P450 oxygenases and methods of use

Chemistry: molecular biology and microbiology – Enzyme – proenzyme; compositions thereof; process for... – Oxidoreductase

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C435S004000, C435S006120, C435S025000, C435S069100, C435S071100, C435S132000, C435S252300, C435S320100, C435S440000, C536S023200

Reexamination Certificate

active

07402417

ABSTRACT:
This disclosure provides the nucleic acid and protein sequences of novel P450 oxygenases that utilize, at least, taxoid substrates, including taxadiene isomers. The disclosed oxygenases, such as a taxoid 5α-hydroxylase, hydroxylate, at least, the C5 position of a taxoid. Also provided are methods of introducing oxygen at the C5 position of a taxoid and methods of producing the anti-cancer drug, paclitaxel (also known as Taxol™), and other taxoids, such as paclitaxel intermediates.

REFERENCES:
patent: 6043072 (2000-03-01), Croteau et al.
patent: 6787343 (2004-09-01), Croteau et al.
patent: 7005283 (2006-02-01), Croteau et al.
patent: WO 98/40470 (1998-09-01), None
patent: WO 01/34780 (2001-05-01), None
Branden et al. Introduction to Protein Structure, Garland Publishing Inc., New York, p. 247, 1991.
Guo et al. Proc Natl Acad Sci USA. Jun. 22, 2004;101(25):9205-10.
Meinkoth et al. Anal. Biochem. 138, 26 (1984).
Cabello-Hurtado et al., “Cloning, Expression in Yeast, and Functional Characterization of CYP81B1, a Plant Cytochrome P450 That Catalyzes In-chain Hydroxylation of Fatty Acid,”J. Biol. Chem., 273(13):7260-7267, 1998.
Chau and Croteau, “Molecular cloning and characterization of a cytochrome P450 taxoid 2α-hydroxylase involved in Taxol biosynthesis,”Arch. Biochem. Biophys., 427:48-57, 2004.
Chau et al., “Taxol Biosynthesis: Molecular Cloning and Characterization of a Cytochrome P450 Taxoid 7β-Hydroxylase,”Chem. Biol., 11:663-672, 2004.
Chau, “Molecular Cloning and Characterization of Three Enzymes Involved in Taxol/Taxoid Biosynthesis: Taxoid 2α-Hydroxylase, Taxoid 7β-Hydroxylase, and Taxoid 5α-O-Acetyltransferase,” Ph.D. Dissertation, Pullman, WA:Washington State University, May 2004.
Eisenreich et al., “Multiple Oxygenase Reactions in the Biosynthesis of Taxoids,”J. Am. Chem. Soc., 120:9694-9695, 1998.
Fischer et al., “Towards molecular farming in the future: using plant-cell-suspension cultures as bioreactors,”Biotechnol. Appl. Biochem., 30:109-112, 1999.
Hefner et al., “Cytochrome P450-catalyzed hydroxylation of taxa-4(5),11(12)-diene to taxa-4(20),11(12)-dien-5α-ol: the first oxygenation step in taxol biosynthesis,”Chem. Biol., 3:479-489, 1996.
Hefner et al., “Cloning and Functional Expression of a cDNA Encoding Geranylgeranyl Diphosphate Synthase fromTaxus canadensisand Assessment of the Role of this Prenyltransferase in Cells Induced for Taxol Production,”Arch. Biochem. Biophys., 360(1):62-74, 1998.
Jennewein et al., “Taxol biosynthesis: Taxane 13α-hydroxylase is a cytochrome P450-dependent monooxygenase,”Proc. Natl. Acad. Sci. USA, 98(24):13595-13600, 2001.
Jennewein et al., “Taxoid metabolism: Taxoid 14beta-hydroxylase is a cytochrome P450-dependent monooxygenase,”Arch. Biochem. Biophys., 413(2):262-270, 2003 (Abstract).
Jennewein et al., “Cytochrome p450 taxadiene 5alpha-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis,”Chem Biol., 11(3):378-387, 2004.
Jennewein et al., “Random sequencing of an inducedTaxuscell cDNA library for identification of clones involved in Taxol biosynthesis,”Proc. Natl. Acad. Sci. USA, 101(24):9149-9154, 2004.
Nielson et al., “Cytochrome P450s in Plants,” In:Cytochrome P450: Structure, Mechanism, and Biochemistry, Chap. 12, 3rd ed., ed. by Ortiz de Montellano, New York, NY:Kluwer Academic/Plenum Publishers, 2005.
Pauli and Kutchan., “Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcoclaurine 3′-hydroxylase (CYP80B1), a new methyl jasmonate-inducible cytochrome P-450-dependent mono-oxygenase P-450-dependent mono-oxygenase of benzylisoquinoline alkaloid biosynethesis,”Plant J., 13(6):793-801, 1998.
Schoendorf et al., “Molecular cloning of a cytochrome P450 taxane 10β-hydroxylase cDNA fromTaxusand functional expression in yeast,”Proc. Natl. Acad. Sci. USA, 98(4):1501-1506, 2001.
Schopfer and Ebel, “Identification of elicitor-induced cytochrome P450s of soybean (Glycine maxL.) using differential display of mRNA,”Mol. Gen. Genet., 258:315-322, 1998.
Wildung et al., “A cDNA Clone for Taxadiene Synthase, the Diterpene Cyclase That Catalyzes the Committed Step of Taxol Biosynthesis,”J. Biol. Chem., 271(16):9201-9204, 1996.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

P450 oxygenases and methods of use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with P450 oxygenases and methods of use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and P450 oxygenases and methods of use will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2802073

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.