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Metabolic engineering pathways for rare sugars biosynthesis, physiological functionalities, and applications—a review

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References

  • Ahmed, Z. (2001). Production of natural and rare pentoses using microorganisms and their enzymes. Electron. J.Biotechnol. 4(2):13–14.
  • Ajikumar, P. K., Xiao, W. H., Tyo, K. E., Wang, Y., Simeon, F., Leonard, E., … and Stephanopoulos, G. (2010). Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli. Science. 330(6000):70–74.
  • Bär, A. and Leeman, W. R. (1999). l-Sorbose but notd-tagatose induces hemolysis of dog erythrocytes in vitro. Regul. Toxicol.Pharmacol. 29(2):S43–S45.
  • Bautista, D. A., Pegg, R. B. and Shand, P. J. (2000). Effect of L-glucose and D-tagatose on bacterial growth in media and a cooked cured ham product. J. Food Prot. 63(1):71–77.
  • Beerens, K., Desmet, T. and Soetaert, W. (2012). Enzymes for the biocatalytic production of rare sugars. J.Ind. Microbiol.Biotechnol. 39(6):823–834.
  • Börgel, D., van den Berg, M., Hüller, T., Andrea, H., Liebisch, G., Boles, E., … and van der Hoeven, R. (2012). Metabolic engineering of the non-conventional yeast Pichia ciferrii for production of rare sphingoid bases. Metab. Eng. 14(4):412–426.
  • Brovetto, M., Gamenara, D., Saenz Mendez, P. and Seoane, G. A. (2011). C− C bond-forming lyases in organic synthesis. Chem. Rev. 111(7):4346–4403.
  • Cai, L. (2011). A Chemoenzymatic Route to Unnatural Sugar Nucleotides and Their Applications and Enzymatic Synthesis of Rare Sugars with Aldolases In vitro and In vivo (Doctoral dissertation, The Ohio State University).
  • Chung, Y. M., Hyun Lee, J., Youl Kim, D., Hwang, S. H., Hong, Y. H., Kim, S. B., … and Hye Park, C. (2012). Dietary d‐psicose reduced visceral fat mass in high‐fat diet‐induced obese rats. J.Food Sci. 77(2):H53–H58.
  • Clapés, P., Fessner, W. D., Sprenger, G. A. and Samland, A. K. (2010). Recent progress in stereoselective synthesis with aldolases. Curr. Opin.Chem. Biol. 14(2):154–167.
  • Da Silva, G. P., Mack, M. and Contiero, J. (2009). Glycerol: a promising and abundant carbon source for industrial microbiology. Biotechnol. Adv. 27(1):30–39.
  • D’Alonzo, D., Guaragna, A. and Palumbo, G. (2009). Recent advances in monosaccharide synthesis: a journey into L-hexose world. Curr. Org. Chem. 13(1):71–98.
  • Emmadi, M. and Kulkarni, S. S. (2014). Recent advances in synthesis of bacterial rare sugar building blocks and their applications. Nat. Prod. Rep. 31(7):870–879.
  • Espinosa, I. and Fogelfeld, L. (2010). Tagatose: from a sweetener to a new diabetic medication?. Expert Opin.Invest. Drugs 19(2):285–294.
  • Franke, D., Machajewski, T., Hsu, C. C. and Wong, C. H. (2003). One-pot synthesis of L-fructose using coupled multienzyme systems based on rhamnulose-1-phosphate aldolase. J.Org. Chem. 68(17):6828–6831.
  • Fukada, K., Ishii, T., Tanaka, K., Yamaji, M., Yamaoka, Y., Kobashi, K. I. and Izumori, K. (2010). Crystal structure, solubility, and mutarotation of the rare monosaccharide D-psicose. Bull.Chem. Soc. Jpn. 83(10):1193–1197.
  • Gao, D., Kawai, N. and Tamiya, T. (2011). The anti-inflammatory effects of D-allose contribute to attenuation of cerebral ischemia–reperfusion injury. Med. Hypotheses. 76(6):911–913.
  • Granström, T. B., Izumori, K. and Leisola, M. (2007). A rare sugar xylitol. Part II: biotechnological production and future applications of xylitol. Appl. Microbiol.Biotechnol. 74(2):273.
  • Gullapalli, P., Shiji, T., Rao, D., Yoshihara, A., Morimoto, K., Takata, G., … and Izumori, K. (2007). Bioproduction of a novel sugar 1-deoxy-L-fructose by Enterobacter aerogenes IK7; isomerization of a 6-deoxyhexose to a 1-deoxyhexose. Tetrahedron: Asymmetry 18(16):1995–2000.
  • Guo, Z. and Wang, Q. (2009). Recent development in carbohydrate-based cancer vaccines. Curr. Opin.Chem. Biol. 13(5):608–617.
  • Harada, M., Kondo, E., Hayashi, H., Suezawa, C., Suguri, S. and Arai, M. (2012). d-Allose and d-psicose reinforce the action of metronidazole on trichomonad. Parasitol. Res. 110(4):1565–1567.
  • Hayashi, N., Iida, T., Yamada, T., Okuma, K., Takehara, I., Yamamoto, T., … and Tokuda, M. (2010). Study on the postprandial blood glucose suppression effect of D-psicose in borderline diabetes and the safety of long-term ingestion by normal human subjects. Biosci., Biotechnol.Biochem. 74(3):510–519.
  • Hirata, Y., Saito, M., Tsukamoto, I., Yamaguchi, F., Sui, L., Kamitori, K., … and Tokuda, M. (2009). Analysis of the inhibitory mechanism of D-allose on MOLT-4F leukemia cell proliferation. J.Biosci.Bioeng. 107(5):562–568.
  • Hossain, M. A., Izuishi, K. and Maeta, H. (2003). Protective effects of d‐allose against ischemia reperfusion injury of the rat liver. J.Hepato-biliary-Pancreat. Surg. 10(3):218–225.
  • Hossain, M. A., Izuishi, K., Tokuda, M., Izumori, K. and Maeta, H. (2004). d‐Allose has a strong suppressive effect against ischemia/reperfusion injury: a comparative study with allopurinol and superoxide dismutase. J.Hepato-Biliary-Pancreat. Surg. 11(3):181–189.
  • Hossain, M. A., Kitagaki, S., Nakano, D., Nishiyama, A., Funamoto, Y., Matsunaga, T., … and Hirata, Y. (2011). Rare sugar D-psicose improves insulin sensitivity and glucose tolerance in type 2 diabetes Otsuka Long-Evans Tokushima Fatty (OLETF) rats. Biochem.Biophys. Res. Commun. 405(1):7–12.
  • Iga, Y., Nakamichi, K., Shirai, Y. and Matsuo, T. (2010). Acute and sub-chronic toxicity of D-allose in rats. Biosci., Biotechnol.,Biochem. 74(7):1476–1478.
  • Itoh, H. and Izumori, K. (1996). Enzymatic production of L-tagatose and L-fructose from L-sorbose and L-psicose, respectively. J.Ferment.Bioeng. 81(4):351–353.
  • Izumori, K. (2006). Izumoring: a strategy for bioproduction of all hexoses. J.Biotechnol. 124(4):717–722.
  • Jayamuthunagai, J., Gautam, P., Srisowmeya, G. and Chakravarthy, M. (2016). Biocatalytic production of D-tagatose: A potential rare sugar with versatile applications. Crit. Rev. Food. Sci. Nutr. doi, 10(10408398.2015), 1126550.
  • Jung, W. S., Kang, J. H., Chu, H. S., Choi, I. S. and Cho, K. M. (2014). Elevated production of 3-hydroxypropionic acid by metabolic engineering of the glycerol metabolism in Escherichia coli. Metab. Eng. 23:116–122.
  • Kano, A., Gomi, K., Yamasaki-Kokudo, Y., Satoh, M., Fukumoto, T., Ohtani, K., … and Tada, Y. (2010). A rare sugar, D-allose, confers resistance to rice bacterial blight with upregulation of defense-related genes in Oryza sativa. Phytopathology 100(1):85–90.
  • Kawakami, K., Hasegawa, Y., Zhang, S., Yoshihashi, Y., Yonemochi, E. and Terada, K. (2014). Low‐density microparticles with petaloid surface structure for pulmonary drug delivery. J.Pharm. Sci. 103(4):1309–1313.
  • Kim, P. (2004). Current studies on biological tagatose production using L-arabinose isomerase: a review and future perspective. Appl. Microbiol. Biotechnol. 65(3):243–249.
  • Krämer, L. and Steckhan, E. (1997). Colmmobilization of L-α-glycerophosphate oxidase with catalase and its application for the synthesis of dihydroxyacetone phosphate. Tetrahedron 53(43):14645–14650.
  • Lerner, L. M. and Mennitt, G. (1994). A new synthesis ofL-talose and preparation of its adenine nucleosides. Carbohydr. Res. 259(2):191–200.
  • Levin, G.V. (2002). Tagatose, the new GRAS sweetener and health product. J. med. food. 5:23–26.
  • Li, B., Varanasi, S. and Relue, P. (2013). High yield aldose–ketose transformation for isolation and facile conversion of biomass sugar to furan. Green Chem. 15(8):2149–2157.
  • Li, Z., Cai, L., Qi, Q. and Wang, P. G. (2011). Enzymatic synthesis of D-sorbose and D-psicose with aldolase RhaD: effect of acceptor configuration on enzyme stereoselectivity. Bioorg.Med. Chem. Lett. 21(23):7081–7084.
  • Lim, Y. R. and Oh, D. K. (2011). Microbial metabolism and biotechnological production of d-allose. Appl. Microbiol.Biotechnol. 91(2):229–235.
  • Livesey, G. and Brown, J. C. (1995). Whole body metabolism is not restricted to D-sugars because energy metabolism of L-sugars fits a computational model in rats. J.Nutr. 125(12):3020.
  • Machajewski, T. D. and Wong, C. H. (2000). The catalytic asymmetric aldol reaction. Angew. Chemie Int. Ed. 39(8):1352–1375.
  • Mäki-Arvela, P., Salmi, T., Holmbom, B., Willfoör, S. and Murzin, D. Y. (2011). Synthesis of sugars by hydrolysis of hemicelluloses-a review. Chem. Rev. 111(9):5638–5666.
  • Mathé, C. and Gosselin, G. (2006). L-nucleoside enantiomers as antivirals drugs: a mini-review. Antivir. Res. 71(2):276–281.
  • Matsuo, T. and Izumori, K. (2009). Retraction: D-psicose inhibits intestinal α-glucosidase and suppresses the glycemic response after ingestion of carbohydrates in rats. J.Clin. Biochem.Nutr. 45(2):202–206.
  • Matsuo, T., Suzuki, H., Hashiguchi, M. and Izumori, K. (2002). D-Psicose is a rare sugar that provides no energy to growing rats. J.Nutr. Sci.Vitaminol. 48(1):77–80.
  • McCarthy, E. T., Sharma, M. and Savin, V. J. (2010). Circulating permeability factors in idiopathic nephrotic syndrome and focal segmental glomerulosclerosis. Clin. J.Am. Soc. Nephrol. 5(11):2115–2121.
  • Men, Y., Zhu, Y., Zhang, L., Kang, Z., Izumori, K., Sun, Y. and Ma, Y. (2014). Enzymatic conversion of D-galactose to D-tagatose: cloning, overexpression and characterization of L-arabinose isomerase from Pediococcus pentosaceus PC-5. Microbiol. Res. 169(2):171–178.
  • Mitani, T., Hoshikawa, H., Mori, T., Hosokawa, T., Tsukamoto, I., Yamaguchi, F., … and Mori, N. (2009). Growth inhibition of head and neck carcinomas by D‐allose. Head Neck 31(8):1049–1055.
  • Moghaddam, M. R. B. and Van den Ende, W. (2012). Sugars and plant innate immunity. J Exp Bot 63(11):3989–3998.
  • Mu, W., Zhang, W., Feng, Y., Jiang, B. and Zhou, L. (2012). Recent advances on applications and biotechnological production of D-psicose. Appl. Microbiol.Biotechnol. 94(6):1461–1467.
  • Muniruzzaman, S., Pan, Y. T., Zeng, Y., Atkins, B., Izumori, K. and Elbein, A. D. (1996). Inhibition of glycoprotein processing by L-fructose and L-xylulose. Glycobiology 6(8):795–803.
  • Murata, A., Sekiya, K., Watanabe, Y., Yamaguchi, F., Hatano, N., Izumori, K. and Tokuda, M. (2003). A novel inhibitory effect of D-allose on production of reactive oxygen species from neutrophils. J.Biosci.Bioeng. 96(1):89–91.
  • Naha, N., Lee, H. Y., Jo, M. J., Chung, B. C., Kim, S. H. and Kim, M. O. (2008). Rare sugar D-allose induces programmed cell death in hormone refractory prostate cancer cells. Apoptosis 13(9):1121–1134.
  • Nakamura, T., Tanaka, S., Hirooka, K., Toyoshima, T., Kawai, N., Tamiya, T., … and Miyamoto, O. (2011). Anti-oxidative effects of d-allose, a rare sugar, on ischemia-reperfusion damage following focal cerebral ischemia in rat. Neurosci. Lett. 487(1):103–106.
  • O’charoen, S., Hayakawa, S. and Ogawa, M. (2015). Food properties of egg white protein modified by rare ketohexoses through Maillard reaction. Int. J. Food Sci. Technol. 50(1):194–202.
  • Ochiai, M., Onishi, K., Yamada, T., Iida, T. and Matsuo, T. (2014). D-Psicose increases energy expenditure and decreases body fat accumulation in rats fed a high-sucrose diet. Int. J.Food Sci.Nutr. 65(2):245–250.
  • Oshima, H., Kimura, I. and Izumori, K. (2006). Psicose contents in various food products and its origin. Food Sci.Technol. Res. 12(2):137–143.
  • Pagliaro, M., Ciriminna, R., Kimura, H., Rossi, M. and Della Pina, C. (2007). From glycerol to value‐added products. Angew. Chemie Int. Ed. 46(24):4434–4440.
  • Perali, R. S., Mandava, S. and Bandi, R. (2011). A convenient synthesis of L-ribose from D-fructose. Tetrahedron 67(22):4031–4035.
  • Quaglia, D., Irwin, J. A. and Paradisi, F. (2012). Horse liver alcohol dehydrogenase: new perspectives for an old enzyme. Mol. Biotechnol. 52(3):244–250.
  • Rao, D., Gullapalli, P., Yoshihara, A., Jenkinson, S. F., Morimoto, K., Takata, G., … and Izumori, K. (2008). Direct production of L-tagatose from L-psicose by Enterobacter aerogenes 230S. J.Biosci.Bioeng. 106(5):473–480.
  • Romano, A. H. and Conway, T. (1996). Evolution of carbohydrate metabolic pathways. Res. Microbiol. 147(6–7):448–455.
  • Samland, A. K. and Sprenger, G. A. (2006). Microbial aldolases as C–C bonding enzymes—unknown treasures and new developments. Appl. Microbiol. Biotechnol. 71(3):253.
  • Schümperli, M., Pellaux, R. and Panke, S. (2007). Chemical and enzymatic routes to dihydroxyacetone phosphate. Appl. Microbiol.Biotechnol. 75(1):33.
  • Segerman, Z. J., Roy, B. and Hecht, S. M. (2013). Characterization of bleomycin-mediated cleavage of a hairpin DNA library. Biochem. 52(31):5315–5327.
  • Shuang-Yan, T. (2012). Rare sugars: Applications and enzymatic production. J. Biocatal. Biotransform. 1:2. https://doi.org/10.4172/2324-9099.1000e105.
  • Sui, L., Nomura, R., Dong, Y., Yamaguchi, F., Izumori, K. and Tokuda, M. (2007). Cryoprotective effects of D-allose on mammalian cells. Cryobiology 55(2):87–92.
  • Sun, Y., Hayakawa, S., Puangmanee, S. and Izumori, K. (2006). Chemical properties and antioxidative activity of glycated α-lactalbumin with a rare sugar, D-allose, by Maillard reaction. Food Chem. 95(3):509–517.
  • Tetsuo, I. I. D. A., Kishimoto, Y., Yoshikawa, Y., Hayashi, N., Okuma, K., Mikiko, T. O. H. I., … and IZUMORI, K. (2008). Acute D-psicose administration decreases the glycemic responses to an oral maltodextrin tolerance test in normal adults. J.Nutr. Sci.Vitaminol. 54(6):511–514.
  • Trinh, C. T. and Srienc, F. (2009). Metabolic engineering of Escherichia coli for efficient conversion of glycerol to ethanol. Appl.Environ. Microbiol. 75(21):6696–6705.
  • Truniger, V. and Boos, W. (1994). Mapping and cloning of gldA, the structural gene of the Escherichia coli glycerol dehydrogenase. J.Bacteriol. 176(6):1796–1800.
  • Ueki, M., Asaga, T., Chujo, K., Ono, J., Iwanaga, Y. and Taie, S. (2008). D-allose protects against endotoxemic acute renal injury. J.Biosci.Bioeng. 105(5):481–485.
  • Viswanath-Reddy, M., PYLE, J. E. and HOWE, H. B. JR (1978). Purification and properties of NADP+-linked glycerol dehydrogenase from Neurospora crassa. Microbiology 107(2):289–296.
  • Wei, M., Li, Z., Li, T., Wu, B., Liu, Y., Qu, J., … and Wang, P. G. (2015). Transforming flask reaction into cell-based synthesis: production of polyhydroxylated molecules via engineered escherichia coli. Acs Catal. 5(7):4060–4065.
  • Wen, L., Zheng, Y., Li, T. and Wang, P. G. (2016). Enzymatic synthesis of 3-deoxy-d-manno-octulosonic acid (KDO) and its application for LPS assembly. Bioorg.Med. Chem. Lett. 26(12):2825–2828.
  • Wheeler, G. L., Jones, M. A. and Smirnoff, N. (1998). The biosynthetic pathway of vitamin C in higher plants. Nature 393(6683):365–369.
  • Xia, T. Y., Li, Y. B., Yin, Z. J., Meng, X. B., Li, S. C. and Li, Z. J. (2014). Synthesis of L-glucose and L-galactose derivatives from D-sugars. Chin. Chem. Lett. 25(9):1220–1224.
  • Yamada, K., Noguchi, C., Kamitori, K., Dong, Y., Hirata, Y., Hossain, M. A., … and Yamaguchi, F. (2012). Rare sugar D-allose strongly induces thioredoxin-interacting protein and inhibits osteoclast differentiation in Raw264 cells. Nutr. Res. 32(2):116–123.
  • Yamaguchi, F., Kamitori, K., Sanada, K., Horii, M., Dong, Y., Sui, L. and Tokuda, M. (2008). Rare sugar D-allose enhances anti-tumor effect of 5-fluorouracil on the human hepatocellular carcinoma cell line HuH-7. J.Biosci.Bioeng. 106(3):248–252.
  • Yang, J., Zhu, Y., Li, J., Men, Y., Sun, Y. and Ma, Y. (2015). Biosynthesis of rare ketoses through constructing a recombination pathway in an engineered Corynebacterium glutamicum. Biotechnol.Bioeng. 112(1):168–180.
  • Yang, J., Zhu, Y., Men, Y., Sun, S., Zeng, Y., Zhang, Y., … and Ma, Y. (2016). Pathway construction in Corynebacterium glutamicum and strain engineering to produce rare sugars from glycerol. J. Agric. Food Chem. 64(50):9497–9505.
  • Yin, Z. and Huang, X. (2012). Recent development in carbohydrate based anticancer vaccines. J.Carbohydr. Chem. 31(3):143–186.
  • Yu, Z., Schmaltz, R. M., Bozeman, T. C., Paul, R., Rishel, M. J., Tsosie, K. S. and Hecht, S. M. (2013). Selective tumor cell targeting by the disaccharide moiety of bleomycin. J.Am. Chem. Soc. 135(8):2883–2886.
  • Zhang, W., Yu, S., Zhang, T., Jiang, B. and Mu, W. (2016). Recent advances in D-allulose: Physiological functionalities, applications, and biological production. Trends Food Sci. Technol. 54:127–137.
  • Zulueta, M. M. L., Zhong, Y. Q. and Hung, S. C. (2013). Synthesis of L-hexoses and their related biomolecules. Chem. Commun. 49(32):3275–3287.

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