1.14.14.15: (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] monooxygenase
This is an abbreviated version!
For detailed information about (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] monooxygenase, go to the full flat file.
Reaction
Synonyms
SgcC, SgcC3, SgcE6
ECTree
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Substrates Products
Substrates Products on EC 1.14.14.15 - (3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] monooxygenase
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REACTION DIAGRAM
(3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FADH2 + O2
(3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl-[peptidyl-carrier protein SgcC2] + FAD + H2O
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(R)-alpha-tyrosyl-[SgcC2] + FADH2 + O2
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SgcC3 can utilize both (S)- and (R)-alpha-tyrosyl-[SgcC2] but not 3-hydroxy-alpha-tyrosyl-[SgcC2] as a substrate
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(S)-alpha-tyrosyl-[SgcC2] + FADH2 + O2
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SgcC3 can utilize both (S)- and (R)-alpha-tyrosyl-[SgcC2] but not 3-hydroxy-alpha-tyrosyl-[SgcC2] as a substrate
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S-((3S)-3-amino-3-(3-bromo-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-bromo-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
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S-((3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
S-((3S)-3-amino-3-(3-fluoro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-fluoro-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
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?
S-((3S)-3-amino-3-(3-iodo-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-iodo-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
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S-((3S)-3-amino-3-(3-methyl-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-methyl-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
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?
S-((3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
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?
S-((3S)-3-amino-3-(3-chloro-4-hydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FADH2 + O2
S-((3S)-3-amino-3-(3-chloro-4,5-dihydroxyphenyl)propanoyl)-[peptidyl-carrier protein SgcC2] + FAD + H2O
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the enzyme is involved in the biosynthesis of the (S)-3-chloro-5-hydroxy-beta-tyrosine moiety prior to incorporation into the chromoprotein antitumor antibiotic C-1027. FADH2 is supplied by the C-1027 pathway-specific flavin reductase SgcE6
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no activity with [peptidyl-carrier-protein SgcC2]-beta-tyrosyl thioester and [peptidyl-carrier-protein SgcC2]-(S)-3-hydroxy-beta-tyrosyl thioester
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additional information
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SgcC3 also efficiently catalyzes bromination but not fluorination or iodination
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additional information
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no activity with 3-hydroxy-alpha-tyrosyl-S-SgcC2
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additional information
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subunit SgcE6 is responsible for the production of FADH2. FADH2 diffuses to SgcC, where Arg119 activates an O2 molecule to form a C-4a-hydroperoxyflavin intermediate. SgcC2 interacts with SgcC and guides the (S)-3-chloro-beta-tyrosyl moiety into the active site. It is activated by conserved general base His161, which results in electrophilic attack of the hydroxy group of the C-4a-hydroperoxyflavin intermediate, introducing a hydroxy group at the C-5 position of the (S)-3-chloro-beta-tyrosyl moiety. The hydroxyflavin (FADHO-) abstracts a proton from the C-5 atom of the intermediate, resulting in the formation of the rearomatizated (S)-3-chloro-5-hydroxy-beta-tyrosyl-S-SgcC2, which then dissociates from SgcC. Finally, the hydroxyflavin (FADHOH) undergoes dehydration to form FAD, which is released and recycled by SgcE6
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