Synthesis of rebaudioside D, using glycosyltransferase UGTSL2 and in situ UDP-glucose regeneration

Food Chemistry

Volumn 259, Issue , 2018, Pages 286-291

  Chen, Liangliang ^a   Sun, Ping ^a   Zhou, Fangfang ^a   Li, Yan ^a,b   Chen, Kequan ^a   Jia, Honghua ^a   Yan, Ming ^a   Gong, Dachun ^b   Ouyang, Pingkai ^a  

^a NANJING TECH UNIVERSITY   (China)

^b CHINA THREE GORGES UNIVERSITY   (China)

Author keywords

Rebaudioside D; Rebaudioside M2; Stevia rebaudiana; UDP glycosyltransferase; UGTSL2

Indexed keywords

SUGAR (SUCROSE); SUGAR SUBSTITUTES;

GLUCOSYLTRANSFERASES; GLYCOSYL TRANSFERASE; REACTION PARAMETERS; REBAUDIOSIDE M2; SOLANUM LYCOPERSICUM; STEVIA REBAUDIANA; SUCROSE CONCENTRATION; UGTSL2;

GLUCOSE;

GLUCOSYLTRANSFERASE; GLYCOSYLTRANSFERASE; POLYHISTIDINE TAG; REBAUDIOSIDE A; REBAUDIOSIDE D; RECOMBINANT PROTEIN; STEVIOSIDE; SUCROSE; SUCROSE SYNTHASE; SWEETENING AGENT; UDP GLUCOSYLTRANSFERASE; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE; URIDINE DIPHOSPHATE GLUCOSE; GLYCOSIDE; KAURANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PARAMETERS; CLINICAL EVALUATION; CONCENTRATION PROCESS; DRY WEIGHT; GLYCOSYLATION; NONHUMAN; PLANT LEAF; POTATO; PROTEIN EXPRESSION; REACTION ANALYSIS; REACTION TIME; STEVIA REBAUDIANA; SWEETNESS; SYNTHESIS; TEMPERATURE; TOMATO; BIOSYNTHESIS; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ENZYMOLOGY; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; METABOLISM; SOLANUM; STEVIA;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DITERPENES, KAURANE; GLUCOSYLTRANSFERASES; GLYCOSIDES; GLYCOSYLTRANSFERASES; PLANT LEAVES; RECOMBINANT PROTEINS; SOLANUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEVIA; TEMPERATURE; URIDINE DIPHOSPHATE GLUCOSE;

EID: 85044757730     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2018.03.126     Document Type: Article

References (28)

1. Allen, A.L., Mcgeary, J.E., Hayes, J.E., Rebaudioside A and rebaudioside D bitterness do not covary with Acesulfame-K bitterness or polymorphisms in TAS2R9 and TAS2R31. Chemosensory Perception 6:3 (2013), 109–117.
2. Bradford, M.M., A rapid and sensitive method for the quantitation of microgram quantities utilizing the principle of protein-dye binding. Analytical Biochemistry 72:s 1–2 (1976), 248–254.
3. Brandle, J.E., Starratt, A.N., Gijzen, M., Stevia rebaudiana: Its agricultural, biological, and chemical properties. Canadian Journal of Plant Science 78:4 (1998), 527–536.
4. Chaturvedula, V.S.P., Prakash, I., A new diterpene glycoside from Stevia rebaudiana. Molecules 16:4 (2011), 2937–2943.
5. Chaturvedula, V.S.P., Prakash, I., Structures of the novel diterpene glycosides from Stevia rebaudiana. Carbohydrate Research 346:8 (2011), 1057–1060.
6. Chaturvedula, V.S.P., Rhea, J., Milanowski, D., Mocek, U., Prakash, I., Two minor diterpene glycosides from the leaves of Stevia rebaudiana. Natural Product Communications 6:2 (2011), 175–178.
7. Chaturvedula, V.S.P., Upreti, M., Prakash, I., Structures of the novel α-glucosyl linked diterpene glycosides from Stevia rebaudiana. Carbohydrate Research 346:13 (2011), 2034–2038.
8. De Bruyn, F., Maertens, J., Beauprez, J., Soetaert, W., De Mey, M., Biotechnological advances in UDP-sugar based glycosylation of small molecules. Biotechnology Advances 33:2 (2015), 288–302.
9. Georgiou, G., Valax, P., Isolating inclusion bodies from bacteria. Methods in Enzymology 309 (1999), 48–58.
10. Křen, V., Thiem, J., Glycosylation employing bio-systems: From enzymes to whole cells. Chemical Society Reviews 26:6 (1997), 463–473.
11. Lim, E.K., Plant glycosyltransferases: Their potential as novel biocatalysts. Chemistry-A European Journal 11:19 (2005), 5486–5494.
12. Lineweaver, H., Burk, D., The determination of enzyme dissociation constants. Journal of the American Chemical Society 56:3 (1934), 658–666.
13. Madhav, H., Bhasker, S., Chinnamma, M., Functional and structural variation of uridine diphosphate glycosyltransferase (UGT) gene of Stevia rebaudiana-UGTSr involved in the synthesis of rebaudioside A. Plant Physiology and Biochemistry 63:4 (2013), 245–253.
14. Miller, G.L., Use of dinitrosalicylic acid reagent for determination of reducing sugar. Analytical Biochemistry 31:3 (1959), 426–428.
15. Nikiforov, A.I., Rihner, M.O., Eapen, A.K., Thomas, J.A., Metabolism and toxicity studies supporting the safety of rebaudioside D. International Journal of Toxicology 32:4 (2013), 261–273.
16. Ohta, M., Sasa, S., Inoue, A., Tamai, T., Fujita, I., Morita, K., Matsuura, F., Characterization of novel steviol glycosides from leaves of Stevia rebaudiana Morita. Journal of Applied Glycoseience 57:3 (2010), 199–209.
17. Olsson, K., Carlsen, S., Semmler, A., Simon, E., Mikkelsen, M.D., Moller, B.L., Microbial production of next-generation stevia sweeteners. Microbial Cell Factories 15:1 (2016), 207–220.
18. Philippe, R.N., De Mey, M., Anderson, J., Ajikumar, P.K., Biotechnological production of natural zero-calorie sweeteners. Current Opinion in Biotechnology 26 (2014), 155–161.
19. Prakash, I., Bunders, C., Devkota, K.P., Charan, R.D., Ramirez, C., Parikh, M., Markosyan, A., Isolation and structure elucidation of rebaudioside D2 from bioconversion reaction of rebaudioside A to rebaudioside D. Natural Product Communications 9:8 (2014), 1135–1138.
20. Prakash, I., Bunders, C., Devkota, K.P., Charan, R.D., Ramirez, C., Priedemann, C., Markosyan, A., Isolation and characterization of a novel rebaudioside M isomer from a bioconversion reaction of rebaudioside A and NMR comparison studies of rebaudioside M isolated from Stevia rebaudiana Bertoni and Stevia rebaudiana Morita. Biomolecules 4:2 (2014), 374–389.
21. Prakash, I., Bunders, C., Devkota, K.P., Charan, R.D., Ramirez, C., Snyder, T.M., Ter Halle, R., Bioconversion of rebaudioside I from rebaudioside A. Molecules 19:11 (2014), 17345–17355.
22. Purkayastha, S., Markosyan, A., Prakash, I., Bhusari, S., Pugh, G. Jr., Lynch, B., Roberts, A., Steviol glycosides in purified stevia leaf extract sharing the same metabolic fate. Regulatory Toxicology and Pharmacology 77 (2016), 125–133.
23. Richman, A., Swanson, A., Humphrey, T., Chapman, R., McGarvey, B., Pocs, R., Brandle, J., Functional genomics uncovers three glucosyltransferases involved in the synthesis of the major sweet glucosides of Stevia rebaudiana. The Plant Journal 41:1 (2005), 56–67.
24. Sauerzapfe, B., Engels, L., Elling, L., Broadening the biocatalytic properties of recombinant sucrose synthase 1 from potato (Solanum tuberosum L.) by expression in Escherichia coli and Saccharomyces cerevisiae. Enzyme and Microbial Technology 43:3 (2008), 289–296.
25. Schmolzer, K., Gutmann, A., Diricks, M., Desmet, T., Nidetzky, B., Sucrose synthase: A unique glycosyltransferase for biocatalytic glycosylation process development. Biotechnology Advances 34:2 (2016), 88–111.
26. Wang, J., Li, S., Xiong, Z., Wang, Y., Pathway mining-based integration of critical enzyme parts for de novo biosynthesis of steviolglycosides sweetener in Escherichia coli. Cell Research 26:2 (2016), 258–261.
27. Wang, Y., Chen, L.L., Li, Y., Li, Y.Y., Yan, M., Chen, K.Q., Xu, L., Efficient enzymatic production of rebaudioside A from stevioside. Bioscience, Biotechnology, and Biochemistry 80:1 (2015), 67–73.
28. Wolwer-Rieck, U., The leaves of Stevia rebaudiana (Bertoni), their constituents and the analyses thereof: A review. Journal of Agricultural and Food Chemistry 60:4 (2012), 886–895.