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Volumn 191, Issue , 2014, Pages 69-77

One-step synthesis of 2-keto-3-deoxy-D-gluconate by biocatalytic dehydration of D-gluconate

Author keywords

2 Keto 3 deoxy d gluconate; Biocatalytic dehydration; Gluconate dehydratase; LC MS; Metabolite

Indexed keywords

METABOLISM; METABOLITES; STEREOCHEMISTRY;

EID: 84912035051     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2014.06.005     Document Type: Article
Times cited : (23)

References (44)
  • 1
    • 25144485326 scopus 로고    scopus 로고
    • The semi-phosphorylative Entner-Doudoroff pathway in hyperthermophilic archaea: a re-evaluation
    • Ahmed H., Ettema T.J., Tjaden B., Geerling A.C., van der Oost J., Siebers B. The semi-phosphorylative Entner-Doudoroff pathway in hyperthermophilic archaea: a re-evaluation. Biochem. J. 2005, 390:529-540.
    • (2005) Biochem. J. , vol.390 , pp. 529-540
    • Ahmed, H.1    Ettema, T.J.2    Tjaden, B.3    Geerling, A.C.4    van der Oost, J.5    Siebers, B.6
  • 2
    • 0014652956 scopus 로고
    • The occurrence of a modified Entner-Doudoroff pathway in Clostridium aceticum
    • Andreesen J., Gottschalk G. The occurrence of a modified Entner-Doudoroff pathway in Clostridium aceticum. Arch. Microbiol. 1969, 69:160-170.
    • (1969) Arch. Microbiol. , vol.69 , pp. 160-170
    • Andreesen, J.1    Gottschalk, G.2
  • 3
    • 0027288859 scopus 로고
    • Microbiological aldolisations: synthesis of 2-keto-3-deoxy-d-gluconate
    • Augé C., Delest V. Microbiological aldolisations: synthesis of 2-keto-3-deoxy-d-gluconate. Tetrahedron Asymmetr 1993, 4:1165-1168.
    • (1993) Tetrahedron Asymmetr , vol.4 , pp. 1165-1168
    • Augé, C.1    Delest, V.2
  • 5
    • 84980118812 scopus 로고
    • Zur synthese von 3-desoxy-aldulosonsäuren
    • Baschang G., Fritz H. Zur synthese von 3-desoxy-aldulosonsäuren. Helv. Chim. Acta 1969, 52:300-305.
    • (1969) Helv. Chim. Acta , vol.52 , pp. 300-305
    • Baschang, G.1    Fritz, H.2
  • 6
    • 0015102449 scopus 로고
    • 2-Keto-3-deoxygluconate, an intermediate in the fermentation of gluconate by clostridia
    • Bender R., Andreesen J., Gottschalk G. 2-Keto-3-deoxygluconate, an intermediate in the fermentation of gluconate by clostridia. J. Bacteriol. 1971, 107:570-573.
    • (1971) J. Bacteriol. , vol.107 , pp. 570-573
    • Bender, R.1    Andreesen, J.2    Gottschalk, G.3
  • 7
    • 0015737509 scopus 로고
    • Purification and properties of d-gluconate dehydratase from Clostridium pasteurianum
    • Bender R., Gottschalk G. Purification and properties of d-gluconate dehydratase from Clostridium pasteurianum. Eur. J. Biochem. 1973, 40:309-321.
    • (1973) Eur. J. Biochem. , vol.40 , pp. 309-321
    • Bender, R.1    Gottschalk, G.2
  • 8
    • 84912019259 scopus 로고
    • Enzymatic synthesis of 2-keto-3-deoxy-d-glucose from d-gluconate
    • Bender R., Gottschalk G. Enzymatic synthesis of 2-keto-3-deoxy-d-glucose from d-gluconate. Anal. Biochem. 1974, 61:9.
    • (1974) Anal. Biochem. , vol.61 , pp. 9
    • Bender, R.1    Gottschalk, G.2
  • 9
    • 84896282192 scopus 로고    scopus 로고
    • Carbohydrate metabolism in archaea: current insights into unusual enzymes and pathways and their regulation
    • Bräsen C., Esser D., Rauch B., Siebers B. Carbohydrate metabolism in archaea: current insights into unusual enzymes and pathways and their regulation. Microbiol. Mol. Biol. Rev. 2014, 78:89-175.
    • (2014) Microbiol. Mol. Biol. Rev. , vol.78 , pp. 89-175
    • Bräsen, C.1    Esser, D.2    Rauch, B.3    Siebers, B.4
  • 10
    • 0033229936 scopus 로고    scopus 로고
    • An extremely thermostable aldolase from Sulfolobus solfataricus with specificity for non-phosphorylated substrates
    • Buchanan C., Connaris H., Danson M., Reeve C., Hough D. An extremely thermostable aldolase from Sulfolobus solfataricus with specificity for non-phosphorylated substrates. Biochem. J. 1999, 343:563-570.
    • (1999) Biochem. J. , vol.343 , pp. 563-570
    • Buchanan, C.1    Connaris, H.2    Danson, M.3    Reeve, C.4    Hough, D.5
  • 11
    • 0014687797 scopus 로고
    • 2-Keto-3-deoxyl-l-arabonate aldolase and its role in a new pathway of l-arabinose degradation
    • Dahms A.S., Anderson R.L. 2-Keto-3-deoxyl-l-arabonate aldolase and its role in a new pathway of l-arabinose degradation. Biochem. Biophys. Res. Commun. 1969, 36:809-814.
    • (1969) Biochem. Biophys. Res. Commun. , vol.36 , pp. 809-814
    • Dahms, A.S.1    Anderson, R.L.2
  • 12
    • 84875748374 scopus 로고    scopus 로고
    • Biomimetic direct aldol reaction of pyruvate esters with chiral aldehydes
    • El-Sepelgy O., Mlynarski J. Biomimetic direct aldol reaction of pyruvate esters with chiral aldehydes. Adv. Synth. Catal. 2013, 355:281-286.
    • (2013) Adv. Synth. Catal. , vol.355 , pp. 281-286
    • El-Sepelgy, O.1    Mlynarski, J.2
  • 13
    • 84860637583 scopus 로고    scopus 로고
    • Direct aldol reaction of pyruvic derivatives: catalytic attempt to synthesize ulosonic acids
    • El-Sepelgy O., Schwarzer D., Oskwarek P., Mlynarski J. Direct aldol reaction of pyruvic derivatives: catalytic attempt to synthesize ulosonic acids. Eur. J. Org. Chem. 2012, 2012:2724-2727.
    • (2012) Eur. J. Org. Chem. , vol.2012 , pp. 2724-2727
    • El-Sepelgy, O.1    Schwarzer, D.2    Oskwarek, P.3    Mlynarski, J.4
  • 14
    • 0015609412 scopus 로고
    • New pathway for nonphosphorylated degradation of gluconate by Aspergillus niger
    • Elzainy T., Hassan M., Allam A. New pathway for nonphosphorylated degradation of gluconate by Aspergillus niger. J. Bacteriol. 1973, 114:457-459.
    • (1973) J. Bacteriol. , vol.114 , pp. 457-459
    • Elzainy, T.1    Hassan, M.2    Allam, A.3
  • 15
    • 33845495393 scopus 로고    scopus 로고
    • Proline organocatalysis as a new tool for the asymmetric synthesis of ulosonic acid precursors
    • Enders D., Gasperi T. Proline organocatalysis as a new tool for the asymmetric synthesis of ulosonic acid precursors. Chem Commun. 2007, 88-90.
    • (2007) Chem Commun. , pp. 88-90
    • Enders, D.1    Gasperi, T.2
  • 16
    • 76949122636 scopus 로고
    • Glucose and gluconic acid oxidation of Pseudomonas saccharophila
    • Entner N., Doudoroff M. Glucose and gluconic acid oxidation of Pseudomonas saccharophila. J. Biol. Chem. 1952, 196:853-862.
    • (1952) J. Biol. Chem. , vol.196 , pp. 853-862
    • Entner, N.1    Doudoroff, M.2
  • 17
    • 0020701677 scopus 로고
    • Chemolithoautotrophic metabolism of anaerobic extremely thermophilic archaebacteria
    • Fischer F., Zillig W., Stetter K., Schreiber G. Chemolithoautotrophic metabolism of anaerobic extremely thermophilic archaebacteria. Nature 1983, 301:511-513.
    • (1983) Nature , vol.301 , pp. 511-513
    • Fischer, F.1    Zillig, W.2    Stetter, K.3    Schreiber, G.4
  • 18
    • 0033768504 scopus 로고    scopus 로고
    • Directed evolution of d-2-keto-3-deoxy-6-phosphogluconate aldolase to new variants for the efficient synthesis of d- and l-sugars
    • Fong S., Machajewski T.D., Mak C.C., Wong C.-H. Directed evolution of d-2-keto-3-deoxy-6-phosphogluconate aldolase to new variants for the efficient synthesis of d- and l-sugars. Chem. Biol. 2000, 7:873-883.
    • (2000) Chem. Biol. , vol.7 , pp. 873-883
    • Fong, S.1    Machajewski, T.D.2    Mak, C.C.3    Wong, C.-H.4
  • 19
    • 84855286291 scopus 로고    scopus 로고
    • Divergent evolution in enolase superfamily: strategies for assigning functions
    • Gerlt J.A., Babbitt P.C., Jacobson M.P., Almo S.C. Divergent evolution in enolase superfamily: strategies for assigning functions. J. Biol. Chem. 2012, 287:29-34.
    • (2012) J. Biol. Chem. , vol.287 , pp. 29-34
    • Gerlt, J.A.1    Babbitt, P.C.2    Jacobson, M.P.3    Almo, S.C.4
  • 20
    • 0016415597 scopus 로고
    • D-Gluconate dehydratase from Alcaligenes
    • Kersters K., De Ley J. d-Gluconate dehydratase from Alcaligenes. Methods Enzymol. 1974, 42:301-304.
    • (1974) Methods Enzymol. , vol.42 , pp. 301-304
    • Kersters, K.1    De Ley, J.2
  • 22
    • 17144427281 scopus 로고    scopus 로고
    • Identification and characterization of Sulfolobus solfataricus d-gluconate dehydratase: a key enzyme in the non-phosphorylated Entner-Doudoroff pathway
    • Kim S., Lee S. Identification and characterization of Sulfolobus solfataricus d-gluconate dehydratase: a key enzyme in the non-phosphorylated Entner-Doudoroff pathway. Biochem. J. 2005, 387:271-280.
    • (2005) Biochem. J. , vol.387 , pp. 271-280
    • Kim, S.1    Lee, S.2
  • 23
    • 12744261280 scopus 로고    scopus 로고
    • Engineering stereocontrol into an aldolase-catalysed reaction
    • Lamble H.J., Danson M.J., Hough D.W., Bull S.D. Engineering stereocontrol into an aldolase-catalysed reaction. Chem. Commun. 2005, 124-126.
    • (2005) Chem. Commun. , pp. 124-126
    • Lamble, H.J.1    Danson, M.J.2    Hough, D.W.3    Bull, S.D.4
  • 24
    • 0141483333 scopus 로고    scopus 로고
    • Metabolic pathway promiscuity in the archaeon Sulfolobus solfataricus revealed by studies on glucose dehydrogenase and 2-keto-3-deoxygluconate aldolase
    • Lamble H.J., Heyer N.I., Bull S.D., Hough D.W., Danson M.J. Metabolic pathway promiscuity in the archaeon Sulfolobus solfataricus revealed by studies on glucose dehydrogenase and 2-keto-3-deoxygluconate aldolase. J. Biol. Chem. 2003, 278:34066-34072.
    • (2003) J. Biol. Chem. , vol.278 , pp. 34066-34072
    • Lamble, H.J.1    Heyer, N.I.2    Bull, S.D.3    Hough, D.W.4    Danson, M.J.5
  • 25
    • 4944251746 scopus 로고    scopus 로고
    • Gluconate dehydratase from the promiscuous Entner-Doudoroff pathway in Sulfolobus solfataricus
    • Lamble H.J., Milburn C.C., Taylor G.L., Hough D.W., Danson M.J. Gluconate dehydratase from the promiscuous Entner-Doudoroff pathway in Sulfolobus solfataricus. FEBS Lett. 2004, 576:133-136.
    • (2004) FEBS Lett. , vol.576 , pp. 133-136
    • Lamble, H.J.1    Milburn, C.C.2    Taylor, G.L.3    Hough, D.W.4    Danson, M.J.5
  • 26
    • 34250128476 scopus 로고
    • Production of 2-keto-3-deoxygluconate by immobilized cells of Sulfolobus solfataricus
    • Nicolaus B., de Simone A., del Pinao L., Giardina P., Lama L. Production of 2-keto-3-deoxygluconate by immobilized cells of Sulfolobus solfataricus. Biotechnol. Lett. 1986, 8:497-500.
    • (1986) Biotechnol. Lett. , vol.8 , pp. 497-500
    • Nicolaus, B.1    de Simone, A.2    del Pinao, L.3    Giardina, P.4    Lama, L.5
  • 28
    • 0000077155 scopus 로고
    • Nouvelle synthese de l'acide 3-desoxy-d-erythro-2-hexulosonique (KDG). A partir de la d-glucono-1,5-lactone synthese et etude de RMN de derives O-methyles du KDG
    • Plantier-Royon R., Cardona F., Anker D., Condemine G., Nasser W., Robert-Baudouy J. Nouvelle synthese de l'acide 3-desoxy-d-erythro-2-hexulosonique (KDG). A partir de la d-glucono-1,5-lactone synthese et etude de RMN de derives O-methyles du KDG. J. Carbohydr. Chem. 1991, 10:787-811.
    • (1991) J. Carbohydr. Chem. , vol.10 , pp. 787-811
    • Plantier-Royon, R.1    Cardona, F.2    Anker, D.3    Condemine, G.4    Nasser, W.5    Robert-Baudouy, J.6
  • 29
    • 0001093981 scopus 로고
    • Synthesis and properties of 3,6-dideoxyhexulosonic acids and related compounds: a convenient preparation of 3-deoxy-d-erythro-hexulosonic acid (3-deoxy-2-keto-d-gluconic acid). Stereoselectivity of nucleophilic addition to triose carbonyl
    • Portsmouth D. Synthesis and properties of 3,6-dideoxyhexulosonic acids and related compounds: a convenient preparation of 3-deoxy-d-erythro-hexulosonic acid (3-deoxy-2-keto-d-gluconic acid). Stereoselectivity of nucleophilic addition to triose carbonyl. Carbohydr. Res. 1968, 8:193-204.
    • (1968) Carbohydr. Res. , vol.8 , pp. 193-204
    • Portsmouth, D.1
  • 30
    • 0025775820 scopus 로고
    • Dioxalanones as synthetic intermediates Part 6. Synthesis of 3-deoxy-d-manno-2-octulosonic acid (KDO), 3-deoxy-d-arabino-2-heptulosonic acid (DAH) and 2-keto-3-deoxy-d-gluconic acid (KDG)
    • Ramage R., MacLeod A.M., Rose G.W. Dioxalanones as synthetic intermediates Part 6. Synthesis of 3-deoxy-d-manno-2-octulosonic acid (KDO), 3-deoxy-d-arabino-2-heptulosonic acid (DAH) and 2-keto-3-deoxy-d-gluconic acid (KDG). Tetrahedron 1991, 47:5625-5636.
    • (1991) Tetrahedron , vol.47 , pp. 5625-5636
    • Ramage, R.1    MacLeod, A.M.2    Rose, G.W.3
  • 31
    • 75749149349 scopus 로고    scopus 로고
    • The nonphosphorylative Entner-Doudoroff pathway in the thermoacidophilic euryarchaeon Picrophilus torridus involves a novel 2-keto-3-deoxygluconate-specific aldolase
    • Reher M., Fuhrer T., Bott M., Schönheit P. The nonphosphorylative Entner-Doudoroff pathway in the thermoacidophilic euryarchaeon Picrophilus torridus involves a novel 2-keto-3-deoxygluconate-specific aldolase. J. Bacteriol. 2010, 192:964-974.
    • (2010) J. Bacteriol. , vol.192 , pp. 964-974
    • Reher, M.1    Fuhrer, T.2    Bott, M.3    Schönheit, P.4
  • 32
    • 0031002263 scopus 로고    scopus 로고
    • Comparative analysis of Embden-Meyerhof and Entner-Doudoroff glycolytic pathways in hyperthermophilic archaea and the bacterium Thermotoga
    • Selig M., Xavier K.B., Santos H., Schönheit P. Comparative analysis of Embden-Meyerhof and Entner-Doudoroff glycolytic pathways in hyperthermophilic archaea and the bacterium Thermotoga. Arch. Microbiol. 1997, 167:217-232.
    • (1997) Arch. Microbiol. , vol.167 , pp. 217-232
    • Selig, M.1    Xavier, K.B.2    Santos, H.3    Schönheit, P.4
  • 33
    • 1542499810 scopus 로고    scopus 로고
    • Carbonyl-ene approach to the asymmetric synthesis of 2-keto-3-deoxy-d-gluconic acid (KDG): a combinatorial sequence using sharpless epoxidation
    • Shimizu M., Yoshida A., Mikami K. Carbonyl-ene approach to the asymmetric synthesis of 2-keto-3-deoxy-d-gluconic acid (KDG): a combinatorial sequence using sharpless epoxidation. Synlett 1996, 1996:1112-1114.
    • (1996) Synlett , vol.1996 , pp. 1112-1114
    • Shimizu, M.1    Yoshida, A.2    Mikami, K.3
  • 34
    • 0027249393 scopus 로고
    • Glucose catabolism of the hyperthermophilic archaeum Thermoproteus tenax
    • Siebers B., Hensel R. Glucose catabolism of the hyperthermophilic archaeum Thermoproteus tenax. FEMS Microbiol. Lett. 1993, 111:1-7.
    • (1993) FEMS Microbiol. Lett. , vol.111 , pp. 1-7
    • Siebers, B.1    Hensel, R.2
  • 36
    • 0030871983 scopus 로고    scopus 로고
    • Carbohydrate metabolism in Thermoproteus tenax: in vivo utilization of the non-phosphorylative Entner-Doudoroff pathway and characterization of its first enzyme, glucose dehydrogenase
    • Siebers B., Wendisch V.F., Hensel R. Carbohydrate metabolism in Thermoproteus tenax: in vivo utilization of the non-phosphorylative Entner-Doudoroff pathway and characterization of its first enzyme, glucose dehydrogenase. Arch. Microbiol. 1997, 168:120-127.
    • (1997) Arch. Microbiol. , vol.168 , pp. 120-127
    • Siebers, B.1    Wendisch, V.F.2    Hensel, R.3
  • 37
    • 0007522911 scopus 로고
    • Carbohydrate metabolism in Rhodopseudomonas spheroides
    • Szymona M., Doudoroff M. Carbohydrate metabolism in Rhodopseudomonas spheroides. J. Gen. Microbiol. 1960, 22:167-183.
    • (1960) J. Gen. Microbiol. , vol.22 , pp. 167-183
    • Szymona, M.1    Doudoroff, M.2
  • 38
  • 39
    • 6344289413 scopus 로고    scopus 로고
    • The structural basis for substrate promiscuity in 2-keto-3-deoxygluconate aldolase from the Entner-Doudoroff pathway in Sulfolobus solfataricus
    • Theodossis A., Walden H., Westwick E.J., Connaris H., Lamble H.J., Hough D.W., Danson M.J., Taylor G.L. The structural basis for substrate promiscuity in 2-keto-3-deoxygluconate aldolase from the Entner-Doudoroff pathway in Sulfolobus solfataricus. J. Biol. Chem. 2004, 279:43886-43892.
    • (2004) J. Biol. Chem. , vol.279 , pp. 43886-43892
    • Theodossis, A.1    Walden, H.2    Westwick, E.J.3    Connaris, H.4    Lamble, H.J.5    Hough, D.W.6    Danson, M.J.7    Taylor, G.L.8
  • 40
    • 34147150667 scopus 로고    scopus 로고
    • Potential and utilization of thermophiles and thermostable enzymes in biorefining
    • Turner P., Mamo G., Karlsson E.N. Potential and utilization of thermophiles and thermostable enzymes in biorefining. Microb. Cell. Fact. 2007, 6:1-23.
    • (2007) Microb. Cell. Fact. , vol.6 , pp. 1-23
    • Turner, P.1    Mamo, G.2    Karlsson, E.N.3
  • 41
    • 0003211068 scopus 로고
    • The oxidation of l-arabinose by Pseudomonas saccharophila
    • Weimberg R., Doudoroff M. The oxidation of l-arabinose by Pseudomonas saccharophila. J. Biol. Chem. 1955, 217:607-624.
    • (1955) J. Biol. Chem. , vol.217 , pp. 607-624
    • Weimberg, R.1    Doudoroff, M.2
  • 43
    • 49749100770 scopus 로고    scopus 로고
    • The central carbohydrate metabolism of the hyperthermophilic crenarchaeote Thermoproteus tenax: pathways and insights into their regulation
    • Zaparty M., Tjaden B., Hensel R., Siebers B. The central carbohydrate metabolism of the hyperthermophilic crenarchaeote Thermoproteus tenax: pathways and insights into their regulation. Arch. Microbiol. 2008, 190:231-245.
    • (2008) Arch. Microbiol. , vol.190 , pp. 231-245
    • Zaparty, M.1    Tjaden, B.2    Hensel, R.3    Siebers, B.4
  • 44
    • 0019806068 scopus 로고
    • Thermoproteales: a novel type of extremely thermoacidophilic anaerobic archaebacteria isolated from Icelandic solfataras. Zentralblatt für Bakteriologie Mikrobiologie und Hygiene: I. Abt. Originale C: Allgemeine
    • Zillig W., Stetter K., Schäfer W., Janekovic D., Wunderl S., Holz I., Palm P. Thermoproteales: a novel type of extremely thermoacidophilic anaerobic archaebacteria isolated from Icelandic solfataras. Zentralblatt für Bakteriologie Mikrobiologie und Hygiene: I. Abt. Originale C: Allgemeine. Angewandte und ökologische Mikrobiologie 1981, 2:205-227.
    • (1981) Angewandte und ökologische Mikrobiologie , vol.2 , pp. 205-227
    • Zillig, W.1    Stetter, K.2    Schäfer, W.3    Janekovic, D.4    Wunderl, S.5    Holz, I.6    Palm, P.7


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