricinoleic and homoricinelaidic acids by Escherichia coli K12. J. Biochem. (Tokyo), 58:273-278.
110. Moreno de la Garza, M., Schultz-Borchard, U., Crabb, J. W., and Kunau, W. H. 1985. Peroxisomal beta-oxidation system of Candida tropicalis. Eur. J. Biochem., 148:285-291.
111. Mosandl, A. and Günther, C. 1989. Stereoisomeric flavor compounds. 20. Structure and properties of gamma-lactone enantiomers. J. Agric. Food Chem., 37:413-418.
112. Murray, W. W. and Rachubinski, R. A. 1987. The primary structure of a peroxisomal fatty acyl-CoA oxidase from the yeast Candida tropicalis pK233. Gene, 51:119-128.
113. Muys, G. T., Van der Ven, B., and De Jonge, A. P. 1962. Synthesis of optically active gamma- and delta-lactones by microbial reduction. Nature, 194:995-996.
114. Nago, H., Matsumoto, M., and Nakai, S. 1993a. 2-Deceno-delta-lactone-producing fungi, strains of Fusarium solani, isolated by using a medium containing decano-delta-lactone as the sole carbon source. Biosci. Biotech. Biochem., 57:2107-2110.
115. Nago, H., Matsumoto, M., and Nakai, S. 1993b. Degradative pathway of 2-Deceno-delta-lactone by the lactone-producing fungus, Fusarium solani. Biosci. Biotech. Biochem., 57:2111-2115.
116. Ngai, K. L., Schlömann, M., Knackmuss, H. J., and Ornston, L. N. 1987. Dienelactone hydrolase from Pseudomonas sp. strain B13. J. Bacteriol., 169:699-703.
117. 31P NMR study of the internal pH of yeast peroxisomes. Arch. Microbiol., 147:37-41.
118. Nuttley, W. M., Aitchison, J. D., and Rachubinski, R. A. 1988. cDNA cloning and primary structure determination of the peroxisomal trifunctional enzyme hydratase-dehydrogenase-epimerase from the yeast Candida tropicalis pK233. Gene, 69:171-180.
119. Okada, H., Ueda, M., Sugaya, T., Atomi, H., Mozzafar, S., Hishida, T., Teranishi, Y., Okazaki, K., Takechi, T., Kamiryo, T., and Tanaka, A. 1987. Catalase gene of the yeast Candida tropicalis. Sequence analysis and comparison with peroxisomal and cytosolic catalases from other sources. Eur. J. Biochem., 170:105-110.
120. Okazaki, K., Tan, H., Fukui, S., Kubota, I., and Kamiryo, T. 1987. Peroxisomal acyl-coenzyme A oxidase multigene family of the yeast Candida tropicalis; nucleotide sequence of a third gene and its protein product. Gene, 58:37-44.
121. Okui, S., Uchiyama, M., and Mizugaki, M. 1963a. Metabolism of hydroxy fatty acids. I: Metabolic conversion of ricinoleic acid by a certain microorganism to 8-D-(+)-hydroxy-tetradec-cis-5-enoic acid. J. Biol. Chem., 53:265-270.
122. Okui, S., Uchiyama, M., and Mizugaki, M. 1963b. Metabolism of hydroxy fatty acids. II: Intermediates of the oxidative breakdown of ricinoleic acid by genus Candida. J. Biochem. (Tokyo), 54:536-540.
123. Osmundsen, H., Bremer, J., and Pedersen, J. I. 1991. Metabolic aspects of peroxisomal beta-oxidation. Biochim. Biophys. Acta, 1085:141-158.
124. Osumi, T., Tsukamoto, T., Hata, S., Yokota, S., Miura, S., Fujiki, Y., Hijikata, M., Miyazawa, S., and Hashimoto, T. 1991. Amino-terminal presequence of the precursor of peroxisomal 3-ketoacyl-CoA thiolase is a cleavable signal peptide for peroxisomal targeting. Biochem. Biophys. Res. Commun., 181:947-954.
125. Page, G. V. and Eilerman, R. G. 1989. Process for the Preparation of Gamma and Delta Lactones, International Patent PCT WO 89/12104.
126. Pagot, Y. and Belin, J. M. 1996. Fatty acid cellular metabolism and lactone production by the yeast Pichia guilliermondii. Appl. Microbiol. Biotechnol. 45: 349-354.
127. Parish, R. W. 1975. The isolation and characterization of peroxisomes (microbodies) from baker's yeast, Saccharomyces cerevisiae. Arch. Microbiol., 105:187-192.
128. Pickenhagen, W. 1989. Enantioselectivity in odor perception. In: Flavor Chemistry, Trends and Developments. pp. 151-157. Teranishi, R., Buttery, R. G., and Shahidi, F., Eds., ACS Symposium Series 388, American Chemical Society, Washington, D.C.
129. Pittet, A. O. and Klaiber, E. M. 1975. Synthesis and flavor properties of some alkyl-substituted alpha-pyrone derivatives. J. Agric. Food Chem., 23:1189-1195.
130. Prasad, R. and Rose, A. H. 1986. Involvement of lipids in solute transport in yeasts. Yeast, 2:205-220.
131. Purdue, P. E. and Lazarow, P. B. 1994. Peroxisomal biogenesis: multiple pathways of protein import. J. Biol. Chem., 269:30065-30068.
132. Purdue, P. E. and Lazarow, P. B. 1995. Identification of peroxisomal membrane ghosts with an epitope-tagged integral membrane protein in yeast mutants lacking peroxisomes. Yeast, 11:1045-1060.
133. Rachubinski, R. A., Fujiki, Y., and Lazarow, P. B. 1985. Cloning of cDNA coding for peroxisomal acyl-CoA oxidase from the yeast Candida tropicalis pK233. Proc. Natl. Acad. Sci. U.S.A., 82:3973-3977.
134. Rachubinski, R. A., Fujiki, Y., and Lazarow, P. B. 1987. Isolation of cDNA clones coding for peroxisomal proteins of Candida tropicalis: identification and sequence of a clone for catalase. Biochim. Biophys. Acta, 909:35-43.
135. Radwansky, A. and Lehman, J. 1993. Lactones XXVII: lactonized pimocide-stability and dopamine receptor affinity of its enantiomers and ring open derivatives. Arch. Pharm. (Weinheim), 326:911-912.
136. Ratledge, C. 1984. Microbial conversions of alkanes and fatty acids. JAOCS, 61:447-453.
137. Ratledge, C. and Evans, C. T. 1989. Lipids and their metabolism. In: The Yeasts. vol. 3, pp. 367-455. Rose, A. H. and Harrison, J. S., Eds., Academic Press, London.
138. Sarris, J. and Latrasse, A. 1985. Production of odoriferous gamma-lactones by Fusarium poae. Agric. Biol. Chem., 49:3227-3230.
139. Schepers, L., Van Veldhoven, P. P., Casteels, M., Eyssen, H. J., and Mannaerts, G. P. 1990. Presence of three acyl-CoA oxidases in rat liver peroxisomes. J. Biol. Chem., 265:5242-5246.
140. Serrano-Carreon, L., Hathout, Y., Bensoussan, M., and Belin, J. M., 1992. Production of 6-pentyl-alpha-pyrone by Trichoderma harzianum from 18 : n fatty acid methyl esters. Biotechnol. Lett., 14:1019-1024.
141. Serrano-Carreon, L., Hathout, Y., Bensoussan, M., and Belin, J. M. 1993. Metabolism of linoleic acid or mevalonate and 6-pentyl-alpha-pyrone biosynthesis by Trichoderma species. Appl. Environ. Microbiol., 59:2945-2950.
142. Shimizu, S., Kataoka, M., Shimizu, K., Hirakata, M., Sakamoto, M., and Yamada, H. 1992. Purification and characterization of a novel lactonohydrolase, catalysing the hydrolysis of aldonate lactones and aromatic lactones, from Fusarium oxysporum. Eur. J. Biochem., 209:383-390.
143. Shimizu, S., Yasui, K., Tani, Y., and Yamada, H. 1979. Acyl-CoA oxidase from Candida tropicalis. Biochem. Biophys. Res. Commun., 91:108-113.
144. Skoneczny, M., Cheltowska, A., and Rytka, J. 1988. Study of the coinduction by fatty acids of catalase A and acyl-CoA oxidase in standard and mutant Saccharomyces cerevisiae strains. Eur. J. Biochem., 174:297-302.
145. Small, G. M., Szabo, L. J., and Lazarow, P. B. 1988. Acyl-CoA oxidase contains two targeting sequences each of which can mediate protein import into peroxisomes. EMBO J., 7: 1167-1173.
146. Spinnler, H. E., Dufossé, L., Souchon, I., Latrasse, A., Piffaut-Juffard, C., Voilley, A., and Delest, P. 1994. Production de gamma-décalactone par bioconversion, French Patent 2.705.971.
147. Subramani, S. 1993. Protein import into peroxisomes and biogenesis of the organelle. Annu. Rev. Cell Biol., 9:445-478.
148. Sutler, G. J., Verheyden, K., Mannaerts, G., Harder, W., and Veenhuis, M. 1993. The in vitro permeability of yeast peroxisomal membranes is caused by a 31 kDa integral membrane protein. Yeast, 9:733-742.
149. Swinkels, B. W., Gould, S. J., Bodnar, A. G., Rachubinski, R. A., and Subramani, S. 1991. A novel, cleavable peroxisomal targeting signal at the amino-terminus of the rat 3-ketoacyl-CoA thiolase. EMBO J., 10:3255-3262.
150. Tahara, S., Fujiwara, K., Ishizaka, H., Mizutani, J., and Obata, Y. 1972. Gamma-decalactone, one of constituents of volatiles in cultured broth of Sporobolomyces odorus. Agric. Biol. Chem., 36:2585-2587.
151. Tan, X., Waterham, H. R., Veenhuis, M., and Cregg, J. M. 1995. The Hansenula polymorpha PER8 gene encodes a novel peroxisomal integral membrane protein involved in proliferation. J. Cell Biol., 128:307-319.
152. Tanaka, A. and Fukui, S. 1981. The roles of yeast peroxisomes in alkane metabolism. In: Current Developments in Yeast Research. Advances in Biotechnology. pp. 423-428. Stewart, G. G. and Russel, I., Eds., Pergamon Press, Toronto.
153. Tanaka, A. and Fukui, S. 1989. Metabolism of n-alkanes. In: The Yeasts. vol. 3, pp. 261-287. Rose, A. H. and Harrison, J. S., Eds., Academic Press, London.
154. Tanaka, A., Osumi, M., and Fukui, S. 1982. Peroxisomes of alkane-grown yeast: fundamental and practical aspects. Ann. N. Y. Acad. Sci., 386: 183-199.
155. Tanaka, A., Sonomoto, K., and Ueda, M. 1988. Functions, biogenesis and immobilization of yeast peroxisomes. In: Proc. 8th Int. Biotechnology Symp. vol. 1, pp. 350-360. Durand, G., Bobichon, L., and Florent, J., Eds., Société Française de Microbiologie, Paris.
156. Teranishi, Y., Kawamoto, S., Tanaka, A., and Fukui, S. 1974b. Physiology and metabolism of hydrocarbon-utilizing microorganisms. VII. Induction of catalase activity by hydrocarbon in Candida tropicalis. Agric. Biol. Chem., 38:1221-1225.
157. Teranishi, Y., Tanaka, A., Osumi, M., and Fukui, S. 1974a. Physiology and metabolism of hydrocarbon-utilizing microorganisms. VI. Catalase activities of hydrocarbon-utilizing Candida yeasts. Agric. Biol. Chem., 38:1213-1220.
158. Thomas, J., Debeer, L. J., De Schepper, P. J., and Mannaerts, G. P. 1980. Factors influencing palmitoyl-CoA oxidation by rat liver peroxisomal fractions. Biochem. J., 190:485-494.
159. Titorenko, V. I., Keizer, I., Harder, W., and Veenhuis, M. 1995. Isolation and characterization of mutant impaired in the selective degradation of peroxisomes in the yeast Hansenula polymorpha. J. Bacteriol., 177:357-363.
160. Tressl, R., Apetz, M., Arrieta, R., and Grünewald, K. G. 1978. Formation of lactones and terpenoids by microorganisms. In: Flavor of Foods and Beverages: Chemistry and Technology. pp. 145-168. Charalambous, G. and Inglett, G. E., Eds., Academic Press, New York.
161. Tressl, R., Heidias, J., Albrecht, W., and Engel, K. H. 1988. Biogenesis of chiral hydroxyacid esters. In: Bioflavour' 87, Proc. Int. Conf. 1987. pp. 221-236. Schreier, P., Ed., Walter de Gruyter, Berlin.
162. Tulloch, A. P., Hill, A., and Spencer, J. F. T. 1968. Structure and reactions of lactonic and acidic sophorosides of 17-hydroxyoctadecanoic acid. Can. J. Biochem., 46:3337-3351.
163. Tuttle, D. L. and Dunn, W. A. 1995. Divergent modes of autophagy in the methylotrophic yeast Pichia pastoris. J. Cell Sci., 108:25-35.
164. Ueda, M., Mozaffar, S., Atomi, H., Osumi, M., and Tanaka, A. 1989. Characterization of peroxisomes in an n-alkane-utilizable yeast, Candida tropicalis, grown on glucose and propionate. J. Ferm. Bioeng., 68:411-416.
165. Ueda, M., Mozzafar, S., and Tanaka, A. 1990. Catalase from Candida boidinii 2201. Methods Enzymol., 188:463-467.
166. Ueda, M., Yamanoi, K., Morikawa, T., Okada, H., and Tanaka, A. 1985. Peroxisomal localization of enzymes related to fatty acid beta-oxidation in an n-alkane-grown yeast, Candida tropicalis. Agric. Biol. Chem., 49:1821-1828.
167. Urbach, G. 1982. The effect of different feeds on the lactone and methyl ketone precursors of milk fat. Lebensm.-Wiss. U.-Technol., 15:62-67.
168. Vamecq, J. 1987. Chlorpromazine and carnitine-dependency of rat liver peroxisomal beta-oxidation of long chain fatty acids. Biochem. J., 241:783-791.
169. Van der Schaft, P. H. and de Laat, W. T. 1991. Natural Delta-Lactones and Process of the Production Thereof, European Patent 0.425.001.
170. Veenhuis, M. and Harder, W. 1987. Metabolic significance and biogenesis of microbodies in yeasts. In: Peroxisomes in Biology and Medicine. pp. 436-458. Fahimi, H. D. and Sies, H., Eds., Springer-Verlag, Berlin.
171. Veenhuis, M. and Harder, W. 1988. Microbodies in yeasts: structure, function and biogenesis. Microbiol. Sci., 5:347-351.
172. Veenhuis, M. and Harder, W. 1991. Microbodies. In: The Yeasts. vol. 4, pp. 601-653. Rose, A. H. and Harrison, J. S., Eds., Academic Press, London.
173. Veenhuis, M., Van Dijken, J. P., and Harder, W. 1983. The significance of peroxisomes in the metabolism of one-carbon compounds in yeasts. In: Advances in Microbial Physiology. vol. 24, pp. 1-82. Rose, A. H. and Wilkinson, J. F., Eds., Academic Press, London.
174. Veenhuis, M., Van der Klei, I. J., and Harder, W. 1986. Physiological role of microbodies in the yeast Trichosporon cutaneum during growth on ethylamine as the source of energy, carbon and nitrogen. Arch. Microbiol., 145:39-50.
175. Wang, T., Luo, Y., and Small, G. M. 1994. The POX1 gene encoding peroxisomal acyl-CoA oxidase in Saccharomyces cerevisiae is under the control of multiple regulatory elements. J. Biol. Chem., 269:24480-24485.
176. Wang, T. W., Lewin, A. S., and Small, G. M. 1992. A negative regulating element controlling transcription of the gene encoding acyl-CoA oxidase in Saccharomyces cerevisiae. Nucleic Acids Res., 20:3495-3500.
177. Wassef, M. K. 1977. Fungal lipids. Adv. Lipid Res., 15:159-232.
178. Waterham, H. R., Keizer-Gunnink, I., Goodman, J. M., Harder, W., and Veenhuis, M. 1992. Development of multipurpose peroxisomes in Candida boidinii grown in oleic acid-methanol limited continuous cultures. J. Bacteriol., 174:4057-4063.
179. Waterham, H. R., Titorenko, V. I., Swaving, G. J., Harder, W., and Veenhuis, M. 1993. Peroxisomes in the methylotrophic yeast Hansenula polymorpha do not necessarily derive from pre-existing organelles. EMBO J., 12:4785-4794.
180. Welsh, F. W., Murray, W. D., and Williams, R. E. 1989. Microbiological and enzymatic production of flavor and fragrance chemicals. Crit. Rev. Biotechnol., 9:105-169.
181. Wilson, G. N. 1991. Structure-function relationships in the peroxisome: implications for human disease. Biochem. Med. Metab. Biol., 46:288-298.
182. Wink, J., Voelskow, H., Grabley, S., and Deger, H. M. 1988. Pfirsich-Aroma, Verfahren zur Herstellung und seine Verwendung, European Patent 0.283.950.
183. Wurzenberger, M. and Grosch, W. 1982. The enzymic oxidative breakdown of linoleic acid in mushrooms. Z. Lebensm. Unters. Forsch., 175:186-190.
184. Zhang, J. W. and Lazarow, P. B. 1995. PEB1 (PAS7) in Saccharomyces cerevisiae encodes a hydrophilic, intra-peroxisomal protein that is a member of the WD repeat family and is essential for the import of thiolase into peroxisomes. J. Cell Biol., 129:65-80.
185. Zwart, K. B., Veenhuis, M., Plat, G., and Harder, W. 1983. Characterization of glyoxysomes in yeasts and their transformation into peroxisomes in response to changes in environmental conditions. Arch. Microbiol., 136:28-38.