The biotechnological potential of the al-2 gene from Neurospra crassa for the production of monocyclic keto hydroxy carotenoids

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1761, Issue 9, 2006, Pages 1085-1092

  Sandmann, Gerhard ^a   Zhu, Changfu ^a   Krubasik, Philipp ^a   Fraser, Paul D ^b  

^a GOETHE UNIVERSITY   (Germany)

^b UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Gene al 2; Hydroxylated 4 keto carotene derivatives; Hydroxylated 4 keto torulene derivatives; Lycopene cyclase CrtYB; Phytoene synthase; Phytoene synthase cDNA

Indexed keywords

2 HYDROXY 4 KETO GAMMA CAROTENE; 2 HYDROXY 4 KETO TORULENE; 3 HYDROXY 4 KETO GAMMA CAROTENE; 3 HYDROXY 4 KETO TORULENE; 3,1' DIHYDROXY 4 KETO GAMMA CAROTENE; 4 KETO 1' HYDROXY GAMMA CAROTENE; CAROTENOID; COMPLEMENTARY DNA; FUNGAL ENZYME; GAMMA CAROTENE; LYCOPENE CYCLASE; PHYTOENE SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG;

AL 2 GENE; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; CYCLIZATION; ENZYME ACTIVITY; ESCHERICHIA COLI; FUNGAL GENE; FUNGUS; GENE EXPRESSION; MOLECULAR CLONING; NEUROSPRA CRASSA; NONHUMAN; PRIORITY JOURNAL;

ALKYL AND ARYL TRANSFERASES; CAROTENOIDS; CLONING, MOLECULAR; ESCHERICHIA COLI; FUNGAL PROTEINS; INTRAMOLECULAR LYASES; KETONES; NEUROSPORA CRASSA;

ESCHERICHIA COLI; NEUROSPORA CRASSA;

EID: 33748471772     PISSN: 13881981     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbalip.2006.06.002     Document Type: Article

References (43)

1. Mayne S.T. Beta-carotene, carotenoids, and disease prevention in humans. FASEB J. 10 (1996) 690-701
2. Britton G., Liaaen-Jensen S., and Pfander H. Carotenoids Handbook (2004), Birkhäuser Verlag, Basel
3. Bernhard K. Synthetic astaxanthin, the route of a carotenoid from research to commercialization. In: Krinsky N.I., Mathews-Roth M.M., and Taylor R.F. (Eds). Carotenoids Chemistry and Biology (1987), Plenum Press, New York 337-363
4. Nonomura A.M. Industrial biosynthesis of carotenoids. In: Krinsky N.I., Mathews-Roth M.M., and Taylor R.F. (Eds). Carotenoids Chemistry and Biology (1987), Plenum Press, New York 365-375
5. Sandmann G. Carotenoid biosynthesis and biotechnological application. Arch. Biochem. Biophys. 385 (2001) 4-12
6. Takaichi S., Tsuji K., Matsuura K., and Shimada K. A monocyclic carotenoid glucoside ester is the major carotenoid in the green filamentous bacterium Chloroflexus aurantiacus. Plant Cell Physiol. 36 (1995) 773-778
7. Reichenbach H., and Kleinig H. The carotenoids of Myxococcus fulvus (Myxobacterales). Arch. Microbiol. 76 (1971) 364-380
8. Tao L., Picataggio S., Rouviere P.E., and Cheng Q. Asymmetrically acting lycopene β-cyclases (CrtLm) from non-photosynthetic bacteria. Mol. Genet. Gen. 271 (2004) 180-188
9. Schmidt K., and Schiburr R. The carotenoids of the green sulphur bacteria: carotenoid composition in 18 strains. Arch. Microbiol. 74 (1970) 350-355
10. Albrecht M., Takaichi S., Misawa N., Schnurr G., Böger P., and Sandmann G. Synthesis of atypical cyclic and acyclic hydroxy carotenoids in Escherichia coli transformants. J. Biotechnol. 58 (1997) 177-185
11. Albrecht M., Takaichi S., Steiger S., Wang Z.Y., and Sandmann G. Novel hydroxycarotenoids with improved antioxidative properties produced by gene combination in Escherichia coli. Nat. Biotechnol. 18 (2000) 843-846
12. Teramoto M., Takaichi S., Inomata Y., Ikenaga H., and Misawa N. Structural and functional analysis of a lycopene beta-monocyclase gene isolated from a unique marine bacterium that produces myxol. FEBS Lett. 545 (2003) 120-126
13. Sandmann G., and Misawa N. Fungal carotenoids. In: Osiewacz H.D. (Ed). The Mycota X: Industrial Applications (2002), Springer Verlag, Berlin 247-262
14. Emerson R., and Fox D.L. γ-carotene in the sexual phase of the aquatic fungus Allomyces. Proc. Royal Soc. 128B (1940) 275-293
15. Aasen A.J., and Liaaen-Jensen S. Fungal Carotenoids II. The structure of the carotenoid acid neurosporaxanthin. Acta Chem. Scan. 19 (1965) 1843-1853
16. Harding R.W., Huang P.C., and Mitchell H.K. Photochemical studies of the carotenoid biosynthetic pathway in Neurospora crassa. Arch. Biochem. Biophys. 129 (1969) 696-707
17. Liu I.-S., Lee T.H., Yokoyama H., Simpson K.L., and Chichester C.O. Isolation and identification of 2-hydroxyplectaniaxanthin from Rhodotorula aurantiaca. Phytochem 12 (1973) 2953-2956
18. Sandmann G., Albrecht M., Schnurr G., Knörzer O., and Böger P. The biotechnological potential and design of novel carotenoids by gene combination in Escherichia coli. Trends Biotechnol. 17 (1999) 233-237
19. Schmidhauser T.J., Lauter F.-R., Schuhmacher M., Zhou W., Russo V.E.A., and Yanofsky C. Characterization of al-2, the phytoene synthase gene of Neurospora crassa. Cloning, sequence analysis and photoregulation. J. Biol. Chem. 269 (1994) 12060-12066
20. Lee P.C., Mijts B.N., and Schmidt-Dannert C. Investigation of factors influencing production of the monocyclic carotenoid torulene in metabolically engineered Escherichia coli. Appl. Microbiol. Biotechnol. 65 (2004) 538-546
21. Kovach M., Elzer P., and Hill D.S. Four new derivatives of the broad-host range cloning vector pBBR1MCS, carrying different antibiotic resistance cassettes. Gene 166 (1994) 175-176
22. Borovkov A.Y., and Rivkin M.I. XcmI-containing vector for direct cloning of PCR products. BioTechniques 22 (1997) 812-814
23. Misawa N., Satomi Y., Kondo K., Yokoyama A., Kajiwara S., Saito T., Ohtani T., and Miki W. Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level. J. Bacteriol. 177 (1995) 6575-6584
24. Hausmann A., and Sandmann G. A single five-step desaturase is involved in the carotenoid biosynthesis pathway to β-carotene and torulene in Neurospora crassa. Fungal Genet. Biol. 30 (2000) 147-153
25. Ruther A., Misawa N., Böger P., and Sandmann G. Production of zeaxanthin in Escherichia coli transformed with different carotenogenic plasmids. Appl, Microbiol. Biotechnol. 48 (1997) 162-167
26. Sambrook J., Fritsch E.F., and Maniatis T. Molecular Cloning, A Laboratory Manual. 2nd ed. (1989), Cold Spring Harbour Laboratory Press, New York
27. Davies B.H. Carotenoids. In: Goodwin T.W. (Ed). Chemistry of Plant Pigments (1976), Academic Press, London
28. Eugster C.H. Chemical derivatization: microsomale tests for the presence of common functional groups in carotenoids. In: Britton G., Liaaen-Jensen S., and Pfander H. (Eds). Carotenoid Volume 1 A Isolation and Analysis (1995), Birkhäuser Verlag, Basel 71-80
29. Verdoes J.C., Krubasik K.P., Sandmann G., and van Ooyen A.J. Isolation and functional characterisation of a novel type of carotenoid biosynthetic gene from Xanthophyllomyces dendrorhous. Mol. Gen. Genet. 262 (1999) 453-461
30. Armstrong G.A., Alberti M., Leach F., and Hearst J.E. Nucleotide sequence, organization and nature of the protein products of the carotenoid biosynthesis gene cluster of Rhodobacter capsulatus. Mol. Gen. Genet. 216 (1989) 254-268
31. Nishida Y., Adachi K., Kasai H., Shizuri Y., Shindo K., Sawabe A., Komemushi S., Miki W., and Misawa N. Elucidation of a carotenoid biosynthesis gene cluster encoding a novel enzyme, 2,2′-beta-hydroxylase, from Brevundimonas sp. strain SD 212 and combinatorial biosynthesis of new or rare xantophylls. Appl. Environ. Microbiol. 71 (2005) 4286-4296
32. Misawa N., Nakagawa M., Kobayashi K., Yamano S., Izawa Y., Nakamura K., and Harashima K. Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli. J. Bacteriol. 172 (1990) 6704-6712
33. Breitenbach J., Misawa N., Kajiwara S., and Sandmann G. Expression in Escherichia coli and properties of the carotene ketolase from Haematococcus pluvialis. FEMS Microbiol. Lett. 140 (1996) 241-246
34. Sandmann G. Combinatorial biosynthesis of carotenoids in a heterologous host: a powerful approach for the biosynthesis of novel structures. ChemBiochem 3 (2002) 629-635
35. Lee P.C., Momen A.Z., Mijts B.N., and Schmidt-Dannert C. Biosynthesis of structurally novel carotenoids in Escherichia coli. Chem. Biol. 10 (2003) 453-462
36. Raisig A., Bartley G., Scolnik P., and Sandmann G. Purification in an active state and properties of the 3-step phytoen desaturase from Rhodobacter capsulata after overexpression in Escherichia coli. J. Biochem. 119 (1996) 559-564
37. Sandmann G. Molecular evolution of carotenoid biosynthesis from bacteria to plants. Physiol. Plant. 116 (2002) 431-440
38. Fiasson J., Arpin N., and Perrier J. 4-Keto-γ-carotene (β,ψ-caroten-4-one), the major pigment of an Arthrobacter sp. Can. J. Biochem. 54 (1976) 1016-1017
39. Kleinig H., Meister W., and Englert G. Carotenoids of rhizomania, II. The effect of nicotine on the carotenoid-pattern of Rhizobium lupini. Arch. Microbiol. (1978) 71-74
40. Andrewes A.G., Phaff H., and Starr M.P. Carotenoids of Phaffia rhodozyma, a red-pigmented fermenting yeast. Phytochem. 15 (1976) 1003-1007
41. Albrecht M., Misawa N., and Sandmann G. Metabolic engineering of the terpenoid biosynthetic pathway of Escherichia coli for production of the carotenoids β-carotene and zeaxanthin. Biotechn. Lett. 21 (1999) 791-795
42. Fraser P.D., Shimada H., and Misawa N. Enzymic confirmation of reactions involved in routes to astaxanthin formation, elucidated using a direct substrate in vitro assay. Eur. J. Biochem. 252 (1998) 229-236
43. Albrecht M., Steiger S., and Sandmann G. Expression of a ketolase gene mediates the synthesis of canthaxanthin in Synechococcus leading to resistance against pigment photodegradation and UV-B sensitivity of photosynthesis. Photochem. Photobiol. 73 (2001) 551-555