Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	1 proteins
Enzyme class ^help_outline	EC 1.14.14.15 (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] monooxygenase

Reaction participants Show >> << Hide

Name^help_outline (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[SgcC2 peptidyl-carrier protein] Identifier RHEA-COMP:9806 Reactive part ^help_outline
- Name ^help_outline (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl residue Identifier CHEBI:78297 Charge 1 Formula C9H10ClNO2 SMILES^help_outline [NH3+][C@@H](CC(-*)=O)c1ccc(O)c(Cl)c1 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 1 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline FADH₂ Identifier CHEBI:58307 Charge -2 Formula C27H33N9O15P2 InChIKey^help_outline YPZRHBJKEMOYQH-UYBVJOGSSA-L SMILES^help_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n3cnc4c(N)ncnc34)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 161 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline O₂ Identifier CHEBI:15379 (CAS: 7782-44-7) ^help_outline Charge 0 Formula O2 InChIKey^help_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILES^help_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline (3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl-[SgcC2 peptidyl-carrier protein] Identifier RHEA-COMP:9805 Reactive part ^help_outline
- Name ^help_outline (3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl residue Identifier CHEBI:78296 Charge 1 Formula C9H10ClNO3 SMILES^help_outline [NH3+][C@@H](CC(-*)=O)c1cc(O)c(O)c(Cl)c1 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 1 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline FAD Identifier CHEBI:57692 Charge -3 Formula C27H30N9O15P2 InChIKey^help_outline IMGVNJNCCGXBHD-UYBVJOGSSA-K SMILES^help_outline Cc1cc2nc3c(nc(=O)[n-]c3=O)n(C[C@H](O)[C@H](O)[C@H](O)COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n3cnc4c(N)ncnc34)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 170 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H₂O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) ^help_outline Charge 0 Formula H2O InChIKey^help_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILES^help_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:41560	RHEA:41561	RHEA:41562	RHEA:41563
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins	1 proteins
EC numbers ^help_outline	1.14.14.15
MetaCyc ^help_outline		RXN-15398

Publications

Characterization of the two-component, FAD-dependent monooxygenase SgcC that requires carrier protein-tethered substrates for the biosynthesis of the enediyne antitumor antibiotic C-1027.

Lin S., Van Lanen S.G., Shen B.

C-1027 is a potent antitumor antibiotic composed of an apoprotein (CagA) and a reactive enediyne chromophore. The chromophore has four distinct chemical moieties, including an ( S)-3-chloro-5-hydroxy-beta-tyrosine moiety, the biosynthesis of which from l-alpha-tyrosine requires five proteins: SgcC ... >> More

C-1027 is a potent antitumor antibiotic composed of an apoprotein (CagA) and a reactive enediyne chromophore. The chromophore has four distinct chemical moieties, including an ( S)-3-chloro-5-hydroxy-beta-tyrosine moiety, the biosynthesis of which from l-alpha-tyrosine requires five proteins: SgcC, SgcC1, SgcC2, SgcC3, and SgcC4; a sixth protein, SgcC5, catalyzes the incorporation of this beta-amino acid moiety into C-1027. Biochemical characterization of SgcC has now revealed that (i) SgcC is a two-component, flavin adenine dinucleotide (FAD)-dependent monooxygenase, (ii) SgcC is only active with SgcC2 (peptidyl carrier protein)-tethered substrates, (iii) SgcC-catalyzed hydroxylation requires O 2 and FADH 2, the latter supplied by the C-1027 pathway-specific flavin reductase SgcE6 or Escherichia coli flavin reductase Fre, and (iv) SgcC efficiently catalyzes regioselective hydroxylation of 3-substituted beta-tyrosyl-S-SgcC2 analogues, including the chloro-, bromo-, iodo-, fluoro-, and methyl-substituted analogues, but does not accept 3-hydroxy-beta-tyrosyl-S-SgcC2 as a substrate. Together with the in vitro data for SgcC4, SgcC1, and SgcC3, the results establish that SgcC catalyzes the hydroxylation of ( S)-3-chloro-beta-tyrosyl-S-SgcC2 as the final step in the biosynthesis of the ( S)-3-chloro-5-hydroxy-beta-tyrosine moiety prior to incorporation into C-1027. SgcC now represents the first biochemically characterized two-component, FAD-dependent monooxygenase that acts on a carrier-protein-tethered aromatic substrate. << Less

J. Am. Chem. Soc. 130:6616-6623(2008) [PubMed] [EuropePMC]

RHEA:41560 (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[SgcC2 peptidyl-carrier protein] + FADH2 + O2 = (3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl-[SgcC2 peptidyl-carrier protein] + FAD + H(+) + H2O

Enzymes

Reaction participants Show >> << Hide

Cross-references

Publications

Characterization of the two-component, FAD-dependent monooxygenase SgcC that requires carrier protein-tethered substrates for the biosynthesis of the enediyne antitumor antibiotic C-1027.