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Literature summary for 4.3.3.2 extracted from

  • Stoeckigt, J.; Barleben, L.; Panjikar, S.; Loris, E.A.
    3D-Structure and function of strictosidine synthase - the key enzyme of monoterpenoid indole alkaloid biosynthesis (2008), Plant Physiol. Biochem., 46, 340-355.
    View publication on PubMed

Protein Variants

Protein Variants Comment Organism
V208A the mutant shows altered substrate specificity compared to the wild-type enzyme, e.g. increased activity with tryptamine, overview Rauvolfia serpentina

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.007
-
tryptamine
-
Catharanthus roseus
0.072
-
tryptamine wild-type enzyme Rauvolfia serpentina
0.219
-
tryptamine mutant V208A Rauvolfia serpentina
1.036
-
serotonin wild-type enzyme Rauvolfia serpentina

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
tryptamine + secologanin Rauvolfia serpentina the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview 3-alpha(S)-strictosidine + H2O
-
?
tryptamine + secologanin Catharanthus roseus the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview 3-alpha(S)-strictosidine + H2O
-
?

Organism

Organism UniProt Comment Textmining
Catharanthus roseus P18417
-
-
Rauvolfia serpentina P68175
-
-

Reaction

Reaction Comment Organism Reaction ID
3-alpha(S)-strictosidine + H2O = tryptamine + secologanin catalytic reaction mechanism Rauvolfia serpentina

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-(2-aminoethyl)-benzothiophene + secologanin
-
Catharanthus roseus ? + H2O
-
?
3-[(tert-butoxycarbonyl)amino]propyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + secologanin competitive to strictosidine Rauvolfia serpentina ? + H2O
-
?
4-fluorotryptamine + secologanin
-
Catharanthus roseus 4-fluoro-3-alpha(S)-strictosidine + H2O
-
?
4-methyltryptamine + secologanin
-
Catharanthus roseus 4-methyl-3-alpha(S)-strictosidine + H2O
-
?
5,6-dihydroxytryptamine + secologanin
-
Rauvolfia serpentina ? + H2O
-
?
5-fluorotryptamine + secologanin
-
Rauvolfia serpentina 5-fluoro-3-alpha(S)-strictosidine + H2O
-
?
5-fluorotryptamine + secologanin
-
Catharanthus roseus 5-fluoro-3-alpha(S)-strictosidine + H2O
-
?
6-fluorotryptamine + secologanin
-
Rauvolfia serpentina 6-fluoro-3-alpha(S)-strictosidine + H2O
-
?
6-fluorotryptamine + secologanin
-
Catharanthus roseus 6-fluoro-3-alpha(S)-strictosidine + H2O
-
?
6-methoxyltryptamine + secologanin
-
Rauvolfia serpentina 6-methoxy-3-alpha(S)-strictosidine + H2O
-
?
6-methyltryptamine + secologanin
-
Rauvolfia serpentina 6-methyl-3-alpha(S)-strictosidine + H2O
-
?
6-methyltryptamine + secologanin
-
Catharanthus roseus 6-methyl-3-alpha(S)-strictosidine + H2O
-
?
7-fluorotryptamine + secologanin
-
Catharanthus roseus 7-fluoro-3-alpha(S)-strictosidine + H2O
-
?
7-methyltryptamine + secologanin
-
Rauvolfia serpentina 7-methyl-3-alpha(S)-strictosidine + H2O
-
?
7-methyltryptamine + secologanin
-
Catharanthus roseus 7-methyl-3-alpha(S)-strictosidine + H2O
-
?
but-3-yn-1-yl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + secologanin competitive to strictosidine Rauvolfia serpentina ? + H2O
-
?
additional information substrate specificity, e.g. with tryptamine derivatives, overview. No activity with 2-pyrrole-3-ethylamine, phenylethylamine, tyramine, homoveratrylamine, N-acetyl-5-hydroxytryptamine, N-methyltryptamine, 3-methylamine indole, 3-propylamine indole, 2-methyltryptamine, 2-ethyltryptamine, 5,6-dihydroxytryptamine, 5,7-dimethoxytryptamine, histamine, dopamine, 5-methyltryptamine, 6-methyltryptamine, and 5-methoxytryptamine, overview Catharanthus roseus ?
-
?
additional information substrate specificity, e.g. with tryptamine derivatives, overview. No activity with N-acetyl-5-hydroxytryptamine, N-methyltryptamine, N-omega-methyltryptamine, 2-methyl,5-hydroxytryptamine, 3-methylamine indole, 3-propylamine indole, 2-methyltryptamine, 2-ethyltryptamine, 5,7-dimethoxytryptamine, phenylalanine, histamine, dopamine, 5-methyltryptamine, 5-methoxytryptamine, 4,5-dimethyltryptamine, and 4-methyl-5-methoxytryptamine, and with secologanic acid, tarennoside, 18-n-butylsecologanin, and 18-tert-butylsecologanin, overview. Dihydrosecologanin and secologanin acid ethyl ester are poor substrates Rauvolfia serpentina ?
-
?
prop-2-yn-1-yl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + secologanin competitive to strictosidine Rauvolfia serpentina ? + H2O
-
?
serotonin + secologanin
-
Rauvolfia serpentina 5-hydroxy-3-alpha(S)-strictosidine + H2O
-
?
serotonin + secologanin
-
Catharanthus roseus 5-hydroxy-3-alpha(S)-strictosidine + H2O
-
?
tryptamine + 2'-O-methylsecologanin
-
Rauvolfia serpentina ? + H2O
-
?
tryptamine + 3'-O-methylsecologanin
-
Rauvolfia serpentina ? + H2O
-
?
tryptamine + secologanic acid allyl ester
-
Rauvolfia serpentina ? + H2O
-
?
tryptamine + secologanic acid pentynyl ester
-
Rauvolfia serpentina ? + H2O
-
?
tryptamine + secologanic acid propynyl ester
-
Rauvolfia serpentina ? + H2O
-
?
tryptamine + secologanin the enzyme catalyses the biological Pictete-Spengler reaction of tryptamine and secologanin Catharanthus roseus 3-alpha(S)-strictosidine
-
?
tryptamine + secologanin the enzyme catalyses the biological Pictete-Spengler reaction of tryptamine and secologanin. Tryptamine is located at the bottom of the substrate binding pocket, where its primary amine group is connected with residue Glu309 by a hydrogen bond. The main amino acid residues involved in forming the active centre are Tyr105, Trp149, Val167, Met180, Val208, Phe226, Ser269, Met276, His277, His307, Phe308, Glu309, Leu323, and Phe324 Rauvolfia serpentina 3-alpha(S)-strictosidine
-
?
tryptamine + secologanin the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview Rauvolfia serpentina 3-alpha(S)-strictosidine + H2O
-
?
tryptamine + secologanin the strictosidine synthase plays a central role in the biosynthesis of all structural types of monoterpenoid indole alkaloids, overview Catharanthus roseus 3-alpha(S)-strictosidine + H2O
-
?

Subunits

Subunits Comment Organism
More the overall enzyme structure of STR1 represents a beta-propeller comprising 6 blades, which are radially arranged around a central 6fold pseudo-symmetry axis, containing three helices in the STR1 structure. Each propeller blade contains four beta-strands, which form a twisted, antiparallel beta-sheet, important role of covalently bound cysteine residues in the integrity of the substrate binding site and in the enzyme's overall structure, structure analysis, overview Rauvolfia serpentina

Synonyms

Synonyms Comment Organism
STR1
-
Rauvolfia serpentina
STR1
-
Catharanthus roseus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.002
-
tryptamine
-
Catharanthus roseus
10.65
-
tryptamine wild-type enzyme Rauvolfia serpentina
11.13
-
serotonin wild-type enzyme Rauvolfia serpentina
11.31
-
tryptamine mutant V208A Rauvolfia serpentina