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(3R)-Squalene epoxide
Epilanosterol
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
achilleol A
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol + (13alphaH)-isomalabarica-14(26),17E,21-trien-3beta-ol
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reaction of mutant V454I
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol + (13alphaH)-isomalabarica-14(26),17E,21-trien-3beta-ol + protosta-16,24-dien-3beta-ol
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reaction of mutant Q450H/V454I
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol + achilleol A
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reaction of C457G/T509G
achilleol A is the main product
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol + achilleol A + 13alphaH-isomalabarica-14(26),17E,21-trien-3beta-ol
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reaction of mutant H234W/Y510V
lanosterol is the main product
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol + parkeol + 9beta-lanosta-7,24-dien-3beta-ol
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reaction of mutants T384Y, T384Y/Q450H, and T384Y/V454I
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
(3S)-2,3-epoxy-2,3-dihydrosqualene
protosta-12,24-dien-3-beta-ol
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reaction of mutant H232T
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?
(3S)-2,3-oxidosqualene
?
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two essential histidine residues per active site are necessary for complete activity
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?
(3S)-2,3-oxidosqualene
lanosterol
(3S)-squalene-2,3-epoxide
lanosterol
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?
(S)-2,3-epoxysqualene
lanosterol
(S)-2,3-oxidosqualene
lanosterol
(S)-squalene-2,3-epoxide
Lanosterol
2,3-monoepoxysqualene
lanosterol
2,3-oxidosqualene
lanosterol
2,3:22,23-diepoxysqualene
24(S),25-epoxylanosterol
27-norsqualene
30-norlanosterol + 26-normalabaricatriene
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?
29-norsqualene
(2S,4aS,6aR,7R,10aR,12aR)-1,1,4a,6a,10a-pentamethyl-7-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,5,6,6a,7,8,9,10,10a,11,12,12a-hexadecahydrochrysen-2-ol + (2S,4aS,6aS,7R,10aS,12aR)-1,1,4a,6a,10a-pentamethyl-7-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,5,6,6a,7,8,9,10,10a,11,12,12a-hexadecahydrochrysen-2-ol
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?
3-[(3E,7E,15E)-16-ethyl-3,7,12,20-tetramethylhenicosa-3,7,11,15,19-pentaen-1-yl]-2,2-dimethyloxirane
?
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ethylation at C10 or C15
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?
dioxidosqualene
24(S),25-epoxylanosterol
oxidosqualene
lanosterol
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?
additional information
?
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(3S)-2,3-epoxy-2,3-dihydrosqualene
achilleol A
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reaction of mutant H234W/Y510W
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
achilleol A
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reaction of mutant Q450H
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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r
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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r
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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r
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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reaction of wild-type enzyme, via intermediates parkeol and protosta-12,24-dien-3-beta-ol
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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reaction of wild-type enzyme
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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r
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
lanosterol
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the enzyme performs the polycyclization reaction by folding the substrate in a chair-boat-chair-chair conformation
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
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reaction of mutant H232S
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
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reaction of mutant T384Y/Q450H/V454I
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?
(3S)-2,3-oxidosqualene
lanosterol
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?
(3S)-2,3-oxidosqualene
lanosterol
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?
(3S)-2,3-oxidosqualene
lanosterol
reaction is completely regio- and stereospecific
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?
(3S)-2,3-oxidosqualene
lanosterol
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?
(3S)-2,3-oxidosqualene
lanosterol
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?
(3S)-2,3-oxidosqualene
lanosterol
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?
(3S)-2,3-oxidosqualene
lanosterol
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?
(3S)-Squalene epoxide
?
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?
(3S)-Squalene epoxide
?
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?
(S)-2,3-epoxysqualene
lanosterol
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?
(S)-2,3-epoxysqualene
lanosterol
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formation of lanosterol the first sterol precursor of cholesterol in mammals
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?
(S)-2,3-epoxysqualene
lanosterol
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synthesis of about 0.1% parkeol as byproduct
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?
(S)-2,3-epoxysqualene
lanosterol
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no other product observed
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?
(S)-2,3-epoxysqualene
lanosterol
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?
(S)-2,3-epoxysqualene
lanosterol
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?
(S)-2,3-epoxysqualene
lanosterol
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lanosterol is the only product in wild-type
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?
(S)-2,3-oxidosqualene
lanosterol
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?
(S)-2,3-oxidosqualene
lanosterol
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?
(S)-2,3-oxidosqualene
lanosterol
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?
(S)-2,3-oxidosqualene
lanosterol
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?
(S)-2,3-oxidosqualene
lanosterol
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?
(S)-2,3-oxidosqualene
lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
(S)-squalene-2,3-epoxide
Lanosterol
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?
2,3-monoepoxysqualene
lanosterol
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?
2,3-monoepoxysqualene
lanosterol
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?
2,3-monoepoxysqualene
lanosterol
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?
2,3-monoepoxysqualene
lanosterol
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?
2,3-oxidosqualene
lanosterol
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?
2,3-oxidosqualene
lanosterol
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?
2,3-oxidosqualene
lanosterol
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?
2,3-oxidosqualene
lanosterol
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?
2,3-oxidosqualene
lanosterol
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?
2,3:22,23-diepoxysqualene
24(S),25-epoxylanosterol
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?
2,3:22,23-diepoxysqualene
24(S),25-epoxylanosterol
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this reaction is enhanced when OSC is inhibited
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?
2,3:22,23-diepoxysqualene
24(S),25-epoxylanosterol
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?
2,3:22,23-diepoxysqualene
24(S),25-epoxylanosterol
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?
2,3:22,23-diepoxysqualene
24(S),25-epoxylanosterol
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?
2,3:22,23-diepoxysqualene
24(S),25-epoxylanosterol
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?
2,3:22,23-diepoxysqualene
24(S),25-epoxylanosterol
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this reaction is enhanced when OSC is inhibited
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?
dioxidosqualene
24(S),25-epoxylanosterol
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?
dioxidosqualene
24(S),25-epoxylanosterol
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?
squalene
?
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?
additional information
?
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central role in sterol biosynthesis
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?
additional information
?
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central role in sterol biosynthesis
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?
additional information
?
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mutant enzyme display altered product profiles compared to the wild-type enzyme producing also e.g. achilleol A, camelliol C, 13alphaH-isomalabarica-14(26),17E,21-trien-3beta-ol, protosta-12(13),24-dien-3beta-ol, protosta-13(17),24-dien-3beta-ol, or parkeol, overview
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?
additional information
?
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trypanosome and animal lanosterol synthases use different catalytic motifs
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?
additional information
?
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trypanosome and animal lanosterol synthases use different catalytic motifs
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?