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Literature summary for 5.3.3.19 extracted from

  • Parker, J.B.; Walsh, C.T.
    Stereochemical outcome at four stereogenic centers during conversion of prephenate to tetrahydrotyrosine by BacABGF in the bacilysin pathway (2012), Biochemistry, 51, 5622-5632.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
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Bacillus subtilis

Inhibitors

Inhibitors Comment Organism Structure
additional information formation of the the 3Z isomer is severely inhibited by high concentrations of salt (above 250 mM) Bacillus subtilis

Organism

Organism UniProt Comment Textmining
Bacillus subtilis P39639
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Bacillus subtilis 168 P39639
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-

Purification (Commentary)

Purification (Comment) Organism
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Bacillus subtilis

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate the enzyme generates a mixture of 3E- and 3Z-isomers. It equilibrates the more stable 3E and less stable 3Z geometric isomers to give up to 25% of the 3Z isomer, which on subsequent reduction by BacG gives the desired 4S stereochemistry of the cyclohexanol scaffold Bacillus subtilis (3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
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?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate the enzyme generates a mixture of 3E- and 3Z-isomers. It equilibrates the more stable 3E and less stable 3Z geometric isomers to give up to 25% of the 3Z isomer, which on subsequent reduction by BacG gives the desired 4S stereochemistry of the cyclohexanol scaffold Bacillus subtilis 168 (3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate the enzyme generates a mixture of 3E- and 3Z-isomers. It equilibrates the more stable 3E and less stable 3Z geometric isomers to give up to 25% of the 3Z isomer, which on subsequent reduction by BacG gives the desired 4S stereochemistry of the cyclohexanol scaffold Bacillus subtilis (3E)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate the enzyme generates a mixture of 3E- and 3Z-isomers. It equilibrates the more stable 3E and less stable 3Z geometric isomers to give up to 25% of the 3Z isomer, which on subsequent reduction by BacG gives the desired 4S stereochemistry of the cyclohexanol scaffold Bacillus subtilis 168 (3E)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
-
?