DB code: D00411

CATH domain 3.40.47.10 : Peroxisomal Thiolase; Chain A, domain 1 Catalytic domain
3.40.47.10 : Peroxisomal Thiolase; Chain A, domain 1 Catalytic domain
E.C. 2.3.1.74
CSA 1cgk
M-CSA 1cgk
MACiE

CATH domain Related DB codes (homologues)
3.40.47.10 : Peroxisomal Thiolase; Chain A, domain 1 D00090 D00509 D00825 D00826 D00867 D00871

Uniprot Enzyme Name
UniprotKB Protein name Synonyms Pfam
P30074 Chalcone synthase 2
EC 2.3.1.74
Naringenin-chalcone synthase 2
PF02797 (Chal_sti_synt_C)
PF00195 (Chal_sti_synt_N)
[Graphical View]

KEGG enzyme name
naringenin-chalcone synthase
chalcone synthase
flavanone synthase
6'-deoxychalcone synthase
chalcone synthetase
DOCS
CHS

UniprotKB: Accession Number Entry name Activity Subunit Subcellular location Cofactor
P30074 CHS2_MEDSA 3 malonyl-CoA + 4-coumaroyl-CoA = 4 CoA + naringenin chalcone + 3 CO(2).

KEGG Pathways
Map code Pathways E.C.
MAP00941 Flavonoid biosynthesis

Compound table
Substrates Products Intermediates
KEGG-id C00083 C00223 C00010 C06561 C00011
E.C.
Compound Malonyl-CoA 4-Coumaroyl-CoA CoA Naringenin chalcone CO2 Monoketide intermediate Enolic acetyl-CoA Diketide CoA thioester Diketide intermediate Triketide CoA thioester Triketide intermediate Tetraketide CoA thioester Tetraketide intermediate Cyclized tetraketide
Type amine group,carbohydrate,carboxyl group,nucleotide ,peptide/protein,sulfide group amine group,aromatic ring (only carbon atom),carbohydrate,nucleotide ,peptide/protein,sulfide group amine group,carbohydrate,nucleotide ,peptide/protein,sulfhydryl group aromatic ring (only carbon atom),carbohydrate others
ChEBI 15531
85531
15346
15413
16526
PubChem 10663
644066
5280329
6440013
6816
87642
5280960
280
1bi5A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1bq6A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Bound:COA Unbound Unbound Unbound
1cgkA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Analogue:NAR Unbound Unbound
1cgzA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Analogue:STL Unbound Unbound
1chwA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1chwB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1cmlA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Analogue:MLC Unbound Unbound Unbound Unbound Intermediate-analogue:PIN
1d6fA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1d6hA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Bound:COA Unbound Unbound Unbound
1d6iA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1d6iB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i86A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i88A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i88B01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i89A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i89B01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i8bA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i8bB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1jwxA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0vA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0vB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0wA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Analogue:STL Unbound Unbound
1u0wB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Analogue:STL Unbound Unbound
1u0wC01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Analogue:STL Unbound Unbound
1u0wD01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Analogue:STL Unbound Unbound
1bi5A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1bq6A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1cgkA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1cgzA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1chwA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Analogue:HXC Unbound Unbound Unbound Unbound
1chwB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Analogue:HXC Unbound Unbound Unbound Unbound
1cmlA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1d6fA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1d6hA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1d6iA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1d6iB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i86A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i88A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i88B02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i89A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i89B02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i8bA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1i8bB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1jwxA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0vA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0vB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0wA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0wB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0wC02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound
1u0wD02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain Unbound Unbound Unbound Unbound Unbound Unbound

Reference for Active-site residues
resource references E.C.
PDB;1bi5, 1bq6, 1cgk, 1cgz, 1chw & Swiss-prot;P48391

Active-site residues
PDB Catalytic residues Cofactor-binding residues Modified residues Main-chain involved in catalysis Comment
1bi5A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1bq6A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1cgkA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain CYS 164;PHE 215
1cgzA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain CYS 164;PHE 215
1chwA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 mutant C164S
1chwB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 mutant C164S
1cmlA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 mutant C164A
1d6fA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 mutant C164A
1d6hA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1d6iA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1d6iB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1i86A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1i88A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1i88B01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1i89A01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1i89B01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1i8bA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1i8bB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;PHE 215 CSD 164(S-sulfinocysteine)
1jwxA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ; CSD 164(S-sulfinocysteine) mutant F215S
1u0vA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain CYS 164;PHE 215
1u0vB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain CYS 164;PHE 215
1u0wA01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain CYS 164;PHE 215
1u0wB01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain CYS 164;PHE 215
1u0wC01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain CYS 164;PHE 215
1u0wD01 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain CYS 164;PHE 215
1bi5A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1bq6A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1cgkA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1cgzA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1chwA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1chwB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1cmlA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1d6fA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1d6hA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303; mutant N336A
1d6iA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;ASN 336 mutant H303Q
1d6iB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain ;ASN 336 mutant H303Q
1i86A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1i88A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1i88B02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1i89A02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1i89B02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1i8bA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1i8bB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1jwxA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1u0vA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1u0vB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1u0wA02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1u0wB02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1u0wC02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336
1u0wD02 Pdbj logo s Rasmollogo id Rasmollogo chain Mmcif id Mmcif chain HIS 303;ASN 336

References for Catalytic Mechanism
References Sections No. of steps in catalysis
[5]
Fig.6, p.778-782 8
[6]
Fig.1, p.39642-39645 2
[7]
Fig.1, Fig.9, p.898-900 2
[9]
Fig.4, p.394-397 2
[11]
Fig.1, p.14836-14387 4
[14]
Fig.1, Fig.6, p.45169-45174
[15]
Fig.1, Fig.5, Fig.6

References
[1]
Resource
Comments
Medline ID
PubMed ID 6853502
Journal J Biol Chem
Year 1983
Volume 258
Pages 6730-4
Authors Schuz R, Heller W, Hahlbrock K
Title Substrate specificity of chalcone synthase from Petroselinum hortense. Formation of phloroglucinol derivatives from aliphatic substrates.
Related PDB
Related UniProtKB
[2]
Resource
Comments
Medline ID
PubMed ID 3777940
Journal Arch Biochem Biophys
Year 1986
Volume 250
Pages 364-72
Authors Knogge W, Schmelzer E, Weissenbock G
Title The role of chalcone synthase in the regulation of flavonoid biosynthesis in developing oat primary leaves.
Related PDB
Related UniProtKB
[3]
Resource
Comments
Medline ID
PubMed ID 7713888
Journal J Biol Chem
Year 1995
Volume 270
Pages 7922-8
Authors Tropf S, Karcher B, Schroder G, Schroder J
Title Reaction mechanisms of homodimeric plant polyketide synthase (stilbenes and chalcone synthase). A single active site for the condensing reaction is sufficient for synthesis of stilbenes, chalcones, and 6'-deoxychalcones.
Related PDB
Related UniProtKB
[4]
Resource
Comments
Medline ID
PubMed ID 10476972
Journal Nature
Year 1999
Volume 400
Pages 897-9
Authors Funa N, Ohnishi Y, Fujii I, Shibuya M, Ebizuka Y, Horinouchi S
Title A new pathway for polyketide synthesis in microorganisms.
Related PDB
Related UniProtKB
[5]
Resource
Comments X-ray crystallography
Medline ID
PubMed ID 10426957
Journal Nat Struct Biol
Year 1999
Volume 6
Pages 775-84
Authors Ferrer JL, Jez JM, Bowman ME, Dixon RA, Noel JP
Title Structure of chalcone synthase and the molecular basis of plant polyketide biosynthesis.
Related PDB 1bi5 1bq6 1cgk 1cgz 1chw 1cml
Related UniProtKB
[6]
Resource
Comments
Medline ID
PubMed ID 11006298
Journal J Biol Chem
Year 2000
Volume 275
Pages 39640-6
Authors Jez JM, Noel JP
Title Mechanism of chalcone synthase. pKa of the catalytic cysteine and the role of the conserved histidine in a plant polyketide synthase.
Related PDB
Related UniProtKB
[7]
Resource
Comments X-RAY CRYSTALLOGRAPHY (1.69 ANGSTROMS)
Medline ID 20120577
PubMed ID 10653632
Journal Biochemistry
Year 2000
Volume 39
Pages 890-902
Authors Jez JM, Ferrer JL, Bowman ME, Dixon RA, Noel JP
Title Dissection of malonyl-coenzyme A decarboxylation from polyketide formation in the reaction mechanism of a plant polyketide synthase.
Related PDB 1d6f 1d6h 1d6i
Related UniProtKB P30074
[8]
Resource
Comments
Medline ID
PubMed ID 10973790
Journal Biochem Biophys Res Commun
Year 2000
Volume 275
Pages 725-30
Authors Suh DY, Kagami J, Fukuma K, Sankawa U
Title Evidence for catalytic cysteine-histidine dyad in chalcone synthase.
Related PDB
Related UniProtKB
[9]
Resource
Comments
Medline ID
PubMed ID 11774005
Journal J Ind Microbiol Biotechnol
Year 2001
Volume 27
Pages 393-8
Authors Jez JM, Ferrer JL, Bowman ME, Austin MB, Schroder J, Dixon RA, Noel JP
Title Structure and mechanism of chalcone synthase-like polyketide synthases.
Related PDB
Related UniProtKB
[10]
Resource
Comments
Medline ID
PubMed ID 11728463
Journal FEBS Lett
Year 2001
Volume 508
Pages 413-7
Authors Lukacin R, Schreiner S, Matern U
Title Transformation of acridone synthase to chalcone synthase.
Related PDB
Related UniProtKB
[11]
Resource
Comments
Medline ID
PubMed ID 11732902
Journal Biochemistry
Year 2001
Volume 40
Pages 14829-38
Authors Jez JM, Bowman ME, Noel JP
Title Structure-guided programming of polyketide chain-length determination in chalcone synthase.
Related PDB 1i86 1i88 1i89 1i8b
Related UniProtKB
[12]
Resource
Comments
Medline ID
PubMed ID 11959984
Journal Proc Natl Acad Sci U S A
Year 2002
Volume 99
Pages 5319-24
Authors Jez JM, Bowman ME, Noel JP
Title Expanding the biosynthetic repertoire of plant type III polyketide synthases by altering starter molecule specificity.
Related PDB 1jwx
Related UniProtKB
[13]
Resource
Comments
Medline ID
PubMed ID 12502351
Journal J Nat Prod
Year 2002
Volume 65
Pages 1956-62
Authors Moore BS, Hertweck C, Hopke JN, Izumikawa M, Kalaitzis JA, Nilsen G, O'Hare T, Piel J, Shipley PR, Xiang L, Austin MB, Noel JP
Title Plant-like biosynthetic pathways in bacteria: from benzoic acid to chalcone.
Related PDB
Related UniProtKB
[14]
Resource
Comments
Medline ID
PubMed ID 15265863
Journal J Biol Chem
Year 2004
Volume 279
Pages 45162-74
Authors Austin MB, Izumikawa M, Bowman ME, Udwary DW, Ferrer JL, Moore BS, Noel JP
Title Crystal structure of a bacterial type III polyketide synthase and enzymatic control of reactive polyketide intermediates.
Related PDB
Related UniProtKB
[15]
Resource
Comments
Medline ID
PubMed ID 15380179
Journal Chem Biol
Year 2004
Volume 11
Pages 1179-94
Authors Austin MB, Bowman ME, Ferrer JL, Schroder J, Noel JP
Title An aldol switch discovered in stilbene synthases mediates cyclization specificity of type III polyketide synthases.
Related PDB 1u0v 1u0w
Related UniProtKB

Comments
According to the literature [5], this enzyme catalyzes the following reactions:
(A) Transfer of acyl group from sulfur atom of coumaronyl-CoA to the nucleophilic cysteine residue, forming monoketide intermediate:
(B) Eliminative double-bond formation; Elimination of CO2 from malonyl-CoA, giving enolic acetyl-CoA:
(C) Transfer of acyl group (monoketide) from the cysteine residue to the carbon atom of enolic acetyl-CoA, forming diketide CoA thioester:
(D) Transfer of acyl group (diketide) from sulfur atom of diketide CoA thioester to the cysteine residue, forming diketide intermediate:
(E) Eliminative double-bond formation; Elimination of CO2 from malonyl-CoA, giving enolic acetyl-CoA:
(F) Transfer of acyl group (diketide) from the cysteine residue to the carbon atom of enolic acetyl-CoA, forming triketide CoA thioester:
(G) Transfer of acyl group (triketide) from sulfur atom of triketide CoA thioester to the cysteine residue, forming triketide intermediate:
(H) Eliminative double-bond formation; Elimination of CO2 from malonyl-CoA, giving enolic acetyl-CoA:
(I) Transfer of acyl group (triketide) from the cysteine residue to the carbon atom of enolic acetyl-CoA, forming tetraketide CoA thioester:
(J) Transfer of acyl group (tetraketide) from sulfur atom of triketide CoA thioester to the cysteine residue, forming tetraketide intermediate:
(K) Intramolecular transfer of acyl group from the cysteine to the methylene carbon of the tetraketide intermediate (Cyclization):
(L) Isomerization of carbonyl oxygen to hydroxyl oxygen (Aromatization):

Created Updated
2002-11-25 2009-02-26