A single and two step isomerization process for D-tagatose and L-ribose bioproduction using L-arabinose isomerase and D-lyxose isomerase

Enzyme and Microbial Technology

Volumn 97, Issue , 2017, Pages 27-33

  Patel, Manisha J ^a   Akhani, Rekha C ^a   Patel, Arti T ^a   Dedania, Samir R ^a   Patel, Darshan H ^a,b  

^a CHAROTAR UNIVERSITY OF SCIENCE AND TECHNOLOGY   (India)

^b CHAROTAR UNIVERSITY OF SCIENCE AND TECHNOLOGY   (India)

Author keywords

D Tagatose; L arabinose isomerase; L Ribose; Shigella flexneri; Two step isomerization

Indexed keywords

CLONING; ESCHERICHIA COLI; ISOMERIZATION; SUGARS;

BIOCHEMICAL CHARACTERIZATION; CONVERSION RATES; D-LYXOSE ISOMERASE; D-TAGATOSE; ITS EFFICIENCIES; L-ARABINOSE ISOMERASE; L-RIBOSE; SHIGELLA FLEXNERI;

ISOMERS;

D LYXOSE ISOMERASE; ISOMERASE; L ARABINOSE ISOMERASE; L RIBOSE; MONOSACCHARIDE; RIBOSE; TAGATOSE; UNCLASSIFIED DRUG; ARABINOSE; D-LYXOSE KETOL-ISOMERASE; GALACTOSE; HEXOSE; L-ARABINOSE ISOMERASE; RECOMBINANT PROTEIN;

ARTICLE; BIOTRANSFORMATION; CARBOHYDRATE SYNTHESIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME KINETICS; ESCHERICHIA COLI; GENE EXPRESSION; ISOMERIZATION; NONHUMAN; SHIGELLA FLEXNERI; THERMOSTABILITY; BACILLALES; BACTERIAL GENE; BIOSYNTHESIS; BIOTECHNOLOGY; CHEMISTRY; ENZYME STABILITY; ENZYMOLOGY; GENETICS; KINETICS; METABOLISM; MOLECULAR CLONING; STEREOISOMERISM;

ALDOSE-KETOSE ISOMERASES; ARABINOSE; BACILLALES; BIOTECHNOLOGY; CLONING, MOLECULAR; ENZYME STABILITY; GALACTOSE; GENES, BACTERIAL; HEXOSES; KINETICS; RECOMBINANT PROTEINS; RIBOSE; SHIGELLA FLEXNERI; STEREOISOMERISM;

EID: 84995555383     PISSN: 01410229     EISSN: 18790909     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2016.11.001     Document Type: Article

References (51)

1. [1] Levin, G.V., Zelmer, L.R., Saunders, J.P., Beadle, J.R., Sugar substitutes: their energy values, and potential health bulk characteristics. Am. Soc. Clin. Nutr. 62 (1995), 1161–1168.
2. [2] Matsuo, T., Baba, Y., Hashiguchi, M., Takeshita, K., Dietary D-psicose, a C-3 epimer of D-fructose, suppresses the activity of hepatic lipogenic enzymes in rats. Asia Pacific J. Clin. Nutr. 10 (2001), 233–237.
3. [3] Sui, L., Dong, Y., Watanabe, Y., Yamaguchi, F., Hatano, N., Izumori, K., et al. Growth inhibitory effect of D-allose on human ovarian carcinoma cells in vitro. Anticancer Res. 25 (2005), 2639–2644.
4. [4] Ahmed, Z., Production of natural and rare pentoses using microorganisms and their enzymes. Electron. J. Biotechnol. 4 (2001), 103–111.
5. [5] Izumori, K., Izumoring A strategy for bioproduction of all hexoses. J. Biotechnol. 124 (2006), 717–722, 10.1016/j.jbiotec.2006.04.016.
6. [6] Takahashi, H., Iwai, Y., Hitomi, Y., Ikegami, S., Novel synthesis of L-ribose from D-mannono-1, 4-lactone. Org. Lett. 4 (2002), 2401–2403.
7. [7] Mark, L., Peterson, D.S.M., Synthesis of L-(+)-ribose via (s)-pinanediol (as)-a-bromo boronic esters. J. Org. Chem. 52 (1987), 5116–5121.
8. [8] Guo, J., Ye, X., Protecting groups in carbohydrate chemistry: influence on stereoselectivity of glycosylations. Molecules 15 (2010), 7235–7265, 10.3390/molecules15107235.
9. [9] Livesey, G., Brown, J.C., D-tagatose is a bulk sweetener with zero energy determined in rats. J. Nutr. 126 (1996), 1601–1609.
10. [10] Kim, P., Current studies on biological tagatose production using L-arabinose isomerase: a review and future perspective. Appl. Microbiol. Biotechnol. 65 (2004), 243–249, 10.1007/s00253-004-1665-8.
11. [11] Math, C., Gosselin, G., L-Nucleoside enantiomers as antivirals drugs: a mini-review. Antiviral Res. 71 (2006), 276–281, 10.1016/j.antiviral.2006.04.017.
12. [12] Chu, C.K., Ma, T., Shanmuganathan, K., Wang, C., Xiang, Y., Pai, S.B., et al. Use of 2 ’-fluoro-5-methyl- beta-l-arabinofuranosyluracil as a novel antiviral agent for hepatitis B virus and epstein-barr virus. Antimicrob. Agents Chemother. 39 (1995), 979–981.
13. [13] J.R. Beadle, J.P. Saunder, T.J. Wajada, Process for manufacturing tagatose. WO Patent 92/12263., 1992.
14. [14] Izumori, K., Miyoshi, T., Tokuda, S., Yamabe, K., Productoin of D-tagatose from dulcitol by Arthrobacter globiformis. Appl. Environ. Microbiol. 48 (1984), 1055–1057.
15. [15] Izumori, K., Tsuzaki, K., Production of D-tagatose from D-galactitol by Mycobacterium smegmatis. J. Ferment. Technol. 66 (1988), 225–227, 10.1016/0385-6380(88)90052-0.
16. [16] Muniruzzaman, S., Tokunaga, H., Izumori, K., Isolation of Enterobacter agglomerans strain 221e from soil, a potent D-tagatose producer from galactitol. J. Ferment. Bioeng. 78 (1994), 145–148, 10.1016/0922-338X(94)90253-4.
17. [17] Manzoni, M., Rollini, M., Bergomi, S., Biotransformation of D-galactitol to tagatose by acetic acid bacteria. Process Biochem. 36 (2001), 971–977.
18. [18] Zakaria, Ahmed, Tsuyoshi Shimonishi, S.H.B., Masaru, Utamura, Goro Takada, A.K.I., Biochemical preparation of L-ribose and- L-arabinose from ribitol: a new approach iiocii. J. Biosci. Bioeng. 88 (1999), 444–448.
19. [19] Beerens, K., Desmet, T., Soetaert, W., Enzymes for the biocatalytic production of rare sugars. J. Ind. Microbiol. Biotechnol. 39 (2012), 823–834, 10.1007/s10295-012-1089-x.
20. [20] Patel, D.H., Wi, S.G., Lee, S.G., Lee, D.S., Song, Y.H., Bae, H.J., Substrate specificity of the Bacillus licheniformis lyxose isomerase YdaE and its application in vitro catalysis for bioproduction of lyxose and glucose by two-step isomerization. Appl. Environ. Microbiol. 77 (2011), 3343–3350, 10.1128/AEM.02693-10.
21. [21] Yeom, S., Seo, E., Kim, B., Kim, Y., Oh, D., Characterization of a mannose-6-phosphate isomerase from thermus thermophilus and increased L-ribose production by its R142N mutant□. Appl. Environ. Microbiol. 77 (2011), 762–767, 10.1128/AEM.01793-10.
22. [22] Yeom, S.J., Ji, J.H., Kim, N.H., Park, C.S., Oh, D.K., Substrate specificity of a mannose-6-phosphate isomerase from bacillus subtilis and its application in the production of L-ribose. Appl. Environ. Microbiol. 75 (2009), 4705–4710, 10.1128/AEM.00310-09.
23. [23] Patel, M.J., Patel, A.T., Akhani, R., Dedania, S., Patel, D.H., Bioproduction of D-tagatose from D-galactose using phosphoglucose isomerase from Pseudomonas aeruginosa PAO1. Appl. Biochem. Biotechnol. 179 (2016), 715–727, 10.1007/s12010-016-2026-7.
24. [24] Cheetham, P.S.J., Wootton, A.N., Bioconversion of D-galactose into D-tagatose. Enzyme Microb. Technol. 15 (1993), 105–108, 10.1016/0141-0229(93)90032-W.
25. [25] Roh, H.J., Kim, P., Park, Y.C., Choi, J.H., Bioconversion of D-galactose into D-tagatose by expression of L-arabinose isomerase. Biotechnol. Appl. Biochem. 31:Pt 1 (2000), 1–4 10669396.
26. [26] Yeom, S., Ji, J., Kim, N., Park, C., Substrate specificity of a mannose-6-phosphate isomerase from Bacillus subtilis and its application in the production of L-ribose. Appl. Environ. Microbiol. 75 (2009), 4705–4710, 10.1128/AEM.00310-09.
27. [27] Yeom, S.J., Kim, N.H., Park, C.S., Oh, D.K., L-ribose production from L-arabinose by using purified L-arabinose isomerase and mannose-6-phosphate isomerase from Geobacillus thermodenitrificans. Appl. Environ. Microbiol. 75 (2009), 6941–6943, 10.1128/AEM.01867-09.
28. [28] Cho, E.A., Lee, D.W., Cha, Y.H., Lee, S.J., Jung, H.C., Pan, J.G., et al. Characterization of a novel D-lyxose isomerase from Cohnella laevoribosii RI-39 sp. nov. J. Bacteriol. 189 (2007), 1655–1663, 10.1128/JB.01568-06.
29. [29] Yoon, S.H., Kim, P., Oh, D.K., Properties of L-arabinose isomerase from Escherichia coli as biocatalyst for tagatose production. World J. Microbiol. Biotechnol. 19 (2003), 47–51, 10.1023/A.1022575601492.
30. [30] Lee, D.W., Choe, E.A., Kim, S.B., Eom, S.H., Hong, Y.H., Lee, S.J., et al. Distinct metal dependence for catalytic and structural functions in the L-arabinose isomerases from the mesophilic Bacillus halodurans and the thermophilic Geobacillus stearothermophilus. Arch. Biochem. Biophys. 434 (2005), 333–343, 10.1016/j.abb.2004.11.004.
31. [31] Zhang, H., Jiang, B., Pan, B., Purification and characterization of L-arabinose isomerase from Lactobacillus plantarum producing D-tagatose. World J. Microbiol. Biotechnol. 23 (2007), 641–646, 10.1007/s11274-006-9274-6.
32. [32] Xu, Z., Qing, Y., Li, S., Feng, X., Xu, H., Ouyang, P., A novel L-arabinose isomerase from Lactobacillus fermentum CGMCC2921 for D-tagatose production: gene cloning, purification and characterization. J. Mol. Catal. B Enzym. 70 (2011), 1–7, 10.1016/j.molcatb.2011.01.010.
33. [33] Kim, H.J., Oh, D.K., Purification and characterization of an L-arabinose isomerase from an isolated strain of Geobacillus thermodenitrificans producing D-tagatose. J. Biotechnol. 120 (2005), 162–173, 10.1016/j.jbiotec.2005.06.004.
34. [34] Kim, J.W., Kim, Y.W., Roh, H.J., Kim, H.Y., Cha, J.H., Park, K.H., et al. Production of tagatose by a recombinant thermostable L-arabinose isomerase from Thermus sp. IM6501. Biotechnol. Lett. 25 (2003), 963–967, 10.1023/A.1024069813839.
35. [35] Jørgensen, F., Hansen, O.C., Stougaard, P., Enzymatic conversion of D-galactose to D-tagatose: heterologous expression and characterisation of a thermostable L-arabinose isomerase from Thermoanaerobacter mathranii. Appl. Microbiol. Biotechnol. 64 (2004), 816–822, 10.1007/s00253-004-1578-6.
36. [36] Lee, D., Jang, H., Choe, E., Kim, B., Lee, S., Kim, S., et al. Characterization of a thermostable L-arabinose (D-galactose) isomerase from the hyperthermophilic eubacterium thermotoga maritima. Appl. Environ. Microbiol. 70 (2004), 1397–1404, 10.1128/AEM.70.3.1397.
37. [37] Kim, B.C., Lee, Y.H., Lee, H.S., Lee, D.W., Choe, E.A., Pyun, Y.R., Cloning, expression and characterization of L-arabinose isomerase from Thermotoga neapolitana: bioconversion of D-galactose to D-tagatose using the enzyme. FEMS Microbiol. Lett. 212 (2002), 121–126, 10.1016/S0378-1097(02)00715-2.
38. [38] Sambrook, J.R.D., Molecular Cloning: a Laboratory Manual. 3rd ed., 2001, Cold Spring Harbor Laboratory Press, NY.
39. [39] Kulka, R.G., Colorimetric estimation of ketopentoses and ketohexoses. Biochem. J. 63 (1956), 542–548.
40. [40] Bradford, M., A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976), 248–254.
41. [41] Lee, S.J., Lee, D.W., Choe, E.A., Hong, Y.H., Kim, S.B., Kim, B.C., et al. Characterization of a thermoacidophilic L-arabinose isomerase from Alicyclobacillus acidocaldarius: role of Lys-269 in pH optimum. Appl. Environ. Microbiol. 71 (2005), 7888–7896, 10.1128/AEM.71.12.7888-7896.2005.
42. [42] Oh, D.K., Tagatose Properties, applications, and biotechnological processes. Appl. Microbiol. Biotechnol. 76 (2007), 1–8, 10.1007/s00253-007-0981-1.
43. [43] Patrick, J.W., Lee, N., Purification and properties of an coli purification Escherichia and properties coli * of an L-arabinose isomerase from. J. Biol. Chem. 261 (1968), 4312–4318.
44. [44] Chouayekh, H., Bejar, W., Rhimi, M., Jelleli, K., Mseddi, M., Bejar, S., Characterization of an L-arabinose isomerase from the Lactobacillus plantarum NC8 strain showing pronounced stability at acidic pH. FEMS Microbiol. Lett. 277 (2007), 260–267, 10.1111/j.1574-6968.2007.00961.x.
45. [45] H. Kim, S. Ryu, P. Kim, D. Oh, A Feasible Enzymatic Process for D-Tagatose Production by an Immobilized Thermostable L-Arabinose Isomerase in a Packed-Bed Bioreactor 2003:400–4. 10.1021/bp025675f.
46. [46] Oh, H.J., Kim, H.J., Oh, D.K., Increase in D-tagatose production rate by site-directed mutagenesis of L-arabinose isomerase from Geobacillus thermodenitrificans. Biotechnol. Lett. 28 (2006), 145–149, 10.1007/s10529-005-5327-4.
47. [47] Helanto, M., Kiviharju, K., Granström, T., Leisola, M., Nyyssölä, A., Biotechnological production of L-ribose from L-arabinose. Appl. Microbiol. Biotechnol. 83 (2009), 77–83, 10.1007/s00253-008-1855-x.
48. [48] Kim, K.R., Seo, E.S., Oh, D.K., L-ribose production from L-arabinose by immobilized recombinant Escherichia coli co-expressing the L-arabinose isomerase and mannose-6-phosphate isomerase genes from Geobacillus thermodenitrificans. Appl. Biochem. Biotechnol. 172 (2014), 275–288, 10.1007/s12010-013-0547-x.
49. [49] Lim, Y., Yeom, S., Oh, D., Production of L-ribose from L-ribulose by a triple-site variant of mannose-6-phosphate isomerase from Geobacillus thermodenitrificans. Appl. Environ. Microbiol. 78 (2012), 3880–3884, 10.1128/AEM.07012-11.
50. [50] Woodyer, R.D., Wymer, N.J., Racine, F.M., Khan, S.N., Saha, B.C., Efficient production of L-ribose with a recombinant Escherichia coli biocatalyst efficient production of L-ribose with a recombinant Escherichia coli biocatalyst□. Appl. Environ. Microbiol. 74 (2008), 2967–2975, 10.1128/AEM.02768-07.
51. [51] Akagi, M., Omae, D., Tamura, Y., Ueda, T., Kumashiro, T., Urata, H., A practical synthesis of L-ribose. Chem. Pharm. Bull. (Tokyo) 50 (2002), 866–868, 10.1248/cpb.50.866.