메뉴 건너뛰기




Volumn 17, Issue 2, 2013, Pages 293-300

Squalene hopene cyclases: Highly promiscuous and evolvable catalysts for stereoselective CC and CX bond formation

Author keywords

[No Author keywords available]

Indexed keywords

ISOPRENE; NUCLEOPHILE; SQUALENE; TERPENE;

EID: 84876731984     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2013.01.016     Document Type: Review
Times cited : (57)

References (48)
  • 2
  • 4
    • 70349515856 scopus 로고    scopus 로고
    • C2-Ketol elongation by transketolase-catalyzed asymmetric synthesis
    • Wohlgemuth R. C2-Ketol elongation by transketolase-catalyzed asymmetric synthesis. J Mol Catal B Enzym 2009, 61:23-29.
    • (2009) J Mol Catal B Enzym , vol.61 , pp. 23-29
    • Wohlgemuth, R.1
  • 5
    • 65949118468 scopus 로고    scopus 로고
    • Enantioselective enzyme-catalysed synthesis of cyanohydrins
    • Holt J., Hanefeld U. Enantioselective enzyme-catalysed synthesis of cyanohydrins. Curr Org Synth 2009, 6:15-37.
    • (2009) Curr Org Synth , vol.6 , pp. 15-37
    • Holt, J.1    Hanefeld, U.2
  • 6
    • 65549162613 scopus 로고    scopus 로고
    • Thiamin diphosphate in biological chemistry: exploitation of diverse thiamin diphosphate-dependent enzymes for asymmetric chemoenzymatic synthesis
    • Müller M., Gocke D., Pohl M. Thiamin diphosphate in biological chemistry: exploitation of diverse thiamin diphosphate-dependent enzymes for asymmetric chemoenzymatic synthesis. FEBS J 2009, 276:2894-2904.
    • (2009) FEBS J , vol.276 , pp. 2894-2904
    • Müller, M.1    Gocke, D.2    Pohl, M.3
  • 8
    • 21244452391 scopus 로고    scopus 로고
    • Enzyme mechanisms for triterpene cyclization: new pieces of the puzzle
    • Wendt K.U. Enzyme mechanisms for triterpene cyclization: new pieces of the puzzle. Angew Chem Int Ed 2005, 44:3966-3971.
    • (2005) Angew Chem Int Ed , vol.44 , pp. 3966-3971
    • Wendt, K.U.1
  • 9
    • 33947468722 scopus 로고
    • The stereochemistry of polyene cyclization
    • BA W.
    • Stork G., BA W. The stereochemistry of polyene cyclization. J Am Chem Soc 1955, 77:5068-5077.
    • (1955) J Am Chem Soc , vol.77 , pp. 5068-5077
    • Stork, G.1
  • 10
    • 33745683617 scopus 로고    scopus 로고
    • Recent progress in chiral Brønsted acid catalysis
    • Akiyama T., Itoh J., Fuchibe K. Recent progress in chiral Brønsted acid catalysis. Adv Synth Catal 2006, 348:999-1010.
    • (2006) Adv Synth Catal , vol.348 , pp. 999-1010
    • Akiyama, T.1    Itoh, J.2    Fuchibe, K.3
  • 11
    • 77950248809 scopus 로고    scopus 로고
    • Chiral Brønsted acids for asymmetric organocatalysis
    • Kampen D., Reisinger C.M., List B. Chiral Brønsted acids for asymmetric organocatalysis. Top Curr Chem 2010, 291:395-456.
    • (2010) Top Curr Chem , vol.291 , pp. 395-456
    • Kampen, D.1    Reisinger, C.M.2    List, B.3
  • 12
    • 1142281936 scopus 로고    scopus 로고
    • Conversion of squalene to the pentacarbocyclic hopene
    • Reinert D.J., Balliano G., Schulz G.E. Conversion of squalene to the pentacarbocyclic hopene. Chem Biol 2004, 11:121-126.
    • (2004) Chem Biol , vol.11 , pp. 121-126
    • Reinert, D.J.1    Balliano, G.2    Schulz, G.E.3
  • 13
    • 84863784511 scopus 로고    scopus 로고
    • The triterpene cyclase protein family: a systematic analysis
    • Racolta S., Juhl P.B., Sirim D., Pleiss J. The triterpene cyclase protein family: a systematic analysis. Proteins 2012, 80:2009-2019.
    • (2012) Proteins , vol.80 , pp. 2009-2019
    • Racolta, S.1    Juhl, P.B.2    Sirim, D.3    Pleiss, J.4
  • 14
    • 65349154505 scopus 로고    scopus 로고
    • Phylogenetic analysis of the triterpene cyclase protein family in prokaryotes and eukaryotes suggests bidirectional lateral gene transfer
    • Frickey T., Kannenberg E.L. Phylogenetic analysis of the triterpene cyclase protein family in prokaryotes and eukaryotes suggests bidirectional lateral gene transfer. Environ Microbiol 2009, 11:1224-1241.
    • (2009) Environ Microbiol , vol.11 , pp. 1224-1241
    • Frickey, T.1    Kannenberg, E.L.2
  • 15
    • 84871576542 scopus 로고    scopus 로고
    • Terpenoid synthase structures: a so far incomplete view of complex catalysis
    • Gao Y., Honzatko R.B., Peters R.J. Terpenoid synthase structures: a so far incomplete view of complex catalysis. Nat Prod Rep 2012, 29:1153-1175.
    • (2012) Nat Prod Rep , vol.29 , pp. 1153-1175
    • Gao, Y.1    Honzatko, R.B.2    Peters, R.J.3
  • 16
    • 0031891866 scopus 로고    scopus 로고
    • Sesquiterpene synthases from grand fir (Abies grandis)
    • Steele C.L., Crock J., Bohlmann J., Croteau R.B. Sesquiterpene synthases from grand fir (Abies grandis). J Biol Chem 1998, 273:2078-2089.
    • (1998) J Biol Chem , vol.273 , pp. 2078-2089
    • Steele, C.L.1    Crock, J.2    Bohlmann, J.3    Croteau, R.B.4
  • 17
    • 33646145081 scopus 로고    scopus 로고
    • Biosynthetic potential of sesquiterpene synthases: alternative products of tobacco 5-epi-aristolochene synthase
    • O'Maille P.E., Chappell J., Noel J.P. Biosynthetic potential of sesquiterpene synthases: alternative products of tobacco 5-epi-aristolochene synthase. Arch Biochem Biophys 2006, 448:73-82.
    • (2006) Arch Biochem Biophys , vol.448 , pp. 73-82
    • O'Maille, P.E.1    Chappell, J.2    Noel, J.P.3
  • 18
    • 34548757971 scopus 로고    scopus 로고
    • An oxidosqualene cyclase makes numerous products by diverse mechanisms: a challenge to prevailing concepts of triterpene biosynthesis
    • Lodeiro S., Xiong Q., Wilson W.K., Kolesnikova M.D., Onak C.S., Matsuda S.P.T. An oxidosqualene cyclase makes numerous products by diverse mechanisms: a challenge to prevailing concepts of triterpene biosynthesis. J Am Chem Soc 2007, 129:11213-11222.
    • (2007) J Am Chem Soc , vol.129 , pp. 11213-11222
    • Lodeiro, S.1    Xiong, Q.2    Wilson, W.K.3    Kolesnikova, M.D.4    Onak, C.S.5    Matsuda, S.P.T.6
  • 20
    • 43049107992 scopus 로고    scopus 로고
    • Unearthing the roots of the terpenome
    • Christianson D.W. Unearthing the roots of the terpenome. Curr Opin Chem Biol 2008, 12:141-150.
    • (2008) Curr Opin Chem Biol , vol.12 , pp. 141-150
    • Christianson, D.W.1
  • 21
    • 77952129776 scopus 로고    scopus 로고
    • Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers
    • Lopez-Gallego F., Agger S.A., Abate-Pella D., Distefano M.D., Schmidt-Dannert C. Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers. Chembiochem 2010, 11:1093-1106.
    • (2010) Chembiochem , vol.11 , pp. 1093-1106
    • Lopez-Gallego, F.1    Agger, S.A.2    Abate-Pella, D.3    Distefano, M.D.4    Schmidt-Dannert, C.5
  • 22
    • 19744366357 scopus 로고    scopus 로고
    • Taxadiene synthase-catalyzed cyclization of 6-fluorogeranylgeranyl diphosphate to 7-fluoroverticillenes
    • Jin Y., Williams D.C., Croteau R.B., Coates R.M. Taxadiene synthase-catalyzed cyclization of 6-fluorogeranylgeranyl diphosphate to 7-fluoroverticillenes. J Am Chem Soc 2005, 127:7834-7842.
    • (2005) J Am Chem Soc , vol.127 , pp. 7834-7842
    • Jin, Y.1    Williams, D.C.2    Croteau, R.B.3    Coates, R.M.4
  • 23
    • 37549036742 scopus 로고    scopus 로고
    • A single residue switch converts abietadiene synthase into a pimaradiene specific cyclase
    • Wilderman P.R., Peters R.J. A single residue switch converts abietadiene synthase into a pimaradiene specific cyclase. J Am Chem Soc 2007, 129:15736-15737.
    • (2007) J Am Chem Soc , vol.129 , pp. 15736-15737
    • Wilderman, P.R.1    Peters, R.J.2
  • 24
    • 33745631233 scopus 로고    scopus 로고
    • Identifying and manipulating structural determinates linking catalytic specificities in terpene synthases
    • Greenhagen B.T., O'Maille P.E., Noel J.P., Chappell J. Identifying and manipulating structural determinates linking catalytic specificities in terpene synthases. Proc Natl Acad Sci USA 2006, 103:9826-9831.
    • (2006) Proc Natl Acad Sci USA , vol.103 , pp. 9826-9831
    • Greenhagen, B.T.1    O'Maille, P.E.2    Noel, J.P.3    Chappell, J.4
  • 25
    • 33646178621 scopus 로고    scopus 로고
    • Designed divergent evolution of enzyme function
    • Yoshikuni Y., Ferrin T.E., Keasling J.D. Designed divergent evolution of enzyme function. Nature 2006, 440:1078-1082.
    • (2006) Nature , vol.440 , pp. 1078-1082
    • Yoshikuni, Y.1    Ferrin, T.E.2    Keasling, J.D.3
  • 29
    • 80455168097 scopus 로고    scopus 로고
    • Bifunctional Triterpene/Sesquarterpene Cyclase Tetraprenyl-β-curcumene cyclase is also squalene cyclase in Bacillus megaterium
    • Sato T., Hoshino H., Yoshida S., Nakajima M., Hoshino T. Bifunctional Triterpene/Sesquarterpene Cyclase Tetraprenyl-β-curcumene cyclase is also squalene cyclase in Bacillus megaterium. J Am Chem Soc 2011, 133:17540-17543.
    • (2011) J Am Chem Soc , vol.133 , pp. 17540-17543
    • Sato, T.1    Hoshino, H.2    Yoshida, S.3    Nakajima, M.4    Hoshino, T.5
  • 31
    • 79959374838 scopus 로고    scopus 로고
    • Structure and mechanism of the diterpene cyclase ent-copalyl diphosphate synthase
    • Köksal M., Hu H., Coates R.M., Peters R.J., Christianson D.W. Structure and mechanism of the diterpene cyclase ent-copalyl diphosphate synthase. Nat Chem Biol 2011, 7:431-433.
    • (2011) Nat Chem Biol , vol.7 , pp. 431-433
    • Köksal, M.1    Hu, H.2    Coates, R.M.3    Peters, R.J.4    Christianson, D.W.5
  • 32
    • 33644854595 scopus 로고    scopus 로고
    • Structure and mechanism of the lantibiotic cyclase involved in nisin biosynthesis
    • Li B., Yu J.P.J., Brunzelle J.S., Moll G.N., van der Donk W.A., Nair S.K. Structure and mechanism of the lantibiotic cyclase involved in nisin biosynthesis. Science 2006, 311:1464-1467.
    • (2006) Science , vol.311 , pp. 1464-1467
    • Li, B.1    Yu, J.P.J.2    Brunzelle, J.S.3    Moll, G.N.4    van der Donk, W.A.5    Nair, S.K.6
  • 33
    • 0022761844 scopus 로고
    • Purification, partial characterization and substrate specificity of a squalene cyclase from Bacillus acidocaldarius
    • Neumann S., Simon H. Purification, partial characterization and substrate specificity of a squalene cyclase from Bacillus acidocaldarius. Biol Chem Hoppe-Seyler 1986, 367:723-729.
    • (1986) Biol Chem Hoppe-Seyler , vol.367 , pp. 723-729
    • Neumann, S.1    Simon, H.2
  • 35
    • 0037065291 scopus 로고    scopus 로고
    • Enzymatic formation of an unnatural hexacyclic C35 polyprenoid by bacterial squalene cyclase
    • Abe I., Tanaka H., Noguchi H. Enzymatic formation of an unnatural hexacyclic C35 polyprenoid by bacterial squalene cyclase. J Am Chem Soc 2002, 124:14514-14515.
    • (2002) J Am Chem Soc , vol.124 , pp. 14514-14515
    • Abe, I.1    Tanaka, H.2    Noguchi, H.3
  • 36
    • 60749124172 scopus 로고    scopus 로고
    • Reviewing the polyolefin cyclization reaction of the C 35 polyprene
    • Hoshino T., Kumai Y., Sato T. Reviewing the polyolefin cyclization reaction of the C 35 polyprene. Chem Eur J 2009, 15:2091-2100.
    • (2009) Chem Eur J , vol.15 , pp. 2091-2100
    • Hoshino, T.1    Kumai, Y.2    Sato, T.3
  • 37
    • 84864455295 scopus 로고    scopus 로고
    • Chemo-enzymatic syntheses of drimane-type sesquiterpenes and the fundamental core of hongoquercin meroterpenoid by recombinant squalene-hopene cyclase
    • Yonemura Y., Ohyama T., Hoshino T. Chemo-enzymatic syntheses of drimane-type sesquiterpenes and the fundamental core of hongoquercin meroterpenoid by recombinant squalene-hopene cyclase. Org Biomol Chem 2011, 4:3-9.
    • (2011) Org Biomol Chem , vol.4 , pp. 3-9
    • Yonemura, Y.1    Ohyama, T.2    Hoshino, T.3
  • 38
    • 80051743897 scopus 로고    scopus 로고
    • Isolation, chemical and biotransformation routes of labdane-type diterpenes
    • Frija L.M.T., Frade R.F.M., Afonso C.A.M. Isolation, chemical and biotransformation routes of labdane-type diterpenes. Chem Rev 2011, 111:4418-4452.
    • (2011) Chem Rev , vol.111 , pp. 4418-4452
    • Frija, L.M.T.1    Frade, R.F.M.2    Afonso, C.A.M.3
  • 40
    • 0037463518 scopus 로고    scopus 로고
    • First formal synthesis of (+)-nimbidiol. Synthesis, X-ray structure and anticancer activity of a novel ring C aromatic diterpene: dimethyl(+)-podocarpa-8,11,13-triene-12,13-dicarboxylate
    • Zambrano J.L., Rosales V., Nakano T. First formal synthesis of (+)-nimbidiol. Synthesis, X-ray structure and anticancer activity of a novel ring C aromatic diterpene: dimethyl(+)-podocarpa-8,11,13-triene-12,13-dicarboxylate. Tetrahedron Lett 2003, 44:1859-1862.
    • (2003) Tetrahedron Lett , vol.44 , pp. 1859-1862
    • Zambrano, J.L.1    Rosales, V.2    Nakano, T.3
  • 41
    • 68249113421 scopus 로고    scopus 로고
    • Meroterpenoids produced by fungi
    • Geris R., Simpson T.J. Meroterpenoids produced by fungi. Nat Prod Rep 2009, 26:1063-1094.
    • (2009) Nat Prod Rep , vol.26 , pp. 1063-1094
    • Geris, R.1    Simpson, T.J.2
  • 42
    • 80051716582 scopus 로고    scopus 로고
    • Asymmetric organocatalytic cyclization and cycloaddition reactions
    • Moyano A., Rios R. Asymmetric organocatalytic cyclization and cycloaddition reactions. Chem Rev 2011, 111:4703-4832.
    • (2011) Chem Rev , vol.111 , pp. 4703-4832
    • Moyano, A.1    Rios, R.2
  • 44
    • 84864432284 scopus 로고    scopus 로고
    • Stereoselective Friedel-Crafts alkylation catalyzed by squalene hopene cyclases
    • Hammer S.C., Dominicus J.M., Syrén P.-O., Nestl B.M., Hauer B. Stereoselective Friedel-Crafts alkylation catalyzed by squalene hopene cyclases. Tetrahedron 2012, 68:7624-7629.
    • (2012) Tetrahedron , vol.68 , pp. 7624-7629
    • Hammer, S.C.1    Dominicus, J.M.2    Syrén, P.-O.3    Nestl, B.M.4    Hauer, B.5
  • 45
    • 84939950162 scopus 로고    scopus 로고
    • Biocatalytic production of Ambroxan
    • WO2010/139719 2010
    • Breuer M, Hörster A, Hauer B: Biocatalytic production of Ambroxan. WO2010/139719 2010, 1-36.
    • Breuer, M.1    Hörster, A.2    Hauer, B.3
  • 46
    • 2942687466 scopus 로고    scopus 로고
    • Squalene-hopene cyclase: final deprotonation reaction, conformational analysis for the cyclization of (3R,S)-2,3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the E-ring
    • Hoshino T., Nakano S., Kondo T., Sato T., Miyoshi A. Squalene-hopene cyclase: final deprotonation reaction, conformational analysis for the cyclization of (3R,S)-2,3-oxidosqualene and further evidence for the requirement of an isopropylidene moiety both for initiation of the polycyclization cascade and for the formation of the E-ring. Org Biomol Chem 2004, 2:1456-1470.
    • (2004) Org Biomol Chem , vol.2 , pp. 1456-1470
    • Hoshino, T.1    Nakano, S.2    Kondo, T.3    Sato, T.4    Miyoshi, A.5
  • 48
    • 84874359209 scopus 로고    scopus 로고
    • Prokaryotic squalene-hopene cyclases can be converted to citronellal cyclases by single amino acid exchange
    • Siedenburg G., Breuer M., Jendrossek D Prokaryotic squalene-hopene cyclases can be converted to citronellal cyclases by single amino acid exchange. Appl Microbiol Biotechnol 2013, 97:1571-1580.
    • (2013) Appl Microbiol Biotechnol , vol.97 , pp. 1571-1580
    • Siedenburg, G.1    Breuer, M.2    Jendrossek, D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.