메뉴 건너뛰기




Volumn 82, Issue 6, 2016, Pages 1706-1721

Enantioselective synthesis of vicinal (R,R)-diols by Saccharomyces cerevisiae butanediol dehydrogenase

Author keywords

[No Author keywords available]

Indexed keywords

COENZYMES; ENZYMES; KETONES; PROTEINS; PURIFICATION; REACTION INTERMEDIATES; STEREOCHEMISTRY;

EID: 84961282551     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.03717-15     Document Type: Article
Times cited : (13)

References (38)
  • 1
    • 82755161073 scopus 로고    scopus 로고
    • Microbial production of diols as platform chemicals: recent progresses
    • Zeng AP, Sabra W. 2011. Microbial production of diols as platform chemicals: recent progresses. Curr Opin Biotechnol 22:749-757. http://dx.doi.org/10.1016/j.copbio.2011.05.005
    • (2011) Curr Opin Biotechnol , vol.22 , pp. 749-757
    • Zeng, A.P.1    Sabra, W.2
  • 2
    • 79952694448 scopus 로고    scopus 로고
    • Microbial 2,3-butanediol production: a state-of-the-art review
    • Ji XJ, Huang H, Ouyang PK. 2011. Microbial 2,3-butanediol production: a state-of-the-art review. Biotechnol Adv 29:351-364. http://dx.doi.org/10.1016/j.biotechadv.2011.01.007
    • (2011) Biotechnol Adv , vol.29 , pp. 351-364
    • Ji, X.J.1    Huang, H.2    Ouyang, P.K.3
  • 3
    • 70349759561 scopus 로고    scopus 로고
    • Biotechnological production of 2,3-butanediol-current state and prospects
    • Celińska E, Grajek W. 2009. Biotechnological production of 2,3-butanediol-current state and prospects. Biotechnol Adv 27:715-725. http://dx.doi.org/10.1016/j.biotechadv.2009.05.002
    • (2009) Biotechnol Adv , vol.27 , pp. 715-725
    • Celińska, E.1    Grajek, W.2
  • 5
    • 84896847314 scopus 로고    scopus 로고
    • Systematic metabolic engineering of Escherichia coli for high-yield production of fuel bio-chemical 2,3-butanediol
    • Xu Y, Chu H, Gao C, Tao F, Zhou Z, Li K, Li L, Ma C, Xu P. 2014. Systematic metabolic engineering of Escherichia coli for high-yield production of fuel bio-chemical 2,3-butanediol. Metab Eng 23:22-33. http://dx.doi.org/10.1016/j.ymben.2014.02.004
    • (2014) Metab Eng , vol.23 , pp. 22-33
    • Xu, Y.1    Chu, H.2    Gao, C.3    Tao, F.4    Zhou, Z.5    Li, K.6    Li, L.7    Ma, C.8    Xu, P.9
  • 6
    • 84939600952 scopus 로고    scopus 로고
    • Enhanced 2,3-butanediol production from biodiesel-derived glycerol by engineering of cofactor regeneration and manipulating carbon flux in Bacillus amyloliquefaciens
    • Yang T, Rao Z, Zhang X, Xu M, Xu Z, Yang ST. 2015. Enhanced 2,3-butanediol production from biodiesel-derived glycerol by engineering of cofactor regeneration and manipulating carbon flux in Bacillus amyloliquefaciens. Microb Cell Fact 14:122. http://dx.doi.org/10.1186/s12934-015-0317-2
    • (2015) Microb Cell Fact , vol.14 , pp. 122
    • Yang, T.1    Rao, Z.2    Zhang, X.3    Xu, M.4    Xu, Z.5    Yang, S.T.6
  • 7
    • 84899893925 scopus 로고    scopus 로고
    • Reconstruction of an acetogenic 2,3-butanediol pathway involving a novel NADPH-dependent primary-secondary alcohol dehydrogenase
    • Köpke M, Gerth ML, Maddock DJ, Mueller AP, Liew F, Simpson SD, Patrick WM. 2014. Reconstruction of an acetogenic 2,3-butanediol pathway involving a novel NADPH-dependent primary-secondary alcohol dehydrogenase. Appl Environ Microbiol 80:3394-3403. http://dx.doi.org/10.1128/AEM.00301-14
    • (2014) Appl Environ Microbiol , vol.80 , pp. 3394-3403
    • Köpke, M.1    Gerth, M.L.2    Maddock, D.J.3    Mueller, A.P.4    Liew, F.5    Simpson, S.D.6    Patrick, W.M.7
  • 8
    • 84882274841 scopus 로고    scopus 로고
    • Production of 2,3-butanediol by engineered Saccharomyces cerevisiae
    • Kim SJ, Seo SO, Jin YS, Seo JH. 2013. Production of 2,3-butanediol by engineered Saccharomyces cerevisiae. Bioresour Technol 146:274-281. http://dx.doi.org/10.1016/j.biortech.2013.07.081
    • (2013) Bioresour Technol , vol.146 , pp. 274-281
    • Kim, S.J.1    Seo, S.O.2    Jin, Y.S.3    Seo, J.H.4
  • 9
    • 84923922989 scopus 로고    scopus 로고
    • Production of 2,3-butanediol from xylose by engineered Saccharomyces cerevisiae
    • Kim SJ, Seo SO, Park YC, Jin YS, Seo JH. 2014. Production of 2,3-butanediol from xylose by engineered Saccharomyces cerevisiae. J Biotechnol 192:376-382. http://dx.doi.org/10.1016/j.jbiotec.2013.12.017
    • (2014) J Biotechnol , vol.192 , pp. 376-382
    • Kim, S.J.1    Seo, S.O.2    Park, Y.C.3    Jin, Y.S.4    Seo, J.H.5
  • 10
    • 0035794283 scopus 로고    scopus 로고
    • Chemoenzymatic preparation of (2S,3S)-and (2R,3R)-2,3-butanediols and their esters from mixtures of D, L-and mesodiols
    • Liu R, Högberg H-E. 2001. Chemoenzymatic preparation of (2S,3S)-and (2R,3R)-2,3-butanediols and their esters from mixtures of D, L-and mesodiols. Tetrahedron Asymmetry 12:771-778. http://dx.doi.org/10.1016/S0957-4166(01)00109-4
    • (2001) Tetrahedron Asymmetry , vol.12 , pp. 771-778
    • Liu, R.1    Högberg, H.-E.2
  • 11
    • 84866183325 scopus 로고    scopus 로고
    • Enhanced fed-batch fermentation of 2,3-butanediol by Paenibacillus polymyxa DSM 365
    • Häßler T, Schieder D, Pfaller R, Faulstich M, Sieber V. 2012. Enhanced fed-batch fermentation of 2,3-butanediol by Paenibacillus polymyxa DSM 365. Bioresour Technol 124:237-244. http://dx.doi.org/10.1016/j.biortech.2012.08.047
    • (2012) Bioresour Technol , vol.124 , pp. 237-244
    • Häßler, T.1    Schieder, D.2    Pfaller, R.3    Faulstich, M.4    Sieber, V.5
  • 12
    • 70349290656 scopus 로고    scopus 로고
    • Enantioselective synthesis of pure (R, R)-2,3-butanediol in Escherichia coli with stereospecific secondary alcohol dehydrogenases
    • Yan Y, Lee CC, Liao JC. 2009. Enantioselective synthesis of pure (R, R)-2,3-butanediol in Escherichia coli with stereospecific secondary alcohol dehydrogenases. Org Biomol Chem 7:3914-3917. http://dx.doi.org/10.1039/b913501d
    • (2009) Org Biomol Chem , vol.7 , pp. 3914-3917
    • Yan, Y.1    Lee, C.C.2    Liao, J.C.3
  • 13
    • 84896297653 scopus 로고    scopus 로고
    • Metabolic engineering of a Saccharomyces cerevisiae strain capable of simultaneously utilizing glucose and galactose to produce enantiopure (2R,3R)-butanediol
    • Lian J, Chao R, Zhao H. 2014. Metabolic engineering of a Saccharomyces cerevisiae strain capable of simultaneously utilizing glucose and galactose to produce enantiopure (2R,3R)-butanediol. Metab Eng 23:92-99. http://dx.doi.org/10.1016/j.ymben.2014.02.003
    • (2014) Metab Eng , vol.23 , pp. 92-99
    • Lian, J.1    Chao, R.2    Zhao, H.3
  • 14
    • 84892544984 scopus 로고    scopus 로고
    • Engineering of cofactor regeneration enhances (2S,3S)-2,3-butanediol production from diacetyl
    • Wang Y, Li L, Ma C, Gao C, Tao F, Xu P. 2013. Engineering of cofactor regeneration enhances (2S,3S)-2,3-butanediol production from diacetyl. Sci Rep 3:2643
    • (2013) Sci Rep , vol.3 , pp. 2643
    • Wang, Y.1    Li, L.2    Ma, C.3    Gao, C.4    Tao, F.5    Xu, P.6
  • 15
    • 77955559433 scopus 로고    scopus 로고
    • Microbial production of meso-2,3-butanediol by metabolically engineered Escherichia coli under low oxygen condition
    • Li ZJ, Jian J, Wei XX, Shen XW, Chen GQ. 2010. Microbial production of meso-2,3-butanediol by metabolically engineered Escherichia coli under low oxygen condition. Appl Microbiol Biotechnol 87:2001-2009. http://dx.doi.org/10.1007/s00253-010-2676-2
    • (2010) Appl Microbiol Biotechnol , vol.87 , pp. 2001-2009
    • Li, Z.J.1    Jian, J.2    Wei, X.X.3    Shen, X.W.4    Chen, G.Q.5
  • 16
    • 71549166006 scopus 로고    scopus 로고
    • Structural basis for chiral substrate recognition by two 2,3-butanediol dehydrogenases
    • Otagiri M, Ui S, Takusagawa Y, Ohtsuki T, Kurisu G, Kusunoki M. 2010. Structural basis for chiral substrate recognition by two 2,3-butanediol dehydrogenases. FEBS Lett 584:219-223. http://dx.doi.org/10.1016/j.febslet.2009.11.068
    • (2010) FEBS Lett , vol.584 , pp. 219-223
    • Otagiri, M.1    Ui, S.2    Takusagawa, Y.3    Ohtsuki, T.4    Kurisu, G.5    Kusunoki, M.6
  • 17
    • 5744238410 scopus 로고    scopus 로고
    • Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions
    • Kaluzna IA, Matsuda T, Sewell AK, Stewart JD. 2004. Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions. J Am Chem Soc 126:12827-12832. http://dx.doi.org/10.1021/ja0469479
    • (2004) J Am Chem Soc , vol.126 , pp. 12827-12832
    • Kaluzna, I.A.1    Matsuda, T.2    Sewell, A.K.3    Stewart, J.D.4
  • 18
    • 77749245897 scopus 로고    scopus 로고
    • A novel whole-cell biocatalyst with NAD+ regeneration for production of chiral chemicals
    • Xiao Z, Lv C, Gao C, Qin J, Ma C, Liu Z, Liu P, Li L, Xu P. 2010. A novel whole-cell biocatalyst with NAD+ regeneration for production of chiral chemicals. PLoS One 5:e8860. http://dx.doi.org/10.1371/journal.pone.0008860
    • (2010) PLoS One , vol.5
    • Xiao, Z.1    Lv, C.2    Gao, C.3    Qin, J.4    Ma, C.5    Liu, Z.6    Liu, P.7    Li, L.8    Xu, P.9
  • 19
    • 0034680769 scopus 로고    scopus 로고
    • Characterization of a (2R,3R)-2,3-butanediol dehydrogenase as the Saccharomyces cerevisiae YAL060W gene product. Disruption and induction of the gene
    • González E, Fernández MR, Larroy C, Solá L, Pericás MA, Parés X, Biosca JA. 2000. Characterization of a (2R,3R)-2,3-butanediol dehydrogenase as the Saccharomyces cerevisiae YAL060W gene product. Disruption and induction of the gene. J Biol Chem 275:35876-35885
    • (2000) J Biol Chem , vol.275 , pp. 35876-35885
    • González, E.1    Fernández, M.R.2    Larroy, C.3    Solá, L.4    Pericás, M.A.5    Parés, X.6    Biosca, J.A.7
  • 20
    • 75749132831 scopus 로고    scopus 로고
    • Role of Saccharomyces cerevisiae oxidoreductases Bdh1p and Ara1p in the metabolism of acetoin and 2,3-butanediol
    • González E, Fernández MR, Marco D, Calam E, Sumoy L, Parés X, Dequin S, Biosca JA. 2010. Role of Saccharomyces cerevisiae oxidoreductases Bdh1p and Ara1p in the metabolism of acetoin and 2,3-butanediol. Appl Environ Microbiol 76:670-679. http://dx.doi.org/10.1128/AEM.01521-09
    • (2010) Appl Environ Microbiol , vol.76 , pp. 670-679
    • González, E.1    Fernández, M.R.2    Marco, D.3    Calam, E.4    Sumoy, L.5    Parés, X.6    Dequin, S.7    Biosca, J.A.8
  • 21
    • 0034903337 scopus 로고    scopus 로고
    • In vivo site-directed mutagenesis using oligonucleotides
    • Storici F, Lewis LK, Resnick MA. 2001. In vivo site-directed mutagenesis using oligonucleotides. Nat Biotechnol 19:773-776. http://dx.doi.org/10.1038/90837
    • (2001) Nat Biotechnol , vol.19 , pp. 773-776
    • Storici, F.1    Lewis, L.K.2    Resnick, M.A.3
  • 22
    • 0028794516 scopus 로고
    • Construction of a set of convenient Saccharomyces cerevisiae strains that are isogenic to S288C
    • Winston F, Dollard C, Ricupero-Hovasse SL. 1995. Construction of a set of convenient Saccharomyces cerevisiae strains that are isogenic to S288C. Yeast 11:53-55. http://dx.doi.org/10.1002/yea.320110107
    • (1995) Yeast , vol.11 , pp. 53-55
    • Winston, F.1    Dollard, C.2    Ricupero-Hovasse, S.L.3
  • 23
    • 0020529962 scopus 로고
    • Transformation of intact yeast cells treated with alkali cations
    • Ito H, Fukuda Y, Murata K, Kimura A. 1983. Transformation of intact yeast cells treated with alkali cations. J Bacteriol 153:163-168
    • (1983) J Bacteriol , vol.153 , pp. 163-168
    • Ito, H.1    Fukuda, Y.2    Murata, K.3    Kimura, A.4
  • 24
    • 0028676232 scopus 로고
    • New heterologous modules for classical or PCR-based gene disruptions in Saccharomyces cerevisiae
    • Wach A, Brachat A, Pöhlmann R, Philippsen P. 1994. New heterologous modules for classical or PCR-based gene disruptions in Saccharomyces cerevisiae. Yeast 10:1793-1808. http://dx.doi.org/10.1002/yea.320101310
    • (1994) Yeast , vol.10 , pp. 1793-1808
    • Wach, A.1    Brachat, A.2    Pöhlmann, R.3    Philippsen, P.4
  • 25
    • 0032873415 scopus 로고    scopus 로고
    • Three new dominant drug resistance cassettes for gene disruption in Saccharomyces cerevisiae
    • Goldstein AL, McCusker JH. 1999. Three new dominant drug resistance cassettes for gene disruption in Saccharomyces cerevisiae. Yeast 15:1541-1553
    • (1999) Yeast , vol.15 , pp. 1541-1553
    • Goldstein, A.L.1    McCusker, J.H.2
  • 27
    • 0023484186 scopus 로고
    • 5-Fluoroorotic acid as a selective agent in yeast molecular genetics
    • Boeke JD, Trueheart J, Natsoulis G, Fink GR. 1987. 5-Fluoroorotic acid as a selective agent in yeast molecular genetics. Methods Enzymol 154: 164-175. http://dx.doi.org/10.1016/0076-6879(87)54076-9
    • (1987) Methods Enzymol , vol.154 , pp. 164-175
    • Boeke, J.D.1    Trueheart, J.2    Natsoulis, G.3    Fink, G.R.4
  • 28
    • 0029125658 scopus 로고
    • Digitonin permeabilization of Saccharomyces cerevisiae cells for in situ enzyme assay
    • Cordeiro C, Freire AP. 1995. Digitonin permeabilization of Saccharomyces cerevisiae cells for in situ enzyme assay. Anal Biochem 229:145-148. http://dx.doi.org/10.1006/abio.1995.1394
    • (1995) Anal Biochem , vol.229 , pp. 145-148
    • Cordeiro, C.1    Freire, A.P.2
  • 29
    • 46849086039 scopus 로고    scopus 로고
    • Regeneration of cofactors in enzyme biocatalysis
    • Pandey A, Webb C, Soccol CR, Laroche C (ed), Springer Science, New Delhi, India
    • Woodyer RD, Johannes TW, Zhao H. 2006. Regeneration of cofactors in enzyme biocatalysis, p 83-100. In Pandey A, Webb C, Soccol CR, Laroche C (ed), Enzyme technology. Springer Science, New Delhi, India
    • (2006) Enzyme technology , pp. 83-100
    • Woodyer, R.D.1    Johannes, T.W.2    Zhao, H.3
  • 30
    • 0030792275 scopus 로고    scopus 로고
    • Modulation of glycerol and ethanol yields during alcoholic fermentation in Saccharomyces cerevisiae strains overexpressed or disrupted for GPD1 encoding glycerol 3-phosphate dehydrogenase
    • Michnick S, Roustan JL, Remize F, Barre P, Dequin S. 1997. Modulation of glycerol and ethanol yields during alcoholic fermentation in Saccharomyces cerevisiae strains overexpressed or disrupted for GPD1 encoding glycerol 3-phosphate dehydrogenase. Yeast 13:783-793. http://dx.doi.org/10.1002/(SICI)1097-0061(199707)13:9<783::AID-YEA128>3.0.CO;2-W
    • (1997) Yeast , vol.13 , pp. 783-793
    • Michnick, S.1    Roustan, J.L.2    Remize, F.3    Barre, P.4    Dequin, S.5
  • 31
    • 84985727190 scopus 로고
    • Regio-, diastereo-, and enantioselective synthesis of vic-diols via α-silyl ketones according to the SAMP/RAMP hydrazone method
    • Enders D, Nakai S. 1991. Regio-, diastereo-, and enantioselective synthesis of vic-diols via α-silyl ketones according to the SAMP/RAMP hydrazone method. Chem Ber 124:219-226. http://dx.doi.org/10.1002/cber.19911240133
    • (1991) Chem Ber , vol.124 , pp. 219-226
    • Enders, D.1    Nakai, S.2
  • 32
    • 21844456512 scopus 로고    scopus 로고
    • Off-flavours in water: hydroxyketones and β-ionone derivatives as new odour compounds of freshwater cyanobacteria
    • Höckelmann C, Jüttner F. 2005. Off-flavours in water: hydroxyketones and β-ionone derivatives as new odour compounds of freshwater cyanobacteria. Flavour Fragr J 20:387-394. http://dx.doi.org/10.1002/ffj.1464
    • (2005) Flavour Fragr J , vol.20 , pp. 387-394
    • Höckelmann, C.1    Jüttner, F.2
  • 33
    • 84875219190 scopus 로고    scopus 로고
    • Biocatalytic production of alpha-hydroxy ketones and vicinal diols by yeast and human aldo-keto reductases
    • Calam E, Porté S, Fernández MR, Farrés J, Parés X, Biosca JA. 2013. Biocatalytic production of alpha-hydroxy ketones and vicinal diols by yeast and human aldo-keto reductases. Chem Biol Interact 202:195-203. http://dx.doi.org/10.1016/j.cbi.2012.12.006
    • (2013) Chem Biol Interact , vol.202 , pp. 195-203
    • Calam, E.1    Porté, S.2    Fernández, M.R.3    Farrés, J.4    Parés, X.5    Biosca, J.A.6
  • 34
    • 84988073706 scopus 로고
    • Synthesis of (3R)-3-hydroxy-2-hexanone, (2R,3R)-2,3-hexanediol and (2S,3R)-2,3-hexanediol, the male sex pheromone of Hylotrupes bajulus and Pyrrhidium sanguineum (Cerambycidae)
    • Schröder F, Fettköther R, Noldt U, Dettner K, Knïg WA, Francke W. 1994. Synthesis of (3R)-3-hydroxy-2-hexanone, (2R,3R)-2,3-hexanediol and (2S,3R)-2,3-hexanediol, the male sex pheromone of Hylotrupes bajulus and Pyrrhidium sanguineum (Cerambycidae). Liebigs Ann Chem 1994:1211-1218
    • (1994) Liebigs Ann Chem , vol.1994 , pp. 1211-1218
    • Schröder, F.1    Fettköther, R.2    Noldt, U.3    Dettner, K.4    Knïg, W.A.5    Francke, W.6
  • 35
    • 0036845955 scopus 로고    scopus 로고
    • Engineering of coenzyme specificity of formate dehydrogenase from Saccharomyces cerevisiae
    • Serov AE, Popova AS, Fedorchuk VV, Tishkov VI. 2002. Engineering of coenzyme specificity of formate dehydrogenase from Saccharomyces cerevisiae. Biochem J 367:841-847. http://dx.doi.org/10.1042/bj20020379
    • (2002) Biochem J , vol.367 , pp. 841-847
    • Serov, A.E.1    Popova, A.S.2    Fedorchuk, V.V.3    Tishkov, V.I.4
  • 36
    • 34249807630 scopus 로고    scopus 로고
    • High-resolution structures of formate dehydrogenase from Candida boidinii
    • Schirwitz K, Schmidt A, Lamzin VS. 2007. High-resolution structures of formate dehydrogenase from Candida boidinii. Protein Sci 16:1146-1156. http://dx.doi.org/10.1110/ps.062741707
    • (2007) Protein Sci , vol.16 , pp. 1146-1156
    • Schirwitz, K.1    Schmidt, A.2    Lamzin, V.S.3
  • 37
    • 77956368203 scopus 로고    scopus 로고
    • Enantioselective reduction of prochiral ketones by engineered bifunctional fusion proteins
    • Hölsch K, Weuster-Botz D. 2010. Enantioselective reduction of prochiral ketones by engineered bifunctional fusion proteins. Biotechnol Appl Biochem 56:131-140. http://dx.doi.org/10.1042/BA20100143
    • (2010) Biotechnol Appl Biochem , vol.56 , pp. 131-140
    • Hölsch, K.1    Weuster-Botz, D.2
  • 38
    • 84885445388 scopus 로고    scopus 로고
    • Crystallization and preliminary X-ray study of a (2R,3R)-2,3-butanediol dehydrogenase from Bacillus coagulans 2-6
    • Miao X, Huang X, Zhang G, Zhao X, Zhu X, Dong H. 2013. Crystallization and preliminary X-ray study of a (2R,3R)-2,3-butanediol dehydrogenase from Bacillus coagulans 2-6. Acta Crystallogr Sect F Struct Biol Cryst Commun 69:1140-1142. http://dx.doi.org/10.1107/S174430911302410X
    • (2013) Acta Crystallogr Sect F Struct Biol Cryst Commun , vol.69 , pp. 1140-1142
    • Miao, X.1    Huang, X.2    Zhang, G.3    Zhao, X.4    Zhu, X.5    Dong, H.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.