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United States Patent (19) 11 Patent Number: 6,146,860 Asakura Et Al

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United States Patent (19) 11 Patent Number: 6,146,860 Asakura Et Al USOO6146860A United States Patent (19) 11 Patent Number: 6,146,860 Asakura et al. (45) Date of Patent: Nov. 14, 2000 54) MANUFACTURE OF L-ASCORBIC ACID Bublitz, et al., “The role of aldonolactonase in the conver AND D-ERYTHORBIC ACID sion of L-gulonate to L-ascorbate,” Biochimica et Bio physica, vol. 47, pp. 288-297 (1961). 75 Inventors: Akira Asakura, Fujisawa; Tatsuo Derwent English language abstract of De 196 04 798 A1 Hoshino, Kamakura; Tatsuya Kiyasu, (document B2). Fujisawa; Masako Shinjoh, Kamakura, Zachariou, et al., “Glucose-Fructose Oxidoreductase, a New all of Japan Enzyme Isolated from Zymomonas mobilis That is Respon sible for Sorbitol Production,” Journal of Bacteriology, 73 Assignee: Roche Vitamins Inc., Parsippany, N.J. 167(3): 863–869 (1986). Hucho, et al., “Glucono-6-Lactonase From Escherichia 21 Appl. No.: 09/484,966 Coli,” Biochimica et Biophysica Acta, 276:176-179 (1982). Shimizu, et al., “Purification and Characterization of a 22 Filed: Jan. 18, 2000 Novel Lactonohydrolase, Catalyzing the Hydrolysis of 30 Foreign Application Priority Data Aldonate Lactones and Aromatic Lactones, from Fusarium oxysporum,” Eur, J. Biochem., 209:383-390 (1992). Jan. 18, 1999 EP European Pat. Off. .............. 991OO785 Kanagasundaram, et al., “Isolation and Characterization of the gene encoding gluconolactonase from Zymomonas 51) Int. Cl." ............................... C12P 17/04; C12N 9/18 52 U.S. C. ... 435/126; 435/137; 435/195; mobilis,” Biochimica et Biophysica Acta, 1171: (1992). 435/196; 435/197 Primary Examiner Herbert J. Lilling 58 Field of Search ..................................... 435/126, 137, Attorney, Agent, or Firm Mark E. Waddell; Stephen M. 435/195, 196, 197 Haracz; Bryan Cave LLP 56) References Cited 57 ABSTRACT U.S. PATENT DOCUMENTS A process for producing L-ascorbic acid (vitamin C) from 4,259,443 3/1981 Danehy. 2-keto-L-gulonic acid or D-erythorbic acid from 2-keto-D- 5,817,490 10/1998 Hubbs ..................................... 435/137 gluconic acid by contacting 2-keto-L-gulonic acid or 2-keto 5,859,262 1/1999 Meir-Eyalet al. ..................... 435/126 D-gluconic acid, respectively, in Solution with a lactonase, particularly one belonging to the enzyme class EC 3.1.1.x, FOREIGN PATENT DOCUMENTS according to the classification of Enzyme Nomenclature. 196 O4798 The Solvent for this reaction can be water, an aqueous A1 8/1997 Germany. alcohol, a non-alcoholic organic Solvent or a mixture of an WO97/43433 11/1999 WIPO. aqueous alcohol and a non-alcoholic organic Solvent. The contacting is generally performed in a temperature range of OTHER PUBLICATIONS O C. to 120° C. and a pH range of 1.5 to 12. In each case Ogawa, et al., “Microbial enzymes: new industrial applica the Starting material can be in the form of the free acid, the tions from traditional screening methods,” TIBTECH, Vol. Sodium Salt, or the calcium Salt. The So-produced Vitamin C 17, pp. 13–20 (1999). has very well known uses, and the alternatively produced Kobayashi, et al., “Lactone-ring-cleaving enzyme: Genetic D-erythorbic acid is useful as an antioxidant for food analysis, novel RNA editing, and evolutionary implica additives. tions.” Proc. Natl. Acad. Sci. USA, vol. 95, pp. 12787–12792 (2998). 15 Claims, No Drawings 6,146,860 1 2 MANUFACTURE OF LASCORBIC ACID hydrolase Such as a protease, an esterase, a lipase or an AND D-ERYTHORBIC ACID amidase, WO 97/43433 exemplifies the formation of L-ascorbic acid from an ester of 2-keto-L-gulonic acid FIELD OF THE INVENTION (butyl 2-keto-L-gulonate), but no apparent formation of The present invention relates to a novel process for L-ascorbic acid from 2-keto-L-gulonic acid itself. WO producing L-ascorbic acid (vitamin C) or D-erythorbic acid 97/43433 discloses, for example, that Candida antartica B from 2-keto-L-gulonic acid or 2-keto-D-gluconic acid, lipase catalyzed the reaction to form 413-530 mg/l of respectively, using a lactonase. methyl 2-keto-L-gulonate, but no L-ascorbic acid, from 1% 2-keto-L-gulonic acid in the presence of 8.6% methanol at BACKGROUND OF THE INVENTION pH 3.1-3.2 at 38 C. Ester synthetic activity of Candida antartica B lipase on 2-keto-L-gulonic acid, an O-keto L-ascorbic acid has been produced from 2-keto-L-gulonic carboxylic acid, at acidic pH is apparently positive, but acid by the well-known Reichstein method (Helv. Chim. Acta 17, 311-328 (1934)). The method has been used intramolecular ester formation by this lipase was negligible. commercially for more than 60 years with many chemical It does not disclose a lactonase as the hydrolase enzyme and technical modifications to improve the efficiency of each 15 catalyst for the purpose of producing L-ascorbic acid from of the Steps to the compounds D-glucose, D-Sorbitol, 2-keto-L-gulonic acid. L-Sorbose, diacetone-L-Sorbose, diacetone-2-keto-L- Surprisingly, it has now been found that the conversion of gulonic acid, 2-keto-L-gulonic acid, and methyl 2-keto-L- 2-keto-L-gulonic acid to L-ascorbic acid can be performed gulonate, and L-ascorbic acid. In this process, the conver by a lactonase enzyme. Accordingly, it has been Surprising sion of D-Sorbitol to L-Sorbose is the sole microbial step, the found that the Selectivity of lactonase on cyclic esters is others being chemical Steps. The conversion of diacetone favorable for the production of L-ascorbic acid from 2-keto 2-keto-L-gulonic acid into L-ascorbic acid is achieved by L-gulonic acid. two different procedures: 1) deprotection to give 2-keto-L- Many kinds of lactonases are known, including glucono gulonic acid, followed by esterification with methanol and lactonase (EC 3.1.1.17) of Escherichia coli (F. Hucho et al., base-catalyzed cyclization; and 2) acid-catalyzed cyclization 25 Biochem. Biophys. Acta 276, 176-179 (1972)) or of to L-ascorbic acid directly from the protected or deprotected Zymomonas mobilis (M. Zachariou et al., J. Bacteriol. 167, 2-keto-L-gulonic acid. The Starting material for base 863–869 (1986) and V. Kanagasundaram et al., Biochem. catalyzed reactions is methyl 2-keto-L-gulonate, itself pre Biophys. Acta 1171, 198-200 (1992)), and lactonohydrolase pared by treatment of the acid with acidic methanol. An of Fusarium oxysporum (S. Shimizu et al., Eur. J. Biochem. alternative reaction of the methyl ester with sodium bicar 209, 383-390 (1992)). Further reported lactonases include bonate or Sodium acetate produces Sodium L-ascorbate. L-arabino no lacto nase (EC 3.1.1.15) and Many chemical and technical modifications have improved D-arabinonolactonase (EC 3.1.1.30) of Pseudomonas the efficiency of each Step, enabling the multistep synthesis Saccharophilia, L-rhamnono-1,4-lactonase (EC 3.1.1.65) of to remain the principally used and economical process. Pullularea pullulans, xylono-1,4-lactonase (EC 3.1.1.68) of D-Erythorbic acid has been produced from D-glucose via 35 Pseudomonas fragi and Gluconobacter Oxydans, cellobino 2-keto-D-gluconic acid, which itself can be produced by lactonase of Trichoderma reesei (Chem.-Zig. 113, 122–124 fermentation with a Strain belonging to the genus (1989)), 1.4-lactonase (EC 3.1.1.25), and lactonases with the Pseudomonas, and methyl 2-keto-D-gluconate. EC numbers 3.1.1.19, 3.1.1.24, 3.1.1.27, 3.1.1.36, 3.1.1.37, 3.1.1.38, 3.1.1.39, 3.1.1.45, 3.1.1.46, and 3.1.1.57. D-Erythorbic acid is mainly used as an antioxidant for food 40 additives. Among the lactonases, the lactonohydrolase of Fusarium Much time and effort has been devoted to finding other Oxysporum has been developed for the industrial asymmetric methods of Synthesizing L-ascorbic acid by microorgan hydrolysis of D-pantoyl lactone (K. Sakamoto et al., U.S. isms. Most microbial productions of L-ascorbic acid have Pat. No. 5,275,949). The enzyme catalyzes the hydrolysis of been focused on the production of an intermediate of 45 a relatively broad range of lactone compounds, including L-ascorbic acid production, 2-keto-L-gulonic acid, from D-pantoyl lactone and Several aldonolactones, e.g. L-Sorbose (G. Z. Yin et al., Wei Sheng Wu Hsueh Pao. 20, D-glucono-6-lactone and D-galactono-y-lactone, and the 246-251 (1980); A. Fujiwara et al., EP213591 (Roche); T. reverse reaction, lactonization. Hoshino et al., U.S. Pat. No. 4,960,695 (Roche); and I. H. Nucleotide Sequences are available for the genes of Some Nogami et al., EP221707), from D-Sorbitol (A. Fujiwara et 50 lactonases, i.e., the gluconolactonase gene of Zymomonas al., EP 213 591 (Roche); T. Hoshino et al., U.S. Pat. No. mobilis (960 bp; 320 amino acid residues; V. Kana 5,312,741 (Roche); M. Niwa et al., WO95/23220; and S. F. gasundaram et al., Biochem. Biophys. Acta 1171, 198-200 Stoddard et al., WO 98/17819), or from D-glucose via (1992)) and the lactonohydrolase gene of Fusarium 2,5-diketogluconic acid with a single, mixed or recombinant Oxysporum (1,140 bp; 380 amino acid residues; K. Saka culture (T. Sonoyama et al., Appl. Environ. Microbiol. 43, 55 moto et al., WO 97/10341). 1064-1069 (1982); and S. Anderson et al., Science 230, 144-149 (1985)). The 2-keto-L-gulonic acid can then be DETAILED DESCRIPTION OF THE converted into L-ascorbic acid by chemical means as INVENTION described above. Accordingly, the present invention provides a process for The involvement of an enzymatic proceSS for the conver 60 producing L-ascorbic acid from 2-keto-L-gulonic acid, and Sion of the 2-keto-L-gulonic acid ester into L-ascorbic acid also a process for producing D-erythorbic acid from 2-keto has recently been reported (J.
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