Reference on EC 5.4.99.17 - squalene-hopene cyclase
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REF. 
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ceruti, M.; Balliano, G.; Rocco, F.; Milla, P.; Arpicco, S.; Cattel, L.; Viola, F.
Vinyl sulfide derivatives of truncated oxidosqualene as selective inhibitors of oxidosqualene and squalene-hopene cyclases
Lipids
36
629-636
2001
Alicyclobacillus acidocaldarius
Dang, T.; Prestwich, G.D.
Site-directed mutagenesis of squalene-hopene cyclase: altered substrate specificity and product distribution
Chem. Biol.
7
643-649
2000
Alicyclobacillus acidocaldarius
Douka, E.; Koukkou, A.; Drainas, C.; Grosdemange-Billiard, C.; Rohmer, M.
Structural diversity of the triterpenic hydrocarbons from the bacterium Zymomonas mobilis: the signature of defective squalene cyclization by the squalene/hopene cyclase
FEMS Microbiol. Lett.
199
247-251
2001
Zymomonas mobilis
Feil, C.; Suessmuth, R.; Jung, G.; Poralla, K.
Site-directed mutagenesis of putative active-site residues in squalene-hopene cyclase
Eur. J. Biochem.
242
51-55
1996
Alicyclobacillus acidocaldarius
Full, C.
Bicyclic triterpenes as new main products of squalene-hopene cyclase by mutation at conserved tyrosine residues
FEBS Lett.
509
361-364
2001
Alicyclobacillus acidocaldarius
Full, C.; Poralla, K.
Conserved Tyr residues determine functions of Alicyclobacillus acidocaldarius squalene-hopene cyclase
FEMS Microbiol. Lett.
183
221-224
2000
Alicyclobacillus acidocaldarius
Hoshino, T.; Kouda, M.; Abe, T.; Sato, T.
Functional analysis of Phe605, a conserved aromatic amino acid in squalene-hopene cyclases
Chem. Commun. (Camb.)
2000
1485-1486
2000
Alicyclobacillus acidocaldarius
-
Hoshino, T.; Sato, T.
Squalene-hopene cyclase: catalytic mechanism and substrate recognition
Chem. Commun. (Camb.)
2000
291-301
2002
Alicyclobacillus acidocaldarius
-
Kleemann, G.; Kellner, R.; Poralla, K.
Purification and properties of the squalene-hopene cyclase from Rhodopseudomonas palustris, a purple non-sulfur bacterium producing hopanoids and tetrahymanol
Biochim. Biophys. Acta
1210
317-320
1994
Rhodopseudomonas palustris
Milla, P.; Lenhart, A.; Grosa, G.; Viola, F.; Weihofen, W.A.; Schulz, G.E.; Balliano, G.
Thiol-modifying inhibitors for understanding squalene cyclase function
Eur. J. Biochem.
269
2108-2116
2002
Alicyclobacillus acidocaldarius
Ochs, D.; Tappe, C.H.; Gaertner, P.; Kellner, R.; Poralla, K.
Properties of purified squalene-hopene cyclase from Bacillus acidocaldarius
Eur. J. Biochem.
194
75-80
1990
Alicyclobacillus acidocaldarius
Sato, T.; Hoshino, T.
Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site-directed mutagenesis experiments: initiation site of the polycyclization reaction and stabilization site of the carbocation intermediate of the initially cyclized A-ring
Biosci. Biotechnol. Biochem.
63
2189-2198
1999
Alicyclobacillus acidocaldarius
Sato, T.; Hoshino, T.
Kinetic studies on the function of all the conserved tryptophans involved inside and outside the QW motifs of squalene-hopene cyclase: stabilizing effect of the protein structure against thermal denaturation
Biosci. Biotechnol. Biochem.
63
1171-1180
1999
Alicyclobacillus acidocaldarius
Sato, T.; Sasahara, S.; Yamakami, T.; Hoshino, T.
Functional analyses of Tyr420 and Leu607 of Alicyclobacillus acidocaldarius squalene-hopene cyclase. Neoachillapentaene, a novel triterpene with the 1,5,6-trimethylcyclohexene moiety produced through folding of the constrained boat structure
Biosci. Biotechnol. Biochem.
66
1660-1670
2002
Alicyclobacillus acidocaldarius
Schmidt, A.; Bringer-Meyer, S.; Poralla, K.; Sahm, H.
Influence of ethanol on the activities of 3-hydroxy-3-methylglutaryl-coenzyme A-reductase and squalene-hopene-cyclase in Zymomonas mobilis
Appl. Microbiol. Biotechnol.
30
170-175
1989
Zymomonas mobilis
-
Seckler, B.; Poralla, K.
Characterization and partial purification of squalene-hopene cyclase from Bacillus acidocaldarius
Biochim. Biophys. Acta
881
356-363
1986
Alicyclobacillus acidocaldarius, Alicyclobacillus acidocaldarius 104-IA
-
Tippelt, A.; Jahnke, L.; Poralla, K.
Squalene-hopene cyclase from Methylococcus capsulatus (Bath): a bacterium producing hopanoids and steroids
Biochim. Biophys. Acta
1391
223-232
1998
Methylococcus capsulatus, Methylococcus capsulatus Bath
Wendt, K.U.; Lenhart, A.; Schulz, G.E.
The structure of the membrane protein squalene-hopene cyclase at 2.0.ANG. resolution
J. Mol. Biol.
286
175-187
1999
Alicyclobacillus acidocaldarius (P33247), Alicyclobacillus acidocaldarius
Zheng, Y.F.; Abe, I.; Prestwich, G.D.
Inhibition kinetics and affinity labeling of bacterial squalene:hopene cyclase by thia-substituted analogs of 2,3-oxidosqualene
Biochemistry
37
5981-5987
1998
Alicyclobacillus acidocaldarius
Sato, T.; Kouda, M.; Hoshino, T.
Site-directed mutagenesis experiments on the putative deprotonation site of squalene-hopene cyclase from Alicyclobacillus acidocaldarius
Biosci. Biotechnol. Biochem.
68
728-738
2004
Alicyclobacillus acidocaldarius
Reinert, D.J.; Balliano, G.; Schulz, G.E.
Conversion of squalene to the pentacarbocyclic hopene
Chem. Biol.
11
121-126
2004
Alicyclobacillus acidocaldarius
Cravotto, G.; Balliano, G.; Tagliapietra, S.; Palmisano, G.; Penoni, A.
Umbelliferone aminoalkyl derivatives, a new class of squalene-hopene cyclase inhibitors
Eur. J. Med. Chem.
39
917-924
2004
Alicyclobacillus acidocaldarius
Lenhart, A.; Reinert, D.J.; Aebi, J.D.; Dehmlow, H.; Morand, O.H.; Schulz, G.E.
Binding structures and potencies of oxidosqualene cyclase inhibitors with the homologous squalene-hopene cyclase
J. Med. Chem.
46
2083-2092
2003
Alicyclobacillus acidocaldarius (P33247), Alicyclobacillus acidocaldarius
Rocco, F.; Bosso, S.O.; Viola, F.; Milla, P.; Roma, G.; Grossi, G.; Ceruti, M.
Conjugated methyl sulfide and phenyl sulfide derivatives of oxidosqualene as inhibitors of oxidosqualene and squalene-hopene cyclases
Lipids
38
201-207
2003
Alicyclobacillus acidocaldarius
Ceruti, M.; Balliano, G.; Rocco, F.; Lenhart, A.; Schulz, G.E.; Castelli, F.; Milla, P.
Synthesis and biological activity of new iodoacetamide derivatives on mutants of squalene-hopene cyclase
Lipids
40
729-735
2005
Alicyclobacillus acidocaldarius
Nakano, S.; Ohashi, S.; Hoshino, T.
Squalene-hopene cyclase: insight into the role of the methyl group on the squalene backbone upon the polycyclization cascade. Enzymatic cyclization products of squalene analogs lacking a 26-methyl group and possessing a methyl group at C7 or C11
Org. Biomol. Chem.
2
2012-2022
2004
Alicyclobacillus acidocaldarius
Tanaka, H.; Noguchi, H.; Abe, I.
Enzymatic formation of indole-containing unnatural cyclic polyprenoids by bacterial squalene:hopene cyclase
Org. Lett.
7
5873-5876
2005
Alicyclobacillus acidocaldarius
Morikubo, N.; Fukuda, Y.; Ohtake, K.; Shinya, N.; Kiga, D.; Sakamoto, K.; Asanuma, M.; Hirota, H.; Yokoyama, S.; Hoshino, T.
Cation-pi interaction in the polyolefin cyclization cascade uncovered by incorporating unnatural amino acids into the catalytic sites of squalene cyclase
J. Am. Chem. Soc.
128
13184-13194
2006
Alicyclobacillus acidocaldarius
Tanaka, H.; Noma, H.; Noguchi, H.; Abe, I.
Enzymatic formation of pyrrole-containing novel cyclic polyprenoids by bacterial squalene:hopene cyclase
Tetrahedron Lett.
47
3085-3089
2006
Alicyclobacillus acidocaldarius
-
Schwab, F.; van Gunsteren, W.F.; Zagrovic, B.
Computational study of the mechanism and the relative free energies of binding of anticholesteremic inhibitors to squalene-hopene cyclase
Biochemistry
47
2945-2951
2008
Alicyclobacillus acidocaldarius (P33247)
Hoshino, T.; Kumai, Y.; Sato, T.
Reviewing the polyolefin cyclization reaction of the C(35) polyprene catalyzed by squalene-hopene cyclase
Chemistry
15
2091-2100
2009
Alicyclobacillus acidocaldarius
Ermondi, G.; Caron, G.
GRIND-based 3D-QSAR to predict inhibitory activity for similar enzymes, OSC and SHC
Eur. J. Med. Chem.
43
1462-1468
2008
Alicyclobacillus acidocaldarius
Ghimire, G.; Oh, T.; Lee, H.; Sohng, J.
Squalene-hopene cyclase (Spterp25) from Streptomyces peucetius: Sequence analysis, expression and functional characterization
Biotechnol. Lett.
31
565-569
2009
Streptomyces peucetius (B1PT66), Streptomyces peucetius
Pearson, A.; Leavitt, W.; Saenz, J.; Summons, R.; Tam, M.; Close, H.
Diversity of hopanoids and squalene-hopene cyclases across a tropical land-sea gradient
Environ. Microbiol.
11
1208-1223
2009
Candidatus Kuenenia stuttgartiensis
Cheng, J.; Hoshino, T.
Cyclization cascade of the C33-bisnorheptaprenoid catalyzed by recombinant squalene cyclase
Org. Biomol. Chem.
7
1689-1699
2009
Alicyclobacillus acidocaldarius
Siedenburg, G.; Jendrossek, D.
Squalene-hopene cyclases
Appl. Environ. Microbiol.
77
3905-3915
2011
Alicyclobacillus acidocaldarius, Alicyclobacillus acidocaldarius (P33247), Bradyrhizobium japonicum, Methylococcus capsulatus, Rhodopseudomonas palustris, Streptomyces peucetius, Tetrahymena thermophila, Zymomonas mobilis, no activity in Methylococcus capsulatus
Siedenburg, G.; Breuer, M.; Jendrossek, D.
Prokaryotic squalene-hopene cyclases can be converted to citronellal cyclases by single amino acid exchange
Appl. Microbiol. Biotechnol.
97
1571-1580
2013
Bradyrhizobium japonicum, Rhodopseudomonas palustris, Teredinibacter turnerae, Syntrophobacter fumaroxidans (A0LJS0), Alicyclobacillus acidocaldarius (P33247), Zymomonas mobilis (P33990), Zymomonas mobilis (Q5NM88), Burkholderia ambifaria (Q0B2H5), Burkholderia ambifaria (Q0B5S3), Bacillus anthracis (Q81YD8), Streptomyces coelicolor (Q9X7V9), Acetobacter pasteurianus (YP3187836), Burkholderia ambifaria ATCC BAA-244 / AMMD (Q0B2H5), Burkholderia ambifaria ATCC BAA-244 / AMMD (Q0B5S3), Zymomonas mobilis ATCC 31821 (P33990), Zymomonas mobilis CP4 (Q5NM88), Alicyclobacillus acidocaldarius DSM 446 (P33247)
Seitz, M.; Syren, P.; Steiner, L.; Klebensberger, J.; Nestl, B.; Hauer, B.
Synthesis of heterocyclic terpenoids by promiscuous squalene-hopene cyclases
ChemBioChem
14
436-439
2013
Alicyclobacillus acidocaldarius, Zymomonas mobilis
Hammer, S.C.; Syren, P.O.; Seitz, M.; Nestl, B.M.; Hauer, B.
Squalene hopene cyclases: highly promiscuous and evolvable catalysts for stereoselective CC and CX bond formation
Curr. Opin. Chem. Biol.
17
293-300
2013
Alicyclobacillus acidocaldarius
Seitz, M.; Klebensberger, J.; Siebenhaller, S.; Breuer, M.; Siedenburg, G.; Jendrossek, D.; Hauer, B.
Substrate specificity of a novel squalene-hopene cyclase from Zymomonas mobilis
J. Mol. Catal. B
84
72-77
2012
Zymomonas mobilis (Q5NM88), Zymomonas mobilis CP4 (Q5NM88)
-
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.
10
440-446
2012
Alicyclobacillus acidocaldarius
Englund, E.; Pattanaik, B.; Ubhayasekera, S.J.; Stensjoe, K.; Bergquist, J.; Lindberg, P.
Production of squalene in Synechocystis sp. PCC 6803
PLoS ONE
9
e90270
2014
Synechocystis sp. (P73914), Synechocystis sp.
Hammer, S.; Dominicus, J.; Syrén, P.; Nestl, B.; Hauer, B.
Stereoselective Friedel-Crafts alkylation catalyzed by squalene hopene cyclases
Tetrahedron
68
7624-7629
2012
Zymomonas mobilis (Q5NM88), Zymomonas mobilis CP4 (Q5NM88)
-
Pan, J.; Solbiati, J.; Ramamoorthy, G.; Hillerich, B.; Seidel, R.; Cronan, J.; Almo, S.; Poulter, C.
Biosynthesis of squalene from farnesyl diphosphate in Bacteria Three steps catalyzed by three enzymes
ACS Cent. Sci.
1
77-82
2015
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
Eichhorn, E.; Locher, E.; Guillemer, S.; Wahler, D.; Fourage, L.; Schilling, B.
Biocatalytic process for (-)-ambrox production using squalene hopene cyclase
Adv. Synth. Catal.
360
2339-2351
2018
Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 (P33247)
-
Kuehnel, L.C.; Nestl, B.M.; Hauer, B.
Enzymatic addition of alcohols to terpenes by squalene hopene cyclase variants
ChemBioChem
18
2222-2225
2017
Alicyclobacillus acidocaldarius subsp. acidocaldarius (P33247)
Ideno, N.; Umeyama, S.; Watanabe, T.; Nakajima, M.; Sato, T.; Hoshino, T.
Alicyclobacillus acidocaldarius squalene-hopene cyclase the critical role of steric bulk at Ala306 and the first enzymatic synthesis of epoxydammarane from 2,3-oxidosqualene
ChemBioChem
19
1873-1886
2018
Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 (P33247)
Bastian, S.; Hammer, S.; Kre, N.; Nestl, B.; Hauer, B.
Selectivity in the cyclization of citronellal introduced by squalene hopene cyclase variants
ChemCatChem
9
4364-4368
2017
Alicyclobacillus acidocaldarius
-
Kaneko, I.; Terasawa, Y.; Hoshino, T.
Squalene-hopene cyclase mechanistic insights into the polycyclization cascades of squalene analogs bearing ethyl and hydroxymethyl groups at the C-2 and C-23 positions
Chemistry
24
11139-11157
2018
Alicyclobacillus acidocaldarius
Steudle, A.K.; Nestl, B.M.; Hauer, B.; Stubenrauch, C.
Activity of squalene-hopene cyclases in bicontinuous microemulsions
Colloids Surf. B Biointerfaces
135
735-741
2015
Alicyclobacillus acidocaldarius
Syren, P.O.; Henche, S.; Eichler, A.; Nestl, B.M.; Hauer, B.
Squalene-hopene cyclases-evolution, dynamics and catalytic scope
Curr. Opin. Struct. Biol.
41
73-82
2016
Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 (P33247)
Takahashi, K.; Sasaki, Y.; Hoshino, T.
Squalene-hopene cyclase on the polycyclization reactions of squalene analogues bearing ethyl groups at positions C-6, C-10, C-15, and C-19
Eur. J. Org. Chem.
2018
1477-1490
2018
Alicyclobacillus acidocaldarius
-
Hammer, S.C.; Marjanovic, A.; Dominicus, J.M.; Nestl, B.M.; Hauer, B.
Squalene hopene cyclases are protonases for stereoselective Bronsted acid catalysis
Nat. Chem. Biol.
11
121-126
2015
Alicyclobacillus acidocaldarius (P33247)
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