MetaCyc Enzyme: 5-pentadecatrienylresorcinol synthase

Gene: ARS1 Accession Number: G-11965 (MetaCyc)

Synonyms: Sb05g022500

Species: Sorghum bicolor

There are two functional genes in the sorghum genome encoding alkylresorcinol synthases, ARS1 and ARS2. ARS1 and ARS2 were heterologously expressed in Escherichia coli. In vitro enzyme assay of the recombinant proteins indicated that both proteins acted with the physiological substrates hexadecatrienoyl-CoA (C16:3Δ9,12,15) and malonyl-CoA. It is noteworthy that maximum in vitro enzyme activity was observed with myristoyl-CoA (C14:0) and palmitoleoyl-CoA (C16:1Δ9) for ARS1 and ARS2, respectively. Benzoyl-CoA, isovaleryl-CoA or isobutyryl-CoA could not replace malonyl-CoA in the condensation reaction.

A complete correlation between RNAi silencing of ARS1 or ARS2 with the reduction of sorgoleone accumulation level was found in transgenic RNAi plants, indicating the physiological role of ARS1 and ARS2 in sorgoleone biosynthesis.

Both ARS1 and ARS2 were found preferentially expressed in sorghum root hair cells, where sorgoleone is predominantly detected.

Citations: [Cook10]

Molecular Weight of Polypeptide: 43.0 kD (from nucleotide sequence)

Unification Links: String:4558.Sb05g022510.1 , UniProt:C5Y4Z2

Relationship Links: InterPro:IN-FAMILY:IPR001099 , InterPro:IN-FAMILY:IPR011141 , InterPro:IN-FAMILY:IPR012328 , InterPro:IN-FAMILY:IPR016038 , InterPro:IN-FAMILY:IPR016039 , Pfam:IN-FAMILY:PF00195 , Pfam:IN-FAMILY:PF02797

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Created 12-Apr-2010 by Zhang P , TAIR

Enzymatic reaction of: 5-pentadecatrienylresorcinol synthase

Synonyms: alkylresorcinol synthase

EC Number: 2.3.1.-

(9Z,12Z,15Z)-hexadeca-9,12,15-trienoyl-CoA + 3 malonyl-CoA + 3 H+ <=> 5-pentadecatrienyl resorcinol + 4 CO2 + 4 coenzyme A

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: sorgoleone biosynthesis


Cook10: Cook D, Rimando AM, Clemente TE, Schroder J, Dayan FE, Nanayakkara NP, Pan Z, Noonan BP, Fishbein M, Abe I, Duke SO, Baerson SR (2010). "Alkylresorcinol Synthases Expressed in Sorghum bicolor Root Hairs Play an Essential Role in the Biosynthesis of the Allelopathic Benzoquinone Sorgoleone." Plant Cell. PMID: 20348430

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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