메뉴 건너뛰기




Volumn 101, Issue , 2015, Pages 191-199

Biosynthesis of amino deoxy-sugar-conjugated flavonol glycosides by engineered Escherichia coli

Author keywords

Biocatalysis; Biosynthesis; Biotransformations; Fermentation; Glycosylation; Unnatural flavonoids

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; CARBON; ESCHERICHIA COLI; FERMENTATION; GENES; GLUCOSE; GLYCOSYLATION; PHENOLS; PLANTS (BOTANY); SUGARS;

EID: 84931270407     PISSN: 1369703X     EISSN: 1873295X     Source Type: Journal    
DOI: 10.1016/j.bej.2015.05.017     Document Type: Article
Times cited : (17)

References (45)
  • 1
    • 49749126041 scopus 로고    scopus 로고
    • Sweet antibiotics - the role of glycosidic residues in antibiotic and antitumor activity and their randomization
    • Kren V., Rezanka T. Sweet antibiotics - the role of glycosidic residues in antibiotic and antitumor activity and their randomization. FEMS Microbiol. Rev. 2008, 32:858-889.
    • (2008) FEMS Microbiol. Rev. , vol.32 , pp. 858-889
    • Kren, V.1    Rezanka, T.2
  • 2
    • 0031127564 scopus 로고    scopus 로고
    • The role of carbohydrates in biologically active natural products
    • Weymouth-Wilson A.C. The role of carbohydrates in biologically active natural products. Nat. Prod. Rep. 1997, 14:99-110.
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 99-110
    • Weymouth-Wilson, A.C.1
  • 4
    • 84922649036 scopus 로고    scopus 로고
    • Advances in the biotechnological glycosylation of valuable flavonoids
    • Xiao J., Muzashvili T.S., Georgiev M.I. Advances in the biotechnological glycosylation of valuable flavonoids. Biotechnol. Adv. 2014, 32:1145-1156.
    • (2014) Biotechnol. Adv. , vol.32 , pp. 1145-1156
    • Xiao, J.1    Muzashvili, T.S.2    Georgiev, M.I.3
  • 5
    • 84923100134 scopus 로고    scopus 로고
    • Harnessing sugar biosynthesis and glycosylation to redesign natural products and to increase structural diversity
    • John Wiley & Sons, Inc., New Jersey, A. Osbourn, R.J. Goss, G.T. Carter (Eds.)
    • Olano C., Mendez C., Salas J.A. Harnessing sugar biosynthesis and glycosylation to redesign natural products and to increase structural diversity. Natural Products: Discourse, Diversity, and Design 2014, 317-339. John Wiley & Sons, Inc., New Jersey. A. Osbourn, R.J. Goss, G.T. Carter (Eds.).
    • (2014) Natural Products: Discourse, Diversity, and Design , pp. 317-339
    • Olano, C.1    Mendez, C.2    Salas, J.A.3
  • 6
    • 84902263494 scopus 로고    scopus 로고
    • Recent advances in synthesis of bacterial rare sugar building blocks and their applications
    • Emmadi M., Kulkarni S.S. Recent advances in synthesis of bacterial rare sugar building blocks and their applications. Nat. Prod. Rep. 2014, 31:870-879.
    • (2014) Nat. Prod. Rep. , vol.31 , pp. 870-879
    • Emmadi, M.1    Kulkarni, S.S.2
  • 7
    • 84887957079 scopus 로고    scopus 로고
    • Recent developments on synthetic tools towards structural and functional glycodiversity
    • Benito J.M., Ortega-Caballero F. Recent developments on synthetic tools towards structural and functional glycodiversity. Curr. Med. Chem. 2013, 20:3986-4029.
    • (2013) Curr. Med. Chem. , vol.20 , pp. 3986-4029
    • Benito, J.M.1    Ortega-Caballero, F.2
  • 9
    • 33744523569 scopus 로고    scopus 로고
    • Enzymatic tools for engineering natural product glycosylation
    • Blanchard S., Thorson J.S. Enzymatic tools for engineering natural product glycosylation. Curr. Opin. Chem. Biol. 2006, 10:263-271.
    • (2006) Curr. Opin. Chem. Biol. , vol.10 , pp. 263-271
    • Blanchard, S.1    Thorson, J.S.2
  • 10
    • 57049185719 scopus 로고    scopus 로고
    • Engineering natural products using combinatorial biosynthesis and biocatalysis
    • Zhou H., Xie X., Tang Y. Engineering natural products using combinatorial biosynthesis and biocatalysis. Curr. Opin. Biotechnol. 2008, 19:590-596.
    • (2008) Curr. Opin. Biotechnol. , vol.19 , pp. 590-596
    • Zhou, H.1    Xie, X.2    Tang, Y.3
  • 11
    • 0035501490 scopus 로고    scopus 로고
    • Altering the glycosylation pattern of bioactive compounds
    • Méndez C., Salas J.A. Altering the glycosylation pattern of bioactive compounds. Trends Biotechnol. 2001, 19:449-456.
    • (2001) Trends Biotechnol. , vol.19 , pp. 449-456
    • Méndez, C.1    Salas, J.A.2
  • 12
    • 0032400815 scopus 로고    scopus 로고
    • Flavonoids: dietary occurrence and biochemical activity
    • Peterson J., Dwyer J. Flavonoids: dietary occurrence and biochemical activity. Nutr. Res. 1998, 18:1995-2018.
    • (1998) Nutr. Res. , vol.18 , pp. 1995-2018
    • Peterson, J.1    Dwyer, J.2
  • 13
    • 0033637140 scopus 로고    scopus 로고
    • The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer
    • Middleton Kandaswami E.C., Theoharides T.C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 2000, 52:673-751.
    • (2000) Pharmacol. Rev. , vol.52 , pp. 673-751
    • Middleton Kandaswami, E.C.1    Theoharides, T.C.2
  • 14
    • 0036400016 scopus 로고    scopus 로고
    • Dietary flavonoids: bioavailability metabolic effects, and Safety
    • Ross J.A., Kasum C.M. Dietary flavonoids: bioavailability metabolic effects, and Safety. Annu. Rev. Nutr. 2002, 22:19-34.
    • (2002) Annu. Rev. Nutr. , vol.22 , pp. 19-34
    • Ross, J.A.1    Kasum, C.M.2
  • 15
    • 35748966709 scopus 로고    scopus 로고
    • Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: chemical diversity, impacts on plant biology and human health
    • Ververidis F., Trantas E., Douglas C., Vollmer G., Kretzschmar G., Panopoulos N. Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: chemical diversity, impacts on plant biology and human health. Biotechnol. J. 2007, 2:1214-1234.
    • (2007) Biotechnol. J. , vol.2 , pp. 1214-1234
    • Ververidis, F.1    Trantas, E.2    Douglas, C.3    Vollmer, G.4    Kretzschmar, G.5    Panopoulos, N.6
  • 16
    • 84880810277 scopus 로고    scopus 로고
    • Regiospecific modifications of naringenin for astragalin production in Escherichia coli
    • Malla S., Pandey R.P., Kim B.G., Sohng J.K. Regiospecific modifications of naringenin for astragalin production in Escherichia coli. Biotechnol. Bioeng. 2013, 110:2525-2535.
    • (2013) Biotechnol. Bioeng. , vol.110 , pp. 2525-2535
    • Malla, S.1    Pandey, R.P.2    Kim, B.G.3    Sohng, J.K.4
  • 17
    • 72449122772 scopus 로고    scopus 로고
    • Metabolic engineering of Escherichia coli for the biological synthesis of 7-O-xylosyl naringenin
    • Simkhada D., Kim E.M., Lee H.C., Sohng J.K. Metabolic engineering of Escherichia coli for the biological synthesis of 7-O-xylosyl naringenin. Mol. Cells 2009, 28:397-401.
    • (2009) Mol. Cells , vol.28 , pp. 397-401
    • Simkhada, D.1    Kim, E.M.2    Lee, H.C.3    Sohng, J.K.4
  • 19
    • 77956260624 scopus 로고    scopus 로고
    • Genetic engineering approach for the production of rhamnosyl and allosyl flavonoids from Escherichia coli
    • Simkhada D., Lee H.C., Sohng J.K. Genetic engineering approach for the production of rhamnosyl and allosyl flavonoids from Escherichia coli. Biotechnol. Bioeng. 2010, 107:154-162.
    • (2010) Biotechnol. Bioeng. , vol.107 , pp. 154-162
    • Simkhada, D.1    Lee, H.C.2    Sohng, J.K.3
  • 20
    • 84864086262 scopus 로고    scopus 로고
    • Production of a novel quercetin glycoside through metabolic engineering of Escherichia coli
    • Yoon J.A., Kim B.G., Lee W.J., Lim Y., Chong Y., Ahn J.H. Production of a novel quercetin glycoside through metabolic engineering of Escherichia coli. Appl. Environ. Microbiol. 2012, 78:4256-4262.
    • (2012) Appl. Environ. Microbiol. , vol.78 , pp. 4256-4262
    • Yoon, J.A.1    Kim, B.G.2    Lee, W.J.3    Lim, Y.4    Chong, Y.5    Ahn, J.H.6
  • 21
    • 84898637544 scopus 로고    scopus 로고
    • Synthesis of flavonoid O-pentosides by Escherichia coli through engineering of nucleotide sugar pathways and glycosyltransferase
    • Han S.H., Kim B.G., Yoon J.A., Chong Y., Ahn J.H. Synthesis of flavonoid O-pentosides by Escherichia coli through engineering of nucleotide sugar pathways and glycosyltransferase. Appl. Environ. Microbiol. 2014, 80:2754-2762.
    • (2014) Appl. Environ. Microbiol. , vol.80 , pp. 2754-2762
    • Han, S.H.1    Kim, B.G.2    Yoon, J.A.3    Chong, Y.4    Ahn, J.H.5
  • 22
    • 84862291189 scopus 로고    scopus 로고
    • Biological synthesis of quercetin 3-O-N-acetylglucosamine conjugate using engineered Escherichia coli expressing UGT78D2
    • Kim B.G., Sung S.H., Ahn J.H. Biological synthesis of quercetin 3-O-N-acetylglucosamine conjugate using engineered Escherichia coli expressing UGT78D2. Appl. Microbiol. Biotechnol. 2011, 93:2447-2453.
    • (2011) Appl. Microbiol. Biotechnol. , vol.93 , pp. 2447-2453
    • Kim, B.G.1    Sung, S.H.2    Ahn, J.H.3
  • 23
    • 84890126310 scopus 로고    scopus 로고
    • Biocatalytic synthesis of quercetin 3-O-glucoside-7-O-rhamnoside by metabolic engineering of Escherichia coli
    • Roepke J., Bozzo G.G. Biocatalytic synthesis of quercetin 3-O-glucoside-7-O-rhamnoside by metabolic engineering of Escherichia coli. Chembiochem 2013, 14:2418-2422.
    • (2013) Chembiochem , vol.14 , pp. 2418-2422
    • Roepke, J.1    Bozzo, G.G.2
  • 24
    • 0034612342 scopus 로고    scopus 로고
    • One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products
    • Datsenko K.A., Wanner B.L. One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc. Natl. Acad. Sci. U. S. A. 2000, 97:6640-6645.
    • (2000) Proc. Natl. Acad. Sci. U. S. A. , vol.97 , pp. 6640-6645
    • Datsenko, K.A.1    Wanner, B.L.2
  • 26
    • 34250672787 scopus 로고    scopus 로고
    • Enzymatic synthesis of dTDP-4-amino-4,6-dideoxy-D-glucose using gerb (dTDP-4-keto-6-deoxy-D-glucose aminotransferase)
    • Chung Y.S., Kim D.H., Seo W.M., Lee H.C., Liou K., Oh T.J., Sohng J.K. Enzymatic synthesis of dTDP-4-amino-4,6-dideoxy-D-glucose using gerb (dTDP-4-keto-6-deoxy-D-glucose aminotransferase). Carbohydr. Res. 2007, 342:1412-1418.
    • (2007) Carbohydr. Res. , vol.342 , pp. 1412-1418
    • Chung, Y.S.1    Kim, D.H.2    Seo, W.M.3    Lee, H.C.4    Liou, K.5    Oh, T.J.6    Sohng, J.K.7
  • 27
    • 3342987492 scopus 로고    scopus 로고
    • Characterization and investigation of substrate specificity of the sugar aminotransferase wece from E. coli K12
    • Hwang B.Y., Lee H.J., Yang Y.H., Joo H.S., Kim B.G. Characterization and investigation of substrate specificity of the sugar aminotransferase wece from E. coli K12. Chem. Biol. 2004, 11:915-925.
    • (2004) Chem. Biol. , vol.11 , pp. 915-925
    • Hwang, B.Y.1    Lee, H.J.2    Yang, Y.H.3    Joo, H.S.4    Kim, B.G.5
  • 28
    • 0038374382 scopus 로고    scopus 로고
    • Biosynthesis of dTDP-3-acetamido-3,6 dideoxy-alpha-D-galactose in aneurinibacillus thermoaerophilus L420-91T
    • Pfoestl A., Hofinger A., Kosma P., Messner P. Biosynthesis of dTDP-3-acetamido-3,6 dideoxy-alpha-D-galactose in aneurinibacillus thermoaerophilus L420-91T. J. Biol. Chem. 2003, 278:26410-26417.
    • (2003) J. Biol. Chem. , vol.278 , pp. 26410-26417
    • Pfoestl, A.1    Hofinger, A.2    Kosma, P.3    Messner, P.4
  • 29
    • 33745261717 scopus 로고    scopus 로고
    • Reconstruction of de novo pathway for synthesis of UDP-glucoronic acid and UDP-xylose from intrinsic UDP-glucose in Saccharomyces cerevisiae
    • Oka T., Jigami Y. Reconstruction of de novo pathway for synthesis of UDP-glucoronic acid and UDP-xylose from intrinsic UDP-glucose in Saccharomyces cerevisiae. FEBS J. 2006, 273:2645-2657.
    • (2006) FEBS J. , vol.273 , pp. 2645-2657
    • Oka, T.1    Jigami, Y.2
  • 30
    • 0035497394 scopus 로고    scopus 로고
    • Analysis of nucleotide sugars from cell lysates by ion-pair solid-phase extraction and reversed-phase high-performance liquid chromatography
    • Räbinä J., Mäki M., Savilahti E.M., Järvinen N., Penttilä L., Renkonen R. Analysis of nucleotide sugars from cell lysates by ion-pair solid-phase extraction and reversed-phase high-performance liquid chromatography. Glycoconj. J. 2001, 18:799-805.
    • (2001) Glycoconj. J. , vol.18 , pp. 799-805
    • Räbinä, J.1    Mäki, M.2    Savilahti, E.M.3    Järvinen, N.4    Penttilä, L.5    Renkonen, R.6
  • 31
    • 0242498474 scopus 로고    scopus 로고
    • UGT73C6 and UGT78D1, glycosyltransferases involved in flavonol glycoside biosynthesis in arabidopsis thaliana
    • Jones P., Messner B., Nakajima J., Schäffner A.R., Saito K. UGT73C6 and UGT78D1, glycosyltransferases involved in flavonol glycoside biosynthesis in arabidopsis thaliana. J. Biol. Chem. 2003, 278:43910-43918.
    • (2003) J. Biol. Chem. , vol.278 , pp. 43910-43918
    • Jones, P.1    Messner, B.2    Nakajima, J.3    Schäffner, A.R.4    Saito, K.5
  • 32
    • 84925534165 scopus 로고    scopus 로고
    • Biosynthesis and production of glycosylated flavonoids in Escherichia coli: current state and perspectives
    • Kim B.G., Yang S.M., Kim S.Y., Cha M.N., Ahn J.H. Biosynthesis and production of glycosylated flavonoids in Escherichia coli: current state and perspectives. Appl. Microbiol. Biotechnol. 2015, 99:2979-2988.
    • (2015) Appl. Microbiol. Biotechnol. , vol.99 , pp. 2979-2988
    • Kim, B.G.1    Yang, S.M.2    Kim, S.Y.3    Cha, M.N.4    Ahn, J.H.5
  • 33
    • 84922895084 scopus 로고    scopus 로고
    • Microbial biotransformation of bioactive flavonoids
    • Cao H., Chen X., Jassbi A.R., Xiao J. Microbial biotransformation of bioactive flavonoids. Biotechnol. Adv. 2015, pii S0734-9750(14)161-X.
    • (2015) Biotechnol. Adv.
    • Cao, H.1    Chen, X.2    Jassbi, A.R.3    Xiao, J.4
  • 34
    • 84921699683 scopus 로고    scopus 로고
    • Flavonoid glycosylation and biological benefits
    • (b)
    • Xiao J., Chen T., Cao H. Flavonoid glycosylation and biological benefits. Biotechnol. Adv. 2014, S0734-S9750. pii S0734-9750(14) 92-5. (b).
    • (2014) Biotechnol. Adv. , pp. S0734-S9750
    • Xiao, J.1    Chen, T.2    Cao, H.3
  • 35
    • 79958126727 scopus 로고    scopus 로고
    • Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models
    • Pedersen C.M., Olsen J., Brka A.B., Biols M. Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models. Chem. Eur. J. 2011, 17:7080-7086.
    • (2011) Chem. Eur. J. , vol.17 , pp. 7080-7086
    • Pedersen, C.M.1    Olsen, J.2    Brka, A.B.3    Biols, M.4
  • 36
    • 0347384092 scopus 로고    scopus 로고
    • Thorson Antibiotic optimization via in vitro glycorandomization
    • Fu X., Albermann C., Jiang J., Liao J., Zhang C., Thorson Antibiotic optimization via in vitro glycorandomization. Nat. Biotechnol. 2003, 21:1467-1469.
    • (2003) Nat. Biotechnol. , vol.21 , pp. 1467-1469
    • Fu, X.1    Albermann, C.2    Jiang, J.3    Liao, J.4    Zhang, C.5
  • 38
    • 79952590274 scopus 로고    scopus 로고
    • Probing the role of the mycosamine C2'-OH on the activity of amphotericin B
    • Croatt M.P., Carreira E.M. Probing the role of the mycosamine C2'-OH on the activity of amphotericin B. Org. Lett 2011, 13:1390-1393.
    • (2011) Org. Lett , vol.13 , pp. 1390-1393
    • Croatt, M.P.1    Carreira, E.M.2
  • 39
    • 84872382324 scopus 로고    scopus 로고
    • Aminoglyco-sylation can enhance the G-quadruplex binding activity of epigallocatechin
    • Bai L.P., Ho H.M., Ma D.L., Yang H., Fu W.C., Jiang Z.H. Aminoglyco-sylation can enhance the G-quadruplex binding activity of epigallocatechin. Plos ONE 2013, 8:e53962.
    • (2013) Plos ONE , vol.8 , pp. e53962
    • Bai, L.P.1    Ho, H.M.2    Ma, D.L.3    Yang, H.4    Fu, W.C.5    Jiang, Z.H.6
  • 41
    • 84863824452 scopus 로고    scopus 로고
    • A peptide nucleic acid-aminosugar conjugate targeting transactivation response element of HIV-1 RNA genome shows a high bioavailability in human cells and strongly inhibits tat-mediated transactivation of HIV-1 transcription
    • Das I., Desire J., Manvar D., Baussanne I., Pandey V.N., Decout J.L. A peptide nucleic acid-aminosugar conjugate targeting transactivation response element of HIV-1 RNA genome shows a high bioavailability in human cells and strongly inhibits tat-mediated transactivation of HIV-1 transcription. J. Med. Chem. 2012, 55:6021-6032.
    • (2012) J. Med. Chem. , vol.55 , pp. 6021-6032
    • Das, I.1    Desire, J.2    Manvar, D.3    Baussanne, I.4    Pandey, V.N.5    Decout, J.L.6
  • 42
    • 84928905615 scopus 로고    scopus 로고
    • Quercetin in prostate cancer: chemotherapeutic and chemopreventive effects, mechanisms and clinical application potential (review)
    • Yang F., Song L., Wang H., Wang J., Xu Z., Xing N. Quercetin in prostate cancer: chemotherapeutic and chemopreventive effects, mechanisms and clinical application potential (review). Oncol. Rep. 2015, 10.3892/or.2015.3886.
    • (2015) Oncol. Rep.
    • Yang, F.1    Song, L.2    Wang, H.3    Wang, J.4    Xu, Z.5    Xing, N.6
  • 43
    • 84893720574 scopus 로고    scopus 로고
    • Anti-cancer effect and underlying mechanism(s) of kaempferol, a phytoestrogen, on the regulation of apoptosis in diverse cancer cell models
    • Kim S.H., Choi K.C. Anti-cancer effect and underlying mechanism(s) of kaempferol, a phytoestrogen, on the regulation of apoptosis in diverse cancer cell models. Toxicol. Res. 2013, 29:229-234.
    • (2013) Toxicol. Res. , vol.29 , pp. 229-234
    • Kim, S.H.1    Choi, K.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.