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Literature summary for 2.3.1.140 extracted from

  • Sander, M.; Petersen, M.
    Distinct substrate specificities and unusual substrate flexibilities of two hydroxycinnamoyltransferases, rosmarinic acid synthase and hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyl-transferase, from Coleus blumei Benth. (2011), Planta, 233, 1157-1171.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene cbras, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression of His-tagged RAS in Escherichia coli strain BL21(DE3)pLysS Coleus scutellarioides

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0013
-
4-coumaroyl-CoA pH 7.0, 30°C, with 3-(3,4-dihydroxyphenyl)lactate, native RAS Coleus scutellarioides
0.0018
-
4-coumaroyl-CoA pH 7.0, 30°C, with 3-(3,4-dihydroxyphenyl)lactate, recombinant RAS Coleus scutellarioides
0.0021
-
caffeoyl-CoA pH 7.0, 30°C, with 3-(4-hydroxyphenyl)lactate, recombinant RAS Coleus scutellarioides
0.0034
-
caffeoyl-CoA pH 7.0, 30°C, with 3-(4-hydroxyphenyl)lactate, native RAS Coleus scutellarioides
0.0035
-
caffeoyl-CoA pH 7.0, 30°C, with D-phenyllactate, recombinant RAS Coleus scutellarioides
0.0039
-
caffeoyl-CoA pH 7.0, 30°C, with 3-(3,4-dihydroxyphenyl)lactate, recombinant RAS Coleus scutellarioides
0.004
-
caffeoyl-CoA pH 7.0, 30°C, with 3-(3,4-dihydroxyphenyl)lactate, native RAS Coleus scutellarioides
0.0047
-
4-coumaroyl-CoA pH 7.0, 30°C, with 3-(4-hydroxyphenyl)lactate, native RAS Coleus scutellarioides
0.0092
-
4-coumaroyl-CoA pH 7.0, 30°C, with 3-(4-hydroxyphenyl)lactate, recombinant RAS Coleus scutellarioides
0.0107
-
4-coumaroyl-CoA pH 7.0, 30°C, with D-phenyllactate, recombinant RAS Coleus scutellarioides
0.0158
-
cinnamoyl-CoA pH 7.0, 30°C, with 3-(3,4-dihydroxyphenyl)lactate, recombinant RAS Coleus scutellarioides
0.0191
-
feruloyl-CoA pH 7.0, 30°C, with 3-(3,4-dihydroxyphenyl)lactate, recombinant RAS Coleus scutellarioides
0.025
-
3-(4-hydroxyphenyl)lactate pH 7.0, 30°C, with 4-coumaroyl-CoA, recombinant RAS Coleus scutellarioides
0.0255
-
cinnamoyl-CoA pH 7.0, 30°C, with 3-(4-hydroxyphenyl)lactate, recombinant RAS Coleus scutellarioides
0.035
-
3-(3,4-Dihydroxyphenyl)lactate pH 7.0, 30°C, with 4-coumaroyl-CoA, recombinant RAS Coleus scutellarioides
0.0364
-
feruloyl-CoA pH 7.0, 30°C, with 3-(4-hydroxyphenyl)lactate, recombinant RAS Coleus scutellarioides
0.0529
-
cinnamoyl-CoA pH 7.0, 30°C, with D-phenyllactate, recombinant RAS Coleus scutellarioides
0.0817
-
4-coumaroyl-CoA pH 7.0, 30°C, with D-tyrosine, recombinant RAS Coleus scutellarioides
0.0945
-
caffeoyl-CoA pH 7.0, 30°C, with D-tyrosine, recombinant RAS Coleus scutellarioides
0.163
-
3-(4-hydroxyphenyl)lactate pH 7.0, 30°C, with caffeoyl-CoA, recombinant RAS Coleus scutellarioides
0.193
-
3-(3,4-Dihydroxyphenyl)lactate pH 7.0, 30°C, with caffeoyl-CoA, recombinant RAS Coleus scutellarioides
0.34
-
3-(3,4-Dihydroxyphenyl)lactate pH 7.0, 30°C, with cinnamoyl-CoA, recombinant RAS Coleus scutellarioides
0.49
-
D-phenyllactate pH 7.0, 30°C, with 4-coumaroyl-CoA, recombinant RAS Coleus scutellarioides
0.55
-
3-(4-hydroxyphenyl)lactate pH 7.0, 30°C, with cinnamoyl-CoA, recombinant RAS Coleus scutellarioides
1.3
-
3-(3,4-Dihydroxyphenyl)lactate pH 7.0, 30°C, with feroyl-CoA, recombinant RAS Coleus scutellarioides
1.346
-
D-phenyllactate pH 7.0, 30°C, with cinnamoyl-CoA, recombinant RAS Coleus scutellarioides
1.425
-
3-(4-hydroxyphenyl)lactate pH 7.0, 30°C, with feroyl-CoA, recombinant RAS Coleus scutellarioides
17.82
-
D-phenyllactate pH 7.0, 30°C, with caffeoyl-CoA, recombinant RAS Coleus scutellarioides

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
caffeoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate Coleus scutellarioides via intermediate 4-coumaroyl-4'-hydroxyphenyllactic acid CoA + rosmarinate
-
?

Organism

Organism UniProt Comment Textmining
Coleus scutellarioides
-
gene cbras
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged RAS from Escherichia coli strain BL21(DE3)pLysS by nickel affinity chromatography, dialysis, and cleavage of the tag by thrombin followed by His affinity chromatography to eliminate the tag Coleus scutellarioides

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-coumaroyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
-
Coleus scutellarioides CoA + 2-O-(4-coumaroyl)-3-(3,4-dihydroxyphenyl)lactate
-
?
4-coumaroyl-CoA + 3-(4-hydroxyphenyl)lactate
-
Coleus scutellarioides CoA + 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactate
-
?
4-coumaroyl-CoA + D-phenyllactate
-
Coleus scutellarioides CoA + (R)-2-O-(4-coumaroyl)-3-phenyllactate
-
?
4-coumaroyl-CoA + D-tyrosine
-
Coleus scutellarioides CoA + N-(4-coumaroyl)-D-tyrosine
-
?
caffeoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
-
Coleus scutellarioides CoA + rosmarinate
-
?
caffeoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate via intermediate 4-coumaroyl-4'-hydroxyphenyllactic acid Coleus scutellarioides CoA + rosmarinate
-
?
caffeoyl-CoA + 3-(4-hydroxyphenyl)lactate
-
Coleus scutellarioides CoA + 2-O-caffeoyl-3-(4-hydroxyphenyl)lactate
-
?
caffeoyl-CoA + D-phenyllactate
-
Coleus scutellarioides CoA + (R)-2-O-caffeoyl-3-phenyllactate
-
?
caffeoyl-CoA + D-tyrosine
-
Coleus scutellarioides CoA + N-caffeoyl-D-tyrosine
-
?
cinnamoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
-
Coleus scutellarioides CoA + 2-O-cinnamoyl-3-(3,4-dihydroxyphenyl)lactate
-
?
cinnamoyl-CoA + 3-(4-hydroxyphenyl)lactate
-
Coleus scutellarioides CoA + 2-O-cinnamoyl-3-(4-hydroxyphenyl)lactate
-
?
cinnamoyl-CoA + D-phenyllactate
-
Coleus scutellarioides CoA + (R)-2-O-cinnamoyl-3-phenyllactate
-
?
feruloyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
-
Coleus scutellarioides CoA + 2-O-feruloyl-3-(3,4-dihydroxyphenyl)lactate
-
?
feruloyl-CoA + 3-(4-hydroxyphenyl)lactate
-
Coleus scutellarioides CoA + 2-O-feruloyl-3-(4-hydroxyphenyl)lactate
-
?
additional information CbRAS accepts several CoA-activated phenylpropenoic acids as donor substrates and D-(hydroxy)phenyllactates as acceptors resulting in ester formation while shikimate and quinate are not accepted. Amino acids, such as D-phenylalanine, D-tyrosine, and D-DOPA, also yielded products, showing that RAS can putatively catalyze amide formation Coleus scutellarioides ?
-
?
sinapoyl-CoA + 3-(4-hydroxyphenyl)lactate
-
Coleus scutellarioides CoA + 2-O-sinapoyl-3-(4-hydroxyphenyl)lactate
-
?

Synonyms

Synonyms Comment Organism
hydroxycinnamoyl-CoA:hydroxyphenyllactate hydroxycinnamoyltransferase
-
Coleus scutellarioides
RAS
-
Coleus scutellarioides
rosmarinic acid synthase
-
Coleus scutellarioides

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Coleus scutellarioides

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
assay at Coleus scutellarioides

General Information

General Information Comment Organism
evolution RAS belongs to the large plant acyl-CoA-dependent BAHD acyltransferase superfamily characterized by mostly conserved sequence motifs, the HxxxD(G) motif containing the catalytically active histidine residue and the DFGWG motif close to the C terminus, phylogenetic analysis, overview Coleus scutellarioides