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2,6-Dimethyl-N-tridecylmorpholine
2-Aza-2-dihydrosqualene
-
-
3beta-Aminocycloeucalene
-
0.2 mM, weak
4beta-Methylcycloeucalenol
-
0.2 mM, weak
7-Keto-24,28-dihydrocycloeucalenol
-
-
7-Oxo-24ksi(28)-dihydrocycloeucalenol
-
reversible, highly specific
7alpha-Hydroxy-24,28-dihydrocycloeucalenol
-
-
7beta-Hydroxy-24,28-dihydrocycloeucalenol
-
-
Cycloartenol
-
0.2 mM, weak
Cycloeucalenyl 3beta-methyl ether
-
0.2 mM, weak
DELTA6-24,28-Dihydrocycloeucalenol
-
-
DELTA7-24,28-Dihydrocycloeucalenol
-
-
N-(1,5,9-Trimethyldecyl)-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol
N-Benzyl-8-aza-4alpha,10-dimethyl-trans-decal-3beta-ol
2,6-Dimethyl-N-tridecylmorpholine
-
-
2,6-Dimethyl-N-tridecylmorpholine
-
systemic fungicide, strong inhibitor
N-(1,5,9-Trimethyldecyl)-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol
-
and derivatives
N-(1,5,9-Trimethyldecyl)-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol
-
and derivatives
N-Benzyl-8-aza-4alpha,10-dimethyl-trans-decal-3beta-ol
-
an analogue of a carbocationic high energy intermediate
N-Benzyl-8-aza-4alpha,10-dimethyl-trans-decal-3beta-ol
-
an analogue of a carbocationic high energy intermediate
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0.077 - 1.53
cycloeucalenol
0.077
cycloeucalenol
-
mutant E29D, 30°C, pH not specified in the publication, Vmax: 0.24 nmol/h/mg
0.078
cycloeucalenol
-
mutant D260H, 30°C, pH not specified in the publication, Vmax: 0.35 nmol/h/mg
0.093
cycloeucalenol
-
mutant E29H, 30°C, pH not specified in the publication, Vmax: 0.33 nmol/h/mg
0.135
cycloeucalenol
-
mutant W112L, 30°C, pH not specified in the publication, Vmax: 14.7 nmol/h/mg
0.167
cycloeucalenol
-
wild-type, 30°C, pH not specified in the publication, Vmax: 22 nmol/h/mg
0.377
cycloeucalenol
-
mutant F111L, 30°C, pH not specified in the publication, Vmax: 4.7 nmol/h/mg
0.409
cycloeucalenol
-
mutant D260E, 30°C, pH not specified in the publication, Vmax: 44 nmol/h/mg
0.496
cycloeucalenol
-
mutant T113S, 30°C, pH not specified in the publication, Vmax: 26 nmol/h/mg
0.52
cycloeucalenol
-
mutant F117L, 30°C, pH not specified in the publication, Vmax: 5.3 nmol/h/mg
0.622
cycloeucalenol
-
mutant G108A, 30°C, pH not specified in the publication, Vmax: 11.4 nmol/h/mg
1.53
cycloeucalenol
-
mutant T113A, 30°C, pH not specified in the publication, Vmax: 4.9 nmol/h/mg
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D260E
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 92%, wild-type: 100%. Relative activity: 135% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type. Mutant shows 6% activity with 24-methylene-24-dihydro-cycloartenol (wild-type 0%)
D260H
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 61%, wild-type: 100%. Relative activity: 5.2% (wild-type: 100%). Km (cycloeucalenol) decreased compared to wild-type
D260V
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 0%, wild-type: 100%. Relative activity: below 1.5% (wild-type: 100%)
D260Y
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 22%, wild-type: 100%. Relative activity: 0.7% (wild-type: 100%)
E29D
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 65%, wild-type: 100%. Relative activity: 3.8% (wild-type: 100%). Km (cycloeucalenol) decreased compared to wild-type
E29H
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 33%, wild-type: 100%. Relative activity: 3.5% (wild-type: 100%). Km (cycloeucalenol) decreased compared to wild-type
E29V
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 0%, wild-type: 100%. Relative activity: below 0.5% (wild-type: 100%)
E54V
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 94%, wild-type: 100%
E58V
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 91%, wild-type: 100%
E60V
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 83%, wild-type: 100%
F111L
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 88%, wild-type: 100%. Relative activity: 31% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
F116L
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 37%, wild-type: 100%. Relative activity: 4.7% (wild-type: 100%)
F117L
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 89%, wild-type: 100%. Relative activity: 28% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
G108A
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 92%, wild-type: 100%. Relative activity: 90% (wild-type: 100%)
G108V
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 6%, wild-type: 100%. Relative activity: 1.7% (wild-type: 100%)
G28V
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 46%, wild-type: 100%. Relative activity: 1.6% (wild-type: 100%)
H114L
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 85%, wild-type: 100%. Relative activity: 5.2% (wild-type: 100%)
N109A
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 76%, wild-type: 100%. Relative activity: 4.6% (wild-type: 100%)
T113A
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 69%, wild-type: 100%. Relative activity: 7.2% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
T113S
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 98%, wild-type: 100%. Relative activity: 73% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
W112E
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 77%, wild-type: 100%. Relative activity: 5.8% (wild-type: 100%)
W112K
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 47%, wild-type: 100%. Relative activity: 1.8% (wild-type: 100%)
W112L
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 86%, wild-type: 100%. Relative activity: 49% (wild-type: 100%). Km (cycloeucalenol) decreased compared to wild-type. Mutant shows 69% activity with 24-methylene-24-dihydro-cycloartenol (wild-type 0%), 10% activity with cycloartenol (wild-type 0%). 32% activity with cycloartanol (wild-type 0%), 15% activity with 4beta-methyl-24-dihydro-cycloeucalenol (wild-type 0%)
Y110L
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 64%, wild-type: 100%. Relative activity: 2.8% (wild-type: 100%)
Y115L
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 83%, wild-type: 100%. Relative activity: 4.3% (wild-type: 100%)
E29K
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 1.7%, wild-type: 100%. Relative activity: below 0.5% (wild-type: 100%)
E29K
-
in vivo conversion of cycloeucalenol into ergosterol and in vitro CPI activity in Saccharomyces cerevisiae erg7 transformants carrying Arabidopsis thaliana mutant CPI: 1.7% relative ergosterol synthesis (wild-type: 100%), below 0.5% in vitro microsomal CPI activity (wild-type: 100%)
G108E
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 0%, wild-type: 100%. Relative activity: below 0.5% (wild-type: 100%). Km (cycloeucalenol) increased compared to wild-type
G108E
-
in vivo conversion of cycloeucalenol into ergosterol and in vitro CPI activity in Saccharomyces cerevisiae erg7 transformants carrying Arabidopsis thaliana mutant CPI: 0% relative ergosterol synthesis (wild-type: 100%), below 0.5% in vitro microsomal CPI activity (wild-type: 100%)
G28E
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 15%, wild-type: 100%. Relative activity: 1% (wild-type: 100%)
G28E
-
in vivo conversion of cycloeucalenol into ergosterol and in vitro CPI activity in Saccharomyces cerevisiae erg7 transformants carrying Arabidopsis thaliana mutant CPI: 15% relative ergosterol synthesis (wild-type: 100%), 1% in vitro microsomal CPI activity (wild-type: 100%)
T113I
-
cycloeucalenol conversion into ergosterol in Saccharomyces cerevisiae erg7 transformants carrying mutagenized AtCPI, relative ergosterol synthesis: 66%, wild-type: 100%. Relative activity: 3.1% (wild-type: 100%)
T113I
-
in vivo conversion of cycloeucalenol into ergosterol and in vitro CPI activity in Saccharomyces cerevisiae erg7 transformants carrying Arabidopsis thaliana mutant CPI: 66% relative ergosterol synthesis (wild-type: 100%), below 2.4% in vitro microsomal CPI activity (wild-type: 100%)
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Rahier, A.; Schmitt, P.; Benveniste, P.
7-Oxo-24ksi(28)-Dihydrocycloeucalenol, a potent inhibitor of plant sterol biosynthesis
Phytochemistry
21
1969-1974
1982
Zea mays
-
brenda
Rahier, A.; Cattel, L.; Benveniste, P.
Mechanism of the enzymatic cleavage of the 9beta,19-cyclopropane ring of cycloeucalenol
Phytochemistry
16
1187-1192
1977
Zea mays
-
brenda
Rahier, A.; Taton, M.; Beneviste, P.
Cycloeucalenol-obtusifoliol isomerase
Eur. J. Biochem.
181
615-626
1989
Zea mays
brenda
Heintz, R.; Benveniste, P.
Plant sterol metabolism. Enzymatic cleavage of the 9beta,19beta-cyclopropane ring of cyclopropyl sterols in bramble tissue cultures
J. Biol. Chem.
249
4267-4274
1974
Nicotiana tabacum, no activity in Oryctolagus cuniculus, Pisum sativum, Rubus plicatus
brenda
Rahier, A.; Bouvier, P.; Cattel, L.; Narula, A.; Benveniste, P.
Inhibition of 2,3-oxidosqualene: beta-amyrin-cyclase, S-adenosyl-L-methionine:cycloartenol C-24-methyltransferase and cycloeucalenol:obtusifoliol isomerase by rationally designed molecules containing a tertiary amine function
Biochem. Soc. Trans.
11
537-543
1983
Rubus plicatus, Zea mays
brenda
Bladocha, M.; Benveniste, P.
Manipulation by tridemorph, a systemic fungicide, of the sterol composition of maize leaves and roots
Plant Physiol.
71
756-762
1983
Zea mays
brenda
Taton, M.; Benveniste, P.; Rahier, A.
Comparative study of the inhibition of sterol biosynthesis in Rubus fruticosus suspension cultures and Zea mays seedlings by N-(1,5,9-trimethyldecyl)-4alpha,10-dimethyl-8-aza-trans-decal-3beta-ol and derivatives
Phytochemistry
26
385-392
1987
Rubus plicatus, Zea mays
-
brenda
Rahier, A.; Taton, M.; Schmitt, P.; Benveniste, P.; Place, P.; Anding, C.
Inhibition of DELTA8->DELTA7-sterol isomerase and of cycloeucalenol-obtusifoliol isomerase by N-benzyl-8-aza-4alpha,10-dimethyl-trans-decal-3beta-ol, an analogue of a carbocationic high energy intermediate
Phytochemistry
24
1223-1232
1985
Rubus plicatus, Zea mays
-
brenda
Hartmann-Bouillon, M.A.; Benveniste, P.
Sterol biosynthetic capability of purified membrane fractions from maize coleoptiles
Phytochemistry
17
1037-1042
1978
Zea mays
-
brenda
Lovato, M.A.; Hart, E.A.; Segura, M.J.R.; Giner, J.L.; Matsuda, S.P.T.
Functional cloning of an Arabidopsis thaliana cDNA encoding cycloeucalenol cycloisomerase
J. Biol. Chem.
275
13394-13397
2000
Arabidopsis thaliana (Q9M643), Arabidopsis thaliana
brenda
Rahier, A.; Karst, F.
Plant cyclopropylsterol-cycloisomerase: key amino acids affecting activity and substrate specificity
Biochem. J.
459
289-299
2014
Arabidopsis thaliana
brenda