The Enzyme Database

Your query returned 10 entries.    printer_iconPrintable version



EC 1.3.1.57     
Accepted name: phloroglucinol reductase
Reaction: dihydrophloroglucinol + NADP+ = phloroglucinol + NADPH + H+
Glossary: phloroglucinol = 1,3,5-trihydroxybenzene
Systematic name: dihydrophloroglucinol:NADP+ oxidoreductase
Comments: Involved in the gallate anaerobic degradation pathway in bacteria.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, UM-BBD, CAS registry number: 80804-59-7
References:
1.  Haddock, J.D. and Ferry, J.G. Purification and properties of phloroglucinol reductase from Eubacterium oxidoreducens G-41. J. Biol. Chem. 264 (1989) 4423–4427. [PMID: 2925649]
[EC 1.3.1.57 created 2000]
 
 
EC 1.97.1.2     
Accepted name: pyrogallol hydroxytransferase
Reaction: 1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene = 1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
Other name(s): 1,2,3,5-tetrahydroxybenzene hydroxyltransferase; 1,2,3,5-tetrahydroxybenzene:pyrogallol transhydroxylase; 1,2,3,5-tetrahydroxybenzene-pyrogallol hydroxyltransferase (transhydroxylase); pyrogallol hydroxyltransferase; 1,2,3,5-tetrahydroxybenzene:1,2,3-trihydroxybenzene hydroxyltransferase
Systematic name: 1,2,3,5-tetrahydroxybenzene:1,2,3-trihydroxybenzene hydroxytransferase
Comments: 1,2,3,5-Tetrahydroxybenzene acts as a co-substrate for the conversion of pyrogallol into phloroglucinol, and for a number of similar isomerizations. The enzyme is provisionally listed here, but might be considered as the basis for a new class in the transferases, analogous to the aminotransferases.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, PDB, UM-BBD, CAS registry number: 176591-26-7
References:
1.  Brune, A. and Schink, B. Pyrogallol-to-phloroglucinol conversion and other hydroxyl-transfer reactions catalyzed by cell extracts of Pelobacter acidigallici. J. Bacteriol. 172 (1990) 1070–1076. [DOI] [PMID: 2298693]
[EC 1.97.1.2 created 1992]
 
 
EC 2.3.1.156     
Accepted name: phloroisovalerophenone synthase
Reaction: (1) isovaleryl-CoA + 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisovalerophenone
(2) isobutyryl-CoA+ 3 malonyl-CoA = 4 CoA + 3 CO2 + phlorisobutyrophenone
For diagram of polyketides biosynthesis, click here
Glossary: phlorisobutyrophenone = 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
phlorisovalerophenone = 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
Other name(s): valerophenone synthase; 3-methyl-1-(trihydroxyphenyl)butan-1-one synthase; acylphloroglucinol synthase; isovaleryl-CoA:malonyl-CoA acyltransferase
Systematic name: acyl-CoA:malonyl-CoA acyltransferase
Comments: 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.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Fung, S.Y., Zuurbier, K.W.M., Paniego, N.B., Scheffer, J.J.C. and Verpoorte, R. Enzymes from the biosynthesis of hop α and β acids. Proc. 26th Congr. Eur. Brew. Conv. (1997) 215–221.
2.  Zuurbier, K.W.M., Leser, J., Berger, T., Hofte, A.J.P., Schroder, G., Verpoorte, R. and Schroder, J. 4-Hydroxy-2-pyrone formation by chalcone and stilbene synthase with nonphysiological substrates. Phytochemistry 49 (1998) 1945–1951. [PMID: 9883590]
3.  Song, C., Ring, L., Hoffmann, T., Huang, F.C., Slovin, J. and Schwab, W. Acylphloroglucinol biosynthesis in strawberry fruit. Plant Physiol. 169 (2015) 1656–1670. [DOI] [PMID: 26169681]
[EC 2.3.1.156 created 2000]
 
 
EC 2.3.1.253     
Accepted name: phloroglucinol synthase
Reaction: 3 malonyl-CoA = phloroglucinol + 3 CO2 + 3 CoA
For diagram of polyketides biosynthesis, click here
Glossary: phloroglucinol = 1,3,5-trihydroxybenzene
Other name(s): phlD (gene name)
Systematic name: malonyl-CoA:malonyl-CoA malonyltransferase (decarboxylating, phloroglucinol-forming)
Comments: The enzyme, characterized from the bacterium Pseudomonas protegens Pf-5, is a type III polyketide synthase. The mechanism involves the cyclization of an activated 3,5-dioxoheptanedioate intermediate. The enzyme exhibits broad substrate specificity, and can accept C4-C12 aliphatic acyl-CoAs and phenylacetyl-CoA as the starter molecules, forming 6-(polyoxoalkyl)-α-pyrones by sequential condensation with malonyl-CoA.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Achkar, J., Xian, M., Zhao, H. and Frost, J.W. Biosynthesis of phloroglucinol. J. Am. Chem. Soc. 127 (2005) 5332–5333. [PMID: 15826166]
2.  Zha, W., Rubin-Pitel, S.B. and Zhao, H. Characterization of the substrate specificity of PhlD, a type III polyketide synthase from Pseudomonas fluorescens. J. Biol. Chem. 281 (2006) 32036–32047. [DOI] [PMID: 16931521]
[EC 2.3.1.253 created 2016]
 
 
EC 2.3.1.272     
Accepted name: 2-acetylphloroglucinol acetyltransferase
Reaction: 2 2-acetylphloroglucinol = 2,4-diacetylphloroglucinol + phloroglucinol
Glossary: phloroglucinol = benzene-1,3,5-triol
Other name(s): MAPG ATase
Systematic name: 2-acetylphloroglucinol C-acetyltransferase
Comments: The enzyme from the bacterium Pseudomonas sp. YGJ3 is composed of three subunits named PhlA, PhlB and PhlC. Production of 2,4-diacetylphloroglucinol, which has antibiotic activity, is strongly inhibited by chloride ions.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Hayashi, A., Saitou, H., Mori, T., Matano, I., Sugisaki, H. and Maruyama, K. Molecular and catalytic properties of monoacetylphloroglucinol acetyltransferase from Pseudomonas sp. YGJ3. Biosci. Biotechnol. Biochem. 76 (2012) 559–566. [DOI] [PMID: 22451400]
[EC 2.3.1.272 created 2018]
 
 
EC 2.4.1.358     
Accepted name: acylphloroglucinol glucosyltransferase
Reaction: UDP-α-D-glucose + 2-acylphloroglucinol = UDP + 2-acylphloroglucinol 1-O-β-D-glucoside
Glossary: phlorisobutyrophenone = 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one
phlorisovalerophenone = 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
Other name(s): UGT71K3
Systematic name: UDP-α-D-glucose:2-acylphloroglucinol 1-O-β-glucosyltransferase
Comments: Isolated from strawberries (Fragaria X ananassa). Acts best on phloroisovalerophenone and phlorobutyrophenone but will also glycosylate many other phenolic compounds. A minor product of the reaction is the 5-O-β-D-glucoside.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Song, C., Zhao, S., Hong, X., Liu, J., Schulenburg, K. and Schwab, W. A UDP-glucosyltransferase functions in both acylphloroglucinol glucoside and anthocyanin biosynthesis in strawberry (Fragaria x ananassa). Plant J. 85 (2016) 730–742. [PMID: 26859691]
[EC 2.4.1.358 created 2018]
 
 
EC 2.5.1.136     
Accepted name: 2-acylphloroglucinol 4-prenyltransferase
Reaction: dimethylallyl diphosphate + a 2-acylphloroglucinol = diphosphate + a 2-acyl-4-prenylphloroglucinol
Glossary: naringenin chalcone = 2′,4,4′,6′-tetrahydroxychalcone = 3-(4-hydroxyphemyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
phlorisovalerophenone = 3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
Other name(s): PT-1 (gene name); PT1L (gene name); aromatic prenyltransferase (ambiguous)
Systematic name: dimethylallyl diphosphate:2-acylphloroglucinol 4-dimethylallyltransferase
Comments: The enzyme, characterized from hop (Humulus lupulus), acts on phlorisovalerophenone, phlormethylbutanophenone, and phlorisobutanophenone during the synthesis of bitter acids. It also acts with much lower activity on naringenin chalcone. Forms a complex with EC 2.5.1.137, 2-acyl-4-prenylphloroglucinol 6-prenyltransferase, which catalyses additional prenylation reactions. Requires Mg2+.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Tsurumaru, Y., Sasaki, K., Miyawaki, T., Uto, Y., Momma, T., Umemoto, N., Momose, M. and Yazaki, K. HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops. Biochem. Biophys. Res. Commun. 417 (2012) 393–398. [DOI] [PMID: 22166201]
2.  Li, H., Ban, Z., Qin, H., Ma, L., King, A.J. and Wang, G. A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter acid pathway. Plant Physiol. 167 (2015) 650–659. [DOI] [PMID: 25564559]
[EC 2.5.1.136 created 2017]
 
 
EC 2.5.1.137     
Accepted name: 2-acyl-4-prenylphloroglucinol 6-prenyltransferase
Reaction: (1) dimethylallyl diphosphate + a 2-acyl-4-prenylphloroglucinol = diphosphate + a 2-acyl-4,6-bisprenylphloroglucinol
(2) dimethylallyl diphosphate + a 2-acyl-4,6-bisprenylphloroglucinol = diphosphate + a 2-acyl-4,6,6-trisprenylcyclohexa-2,4-dien-1-one
Glossary: a 2-acyl-4,6,6-trisprenylcyclohexa-2,4-dien-1-one = a β bitter acid
Other name(s): PT2 (gene name); aromatic prenyltransferase (ambiguous)
Systematic name: dimethylallyl diphosphate:2-acyl-4-prenylphloroglucinol 6-dimethylallyltransferase
Comments: The enzyme, characterized from hop (Humulus lupulus), catalyses two successive prenylations of a 2-acyl-4-prenylphloroglucinol during the synthesis of bitter acids. Forms a complex with EC 2.5.1.136, 2-acylphloroglucinol 4-prenyltransferase, which catalyses the initial prenylation of the substrates. Requires Mg2+.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Li, H., Ban, Z., Qin, H., Ma, L., King, A.J. and Wang, G. A heteromeric membrane-bound prenyltransferase complex from hop catalyzes three sequential aromatic prenylations in the bitter acid pathway. Plant Physiol. 167 (2015) 650–659. [DOI] [PMID: 25564559]
[EC 2.5.1.137 created 2017]
 
 
EC 3.7.1.4     
Accepted name: phloretin hydrolase
Reaction: phloretin + H2O = phloretate + phloroglucinol
For diagram of phloretin biosynthesis, click here
Glossary: phloretin = 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
phloretate = 3-(4-hydroxyphenyl)propanoate
phloroglucinol = benzene-1,3,5-triol
Other name(s): ErPhy; lactase-phlorerin hydrolase; C-acylphenol hydrolase; 2′,4,4′,6′-tetrahydroxydehydrochalcone 1,3,5-trihydroxybenzenehydrolase (incorrect)
Systematic name: phloretin acylhydrolase (phloroglucinol forming)
Comments: Also hydrolyses other C-acylated phenols related to phloretin. Isolated from the fungus Aspergillus niger and the bacteria Pantoea agglomerans and Eubacterium ramulus.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 37289-38-6
References:
1.  Chatterjee, A.K. and Gibbins, L.N. Metabolism of phloridzin by Erwinia herbicola: nature of the degradation products, and the purification and properties of phloretin hydrolase. J. Bacteriol. 100 (1969) 594–600. [PMID: 5354935]
2.  Minamikawa, T., Jayasankar, N.P., Bohm, B.A., Taylor, I.E. and Towers, G.H. An inducible hydrolase from Aspergillus niger, acting on carbon-carbon bonds, for phlorrhizin and other C-acylated phenols. Biochem. J. 116 (1970) 889–897. [PMID: 5441377]
3.  Schoefer, L., Braune, A. and Blaut, M. Cloning and expression of a phloretin hydrolase gene from Eubacterium ramulus and characterization of the recombinant enzyme. Appl. Environ. Microbiol. 70 (2004) 6131–6137. [DOI] [PMID: 15466559]
[EC 3.7.1.4 created 1972, modified 2018]
 
 
EC 3.7.1.24     
Accepted name: 2,4-diacetylphloroglucinol hydrolase
Reaction: 2,4-diacetylphloroglucinol + H2O = 2-acetylphloroglucinol + acetate
Glossary: phloroglucinol = benzene-1,3,5-triol
2,4-diacetylphloroglucinol = 1,1′-(2,4,6-trihydroxybenzene-1,3-diyl)diethan-1-one
Other name(s): PhlG
Systematic name: 2,4-diacetylphloroglucinol acetylhydrolase
Comments: Requires Zn2+. Isolated from the bacteria Pseudomonas fluorescens, Pseudomonas sp. YGJ3 and Mycobacterium abscessus 103. It reduces the antibiotic activity of 2,4-diacetylphloroglucinol.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Bottiglieri, M. and Keel, C. Characterization of PhlG, a hydrolase that specifically degrades the antifungal compound 2,4-diacetylphloroglucinol in the biocontrol agent Pseudomonas fluorescens CHA0. Appl. Environ. Microbiol. 72 (2006) 418–427. [PMID: 16391073]
2.  He, Y.X., Huang, L., Xue, Y., Fei, X., Teng, Y.B., Rubin-Pitel, S.B., Zhao, H. and Zhou, C.Z. Crystal structure and computational analyses provide insights into the catalytic mechanism of 2,4-diacetylphloroglucinol hydrolase PhlG from Pseudomonas fluorescens. J. Biol. Chem. 285 (2010) 4603–4611. [PMID: 20018877]
3.  Saitou, H., Watanabe, M. and Maruyama, K. Molecular and catalytic properties of 2,4-diacetylphloroglucinol hydrolase (PhlG) from Pseudomonas sp. YGJ3. Biosci. Biotechnol. Biochem. 76 (2012) 1239–1241. [PMID: 22790955]
4.  Zhang, Z., Jiang, Y.L., Wu, Y. and He, Y.X. Crystallization and preliminary X-ray diffraction analysis of a putative carbon-carbon bond hydrolase from Mycobacterium abscessus 103. Acta Crystallogr. F Struct. Biol. Commun. 71 (2015) 239–242. [PMID: 25664803]
[EC 3.7.1.24 created 2019]
 
 


Data © 2001–2020 IUBMB
Web site © 2005–2020 Andrew McDonald