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(12) United States Patent (10) Patent No.: US 7,863,014 B2 Kawai Et Al

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(12) United States Patent (10) Patent No.: US 7,863,014 B2 Kawai Et Al USOO7863 014B2 (12) United States Patent (10) Patent No.: US 7,863,014 B2 Kawai et al. (45) Date of Patent: Jan. 4, 2011 (54) PROCESS FOR PREPARING NICOTINAMIDE Beutler et al., “Coenzymes, metabolites, and other biochemical ADENNE ONUCLEOTDE reagents', pp. 328-393. In Bergmeyer, H.U. (ed.), Methods of enzy PHOSPHATEONADP) matic analysis, vol. 1, Verlag Chemie, Weinheim (1983). Matsushita et al. “NADP production using thermostableNAD kinase (75) Inventors: Shigeyuki Kawai, Kyoto (JP): Kousaku of Corynebacterium flaccumfaciens AHU-1622. Can. J. Microbiol. Murata, Kyoto (JP); Hirokazu vol. 32, 1986, pp. 585-590. Matsukawa, Tokyo (JP); Shoichi McGuinness et al., “NAD Kinase—A Review'. Int. J. Biochem., vol. Tomisako, Tokyo (JP); Yoshio Ando, 17, No. 1, pp. 1-11, 1985. Tokyo (JP); Yuhsi Matsuo, Tokyo (JP) Murata et al., “Continuous Production of NADP by Immobilized Brevibacterium ammoniagenes Cells'. Biotechnology and (73) Assignee: Oriental Yeast Co., Ltd., Tokyo (JP) Bioengineering, vol. XXI, pp. 887-895 (1979). Murata et al., “Metaphosphate: A New Phosphoryl Donor for NAD (*) Notice: Subject to any disclaimer, the term of this Phosphorylation'. Agric. Biol. Chem., 44(1), 61-68, 1980. patent is extended or adjusted under 35 Wood etal, "Biological Aspects of Inorganic Polyphosphates'. Ann. U.S.C. 154(b) by 516 days. Rev. Biochem. 1988, 57:235-260. Kawai et al., “Inorganic Polyphosphate/ATP-NAD Kinase of (21) Appl. No.: 10/482,791 Micrococcus flavus and Mycobacterium tuberculosis H37Rv”, Bio chemical and Biophysical Research Communications, 276, 57-63 (22) PCT Filed: Jul. 2, 2002 (2000). Ausubel et al. “Current Protocols in Molecular Biology”, John (86). PCT No.: PCT/PO2AO6692 Wiley & Sons, Inc., New York (1994). Bradford etal, "A Rapid and Sensitive Method for the Quantitation of S371 (c)(1), Microgram Quantities of Protein Utilizing the Principle of Protein (2), (4) Date: Jul. 20, 2004 Dye Binding”. Analytical Biochemistry 72,248-254 (1976). Chibata et al., “Immobilized Aspartase-Containing Microbial Cells: (87) PCT Pub. No.: WO03/004654 Preparation and Enzymatic Properties”. Applied Microbiology, May 1974, vol. 27, No. 5, pp. 878-885. PCT Pub. Date: Jan. 16, 2003 Murata et al., “Continuous Production of Glucose-6-phosphate by Immobilized Achromobacter butyri Cells”, European J. Appl. (65) Prior Publication Data Microbiol. Biotechnol. 7, 45-51 (1979). US 2004/0248263 A1 Dec. 9, 2004 Fiske et al. “The Colorimetric Determination of Phosphorus'. The Journal of Biological Chemistry, vol. 66, No. 2, pp. 375-400 (1925). (30) Foreign Application Priority Data Langer et al., “Enzymatic Regeneration of ATP, AIChE Journal, Nov. 1976, vol. 22, No. 6, pp. 1079-1090. Jul. 2, 2001 (JP) ............................. 2001-2O1400 Maruyama et al., “ATP Production from Adenine by a Self-coupling Enzymatic Process: High-level Accumulation under Ammonium (51) Int. Cl. limited Conditions'. Biosci. Biotechnol. Biochem, 65(3), 644-650, CI2P I/O (2006.01) 2001. (52) U.S. Cl. ........................................................ 435/41 Fujio et al. Enzymatic Production of Pyrimidine Nucleotides Using (58) Field of Classification Search .................... 435/90 Corynebacterium ammoniagenes Cells and Recombinant See application file for complete search history. Escherichia coli Cells: Enzymatic Production of CDP-Choline from Orotic Acid and Choline Chloride (Part I), Biosci. Biotech. (56) References Cited Biochem. 61(6), 956-959, 1997. Kawai et al., “Molecular characterization of Escherichia coli NAD FOREIGN PATENT DOCUMENTS kinase”, Eur, J. Biochem. 268, 4359-4365 (2001). JP 52-82792 7/1977 (Continued) OTHER PUBLICATIONS Primary Examiner Sheridan Swope Kawai et al., Biochem. Biophys. Res. Commun. 2000, vol. 276, No. (74) Attorney, Agent, or Firm Nixon & Vanderhye P.C. 1, p. 57-63.* Ngo et al. in The Protein Folding Problem and Tertiary Structure (57) ABSTRACT Prediction, 1994, Merz et al. (ed.), Birkhauser, Boston, MA, pp. 433 and 492-495, Ref. U, Form-892.* Zerez et al. Negative modulation of Escherichia coli NAD kinase by NADPH and NADH.J Bacteriol. Jan. 1987; 169(1): 184-8.* The present invention provides a novel process for preparing USPTO in house BLAST alignment of SEQ ID No. 1 with PIR nicotinamide adenine dinucleotide phosphate (NADP). The database F70502 and UniProt database POASS6. process of the present invention comprises performing phos Labesse etal, Diacylglyceride kinases, sphingosine kinases and NAD phorylation using a polyphosphoric acid or a salt thereof and kinases: distant relatives of 6-phosphofructokinases. Trends nicotinamide adenine dinucleotide (NAD") as substrates in Biochem Sci. Jun. 2002:27(6):273-5. Review.* the presence of a polyphosphate-dependent NAD" kinase Kawai et al. “Establishment of Mass-Production System for NADP from a Mycobacterium, wherein the reaction solution con Using Bacterial Inorganic Polyphosphate/ATP-NAD Kinase'. J. tains 0.1-15% by weight of the polyphosphoric acid or a salt Biosci. Bioeng. Dec. 2001, vol. 92, No. 5, pp. 447-452. Kawai et al., “Inorganic Polyphosphate/ATP-NAD Kinase of thereof, and 5-150 mM of a divalent metalion. Micrococcus flavus and Mycobacterium tuberculosis H37Rv'. Biochem. Biophys. Res. Commun. 2000, vol. 276, No. 1, pp. 57-63. 8 Claims, 7 Drawing Sheets US 7,863,014 B2 Page 2 OTHER PUBLICATIONS calmodulin-dependent NAD+ kinase” (as summarized from http:// www.brenda-enzymes.info/literature/lit.php4?e=2.7.1.23&r= Kawaietal, “Molecular cloning and identification of UTRI of a yeast 641199 retrieved Sep. 14, 2009). Saccharomyces cerevisiae as a gene encoding an NAD kinase'. Williams, M.B.Arch. Biochem. Biophys. 237, 80-87 (1985) FEMS Microbiology Letters, vol. 200 No. 2, (2001), 181-184. "Calmodulin-dependent NAD kinase of human neutrophils' Waehneldt et al., “Phosphorylation of Nucleosides with (Abstract only). Polyphosphoric Acid'. Biochem. Biophys. Acta, 134 (1967), 1-8. Ji. X. etal Ann. N.Y. Acad. Sci. 434, 264-266 (1984) “Immobilization Cole et al. "Deciphering the biology of Mycobacterium tuberculosis of NAD kinase” (Abstract only). from the complete genome sequence”. Nature, vol. 393, Jun. 1998, Muto, S. Z. Pflanzenphysiol. 109,385-393 (1983) “Kinetic nature of 537-544. calmodulin-dependent NAD kinase from pea seedlings' (as Summa “Enzyme Handbook”, 1983, Asakura Publishing, p. 339. rized from http://www.brenda-enzymes.info/literature/lit.php4?e=2. Schoner et al., “Enhanced Translational Efficiency with Two-Cistron Expression System'. Methods in Enzymology, vol. 185, 94-103 7.1.23&r=641200 retrieved Sep. 14, 2009). (1990). Tseng, Y.Metal Biochim. Biophys. Acta 568, 205-214 (1979) “Iso Suzuki et al. “Organization of rRNA Genes in Mycobacterium bovis lation and characterization of yeast nicotinamide adenine BCG”. Journal of Bacteriology, Feb. 1987, vol. 169, No. 2, pp. dinucleotide kinase” (Abstract only). 839-843. Kawai S et al Biochem Biophys Res Commun. Sep. 16. Patent Abstracts of Japan, Publication No. 52-082792, published 2000:276(1):57-63 “Inorganic Polyphosphate/ATP-NAD kinase of Nov. 7, 1977. Applicant Tanabe Seiyaku COLTD, Inventor: Senhata Micrococcus flavus and Mycobacterium tuberculosis H37RV.” Ichiro et al. Title: Preparation of Nicotinamide-Adenine (Abstract only). Dinucleotide Phosphate (Abstract only). Chung, A.E.; J. Biol. Chem. 242, 1182-1186 (1967) “Nicotinamide Filippovich et al., “ATP- and Polyphosphate-dependent Bacterial adenine dinucleotide kinase from Azotobacter vinelandii. I. Purifi NAD" Kinases”. Prikladnaya Biokhimiya i Mikrobiologiya, vol. 36, cation and properties of the enzyme'. No. 2 (2000), p. 117-121 (with English abstract). Zerez et al. Arch Microbiol. May 1986; 144(4):313-6 “NAD kinase Zerez et al. Arch Microbiol. May 1986; 144(4):313-6 “NAD kinase from Bacillus licheniformis: inhibition by NADP and other proper from Bacillus licheniformis: inhibition by NADP and other proper ties. ties” (Abstract only). Raffaelli, Netal, Biochemistry 43, 7610-7617 (2004) “Character Kawaietal, Eur J. Biochem. Aug. 2001:268(15):4359-65 “Molecular ization of Mycobacterium tuberculosis NAD kinase: functional characterization of Escherichia coli NAD kinase.” analysis of the full-length enzyme by site-directed mutagenesis'. Garavaglia, S et al J. Bacteriol. 185, 4844-4850 (2003) 'Allosteric Ochiai, Aetal Protein Expr. Purif.36, 124-130 (2004) “Overexpres regulation of Bacillus subtilis NAD kinase by quinolinic acid”. sion, purification, and characterization of ATP-NAD kinase of Raffaelli, Netal, Biochemistry 43, 7610-7617 (2004) “Character Sphingomonas sp. Al”. ization of Mycobacterium tuberculosis NAD kinase: functional Kawai, Set al J. Biol. Chem. 280, 39200-39207 (2005) “MJO917 in analysis of the full-length enzyme by site-directed mutagenesis” archaeon Methanococcus jannaschii is a novel NADP phosphatase? (Abstract only). NAD kinase. Ochiai, Aetal Protein Expr. Purif.36, 124-130 (2004) “Overexpres Lerner, Fetal Biochem. Biophys. Res. Commun. 288, 69-74 (2001) sion, purification, and characterization of ATP-NAD kinase of "Structural and functional characterization of human NAD kinase'. Sphingomonas sp. Al” (Abstract only). Delumeau, O. et al Plant Sci. 138, 43-52 (1998) “NAD+ kinase Kawai, Set al J. Biol. Chem. 280, 39200-39207 (2005) “MJO917 in activity, calmodulin levels during the growth of isolated cells from archaeon Methanococcus jannaschii is a novel NADP phosphatase? Lycopersicon pimpinellifolium and kinetic constants of the NAD kinase” (Abstract only). calmodulin-dependent NAD+ kinase”. Lerner, Fetal Biochem. Biophys. Res. Commun. 288, 69-74
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