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Literature summary extracted from

  • Weitzel, C.; Petersen, M.
    Cloning and characterisation of rosmarinic acid synthase from Melissa officinalis L. (2011), Phytochemistry, 72, 572-578.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.140 RAS gene, intron-free and single-copy gene, DNA and amino acid sequence determination and analysis, heterologous expression of N-terminally His6-tagged RAS in Escherichia coli strain BL21(DE3)pLysS Melissa officinalis

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.1.140 4-coumaroyl-CoA severe substrate inhibition of 4-coumaroyl-CoA with 3-(4-hydroxyphenyl)lactate as acceptor and less with 3-(3,4-dihydroxyphenyl)lactate Melissa officinalis

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.140 additional information
-
 additional information kinetics, overview Melissa officinalis
2.3.1.140 0.0023
-
 caffeoyl-CoA with 3-(4-hydroxyphenyl)lactate, pH 7.0, 30°C, crude recombinant His-tagged enzyme Melissa officinalis
2.3.1.140 0.0032
-
 4-coumaroyl-CoA with 3-(3,4-dihydroxyphenyl)lactate, pH 7.0, 30°C, crude recombinant His-tagged enzyme Melissa officinalis
2.3.1.140 0.0033
-
 caffeoyl-CoA with 3-(3,4-dihydroxyphenyl)lactate, pH 7.0, 30°C, crude recombinant His-tagged enzyme Melissa officinalis
2.3.1.140 0.0048
-
 4-coumaroyl-CoA with 3-(4-hydroxyphenyl)lactate, pH 7.0, 30°C, native crude enzyme Melissa officinalis
2.3.1.140 0.0052
-
 caffeoyl-CoA with 3-(3,4-dihydroxyphenyl)lactate, pH 7.0, 30°C, native crude enzyme Melissa officinalis
2.3.1.140 0.0058
-
 caffeoyl-CoA with 3-(4-hydroxyphenyl)lactate, pH 7.0, 30°C, native crude enzyme Melissa officinalis
2.3.1.140 0.0073
-
 4-coumaroyl-CoA with 3-(3,4-dihydroxyphenyl)lactate, pH 7.0, 30°C, native crude enzyme Melissa officinalis
2.3.1.140 0.0094
-
 4-coumaroyl-CoA with 3-(4-hydroxyphenyl)lactate, pH 7.0, 30°C, crude recombinant His-tagged enzyme Melissa officinalis
2.3.1.140 0.0169
-
 3-(4-hydroxyphenyl)lactate with 4-coumaroyl-CoA, pH 7.0, 30°C, native crude enzyme Melissa officinalis
2.3.1.140 0.0189
-
 3-(4-hydroxyphenyl)lactate with 4-coumaroyl-CoA, pH 7.0, 30°C, crude recombinant His-tagged enzyme Melissa officinalis
2.3.1.140 0.074
-
 3-(4-hydroxyphenyl)lactate with caffeoyl-CoA, pH 7.0, 30°C, native crude enzyme Melissa officinalis
2.3.1.140 0.0853
-
 3-(3,4-Dihydroxyphenyl)lactate with 4-coumaroyl-CoA, pH 7.0, 30°C, crude recombinant His-tagged enzyme Melissa officinalis
2.3.1.140 0.1528
-
 3-(3,4-Dihydroxyphenyl)lactate with 4-coumaroyl-CoA, pH 7.0, 30°C, native crude enzyme Melissa officinalis
2.3.1.140 0.1565
-
 3-(4-hydroxyphenyl)lactate with caffeoyl-CoA, pH 7.0, 30°C, crude recombinant His-tagged enzyme Melissa officinalis
2.3.1.140 0.2126
-
 3-(3,4-Dihydroxyphenyl)lactate with caffeoyl-CoA, pH 7.0, 30°C, crude recombinant His-tagged enzyme Melissa officinalis
2.3.1.140 0.2336
-
 3-(3,4-Dihydroxyphenyl)lactate with caffeoyl-CoA, pH 7.0, 30°C, native crude enzyme Melissa officinalis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.140 4-coumaroyl-CoA + 3-(3,4-dihydroxyphenyl)lactate Melissa officinalis
-
 CoA + 2-O-(4-coumaroyl)-3-(3,4-dihydroxyphenyl)lactate
-
 ?
2.3.1.140 4-coumaroyl-CoA + 3-(4-hydroxyphenyl)lactate Melissa officinalis
-
 CoA + 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactate the precursor for rosmarinic acid synthesis via further hydroxylations, overview ?
2.3.1.140 caffeoyl-CoA + 3-(4-hydroxyphenyl)lactate Melissa officinalis
-
 CoA + 2-O-caffeoyl-3-(4-hydroxyphenyl)lactate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.140 Melissa officinalis
-
 RAS gene
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.1.140 cell suspension culture RAS activity decreases through the cell cultivation period, it is highest after 3-4 days and completely declined after 11 days, overview. The RAS expression level declines also durring cell cultivation and is almost undetectable after 6-9 days, and absent after 10 days Melissa officinalis
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.140 4-coumaroyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
-
 Melissa officinalis CoA + 2-O-(4-coumaroyl)-3-(3,4-dihydroxyphenyl)lactate
-
 ?
2.3.1.140 4-coumaroyl-CoA + 3-(4-hydroxyphenyl)lactate
-
 Melissa officinalis CoA + 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactate
-
 ?
2.3.1.140 4-coumaroyl-CoA + 3-(4-hydroxyphenyl)lactate
-
 Melissa officinalis CoA + 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactate the precursor for rosmarinic acid synthesis via further hydroxylations, overview ?
2.3.1.140 caffeoyl-CoA + 3-(4-hydroxyphenyl)lactate
-
 Melissa officinalis CoA + 2-O-caffeoyl-3-(4-hydroxyphenyl)lactate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.140 4-coumaroyl-CoA:hydroxyphenyllactic acid hydroxycinnamoyltransferase
-
 Melissa officinalis
2.3.1.140 RAS
-
 Melissa officinalis
2.3.1.140 rosmarinic acid synthase
-
 Melissa officinalis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.140 45
-
 recombinant enzyme Melissa officinalis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.140 7.3
-
 recombinant enzyme Melissa officinalis

General Information

EC Number General Information Comment Organism
2.3.1.140 evolution MoRAS belongs to the BAHD superfamily of acyltransferases, it possesses the two conserved sequence motifs HxxxDG and DFGWG Melissa officinalis
2.3.1.140 metabolism the enzyme catalyzes a step in the rosmarinic acid biosynthesis, pathway overview Melissa officinalis