KEGG ENZYME: 2.3.1.156

ENZYME: 2.3.1.156

Entry

EC 2.3.1.156                Enzyme

Name

phloroisovalerophenone synthase;
valerophenone synthase;
3-methyl-1-(trihydroxyphenyl)butan-1-one synthase;
acylphloroglucinol synthase;
isovaleryl-CoA:malonyl-CoA acyltransferase

Class

Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups

Sysname

acyl-CoA:malonyl-CoA acyltransferase

Reaction(IUBMB)

(1) isovaleryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisovalerophenone [RN:R05331];
(2) isobutyryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisobutyrophenone [RN:R11584]

Reaction(KEGG)

R05331 R11584

Substrate

isovaleryl-CoA [CPD:C02939];
malonyl-CoA [CPD:C00083];
isobutyryl-CoA [CPD:C00630]

Product

CoA [CPD:C00010];
CO2 [CPD:C00011];
phlorisovalerophenone [CPD:C07350];
phlorisobutyrophenone [CPD:C07351]

Comment

Closely related to EC 2.3.1.74, naringenin-chalcone synthase. Also acts on isobutyryl-CoA as substrate to give phlorisobutyrophenone. The products are intermediates in the biosynthesis of the bitter acids in hops (Humulus lupulus) and glucosides in strawberry (Fragaria X ananassa). It is also able to generate naringenin chalcone from 4-coumaroyl-CoA.

History

EC 2.3.1.156 created 2000

Reference

Authors

Fung SY, Zuurbier KWM, Paniego NB, Scheffer JJC, Verpoorte R.

Title

Enzymes from the biosynthesis of hop alpha and beta acids.

Journal

Proc 26th Congr Eur Brew Conv 215-221 (1997)

Reference

2 [PMID:9883590]

Authors

Zuurbier KW, Leser J, Berger T, Hofte AJ, Schroder G, Verpoorte R, Schroder J

Title

4-Hydroxy-2-pyrone formation by chalcone and stilbene synthase with nonphysiological substrates.

Journal

Phytochemistry 49:1945-51 (1998)
DOI:10.1016/S0031-9422(98)00346-X

Reference

3 [PMID:26169681]

Authors

Song C, Ring L, Hoffmann T, Huang FC, Slovin J, Schwab W

Title

Acylphloroglucinol Biosynthesis in Strawberry Fruit.

Journal

Plant Physiol 169:1656-70 (2015)
DOI:10.1104/pp.15.00794

Other DBs

ExplorEnz - The Enzyme Database:

2.3.1.156

IUBMB Enzyme Nomenclature:

2.3.1.156

ExPASy - ENZYME nomenclature database:

2.3.1.156

BRENDA, the Enzyme Database:

2.3.1.156

LinkDB

DBGET integrated database retrieval system