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3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3E)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
3-[(4S)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3E)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3E)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
nonenzymatic isomerization gives (3E)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate and (3Z)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate in the ration 50:1. Isomerization by BacB gives a 3:1 mixture of the E- and Z-isomers
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-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3E)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-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
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3E)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
nonenzymatic isomerization gives (3E)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate and (3Z)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate in the ration 50:1. Isomerization by BacB gives a 3:1 mixture of the E- and Z-isomers
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3E)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-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
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
-
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
the enzyme from the bacterium Bacillus subtilis is involved in the biosynthesis of the nonproteinogenic amino acid tetrahydrotyrosine a component of the dipeptide antibiotic bacilysin
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-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
3-[(4S)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate also undergoes a nonenzymatic isomerization
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-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
nonenzymatic isomerization gives (3E)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate and (3Z)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate in the ratio 50:1. Isomerization by BacB gives a 3:1 mixture of the E- and Z-isomers
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-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
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
the enzyme from the bacterium Bacillus subtilis is involved in the biosynthesis of the nonproteinogenic amino acid tetrahydrotyrosine a component of the dipeptide antibiotic bacilysin
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
3-[(4S)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate also undergoes a nonenzymatic isomerization
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
nonenzymatic isomerization gives (3E)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate and (3Z)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate in the ratio 50:1. Isomerization by BacB gives a 3:1 mixture of the E- and Z-isomers
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-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
-
-
?
3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3Z)-3-[(4R)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
-
-
-
?
3-[(4S)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3E)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
-
-
-
?
3-[(4S)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
(3E)-3-[(4S)-4-hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
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-
-
?
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Rajavel, M.; Gopal, B.
Analysis of multiple crystal forms of Bacillus subtilis BacB suggests a role for a metal ion as a nucleant for crystallization
Acta Crystallogr. Sect. D
66
635-639
2010
Bacillus subtilis (P39639), Bacillus subtilis 168 (P39639)
brenda
Wu, L.; Wu, H.; Chen, L.; Xie, S.; Zang, H.; Borriss, R.; Gao, X.
Bacilysin from Bacillus amyloliquefaciens FZB42 has specific bactericidal activity against harmful algal bloom species
Appl. Environ. Microbiol.
80
7512-7520
2014
Bacillus amyloliquefaciens (Q8KWT1)
brenda
Mahlstedt, S.A.; Walsh, C.T.
Investigation of anticapsin biosynthesis reveals a four-enzyme pathway to tetrahydrotyrosine in Bacillus subtilis
Biochemistry
49
912-923
2010
Bacillus subtilis (P39639), Bacillus subtilis 168 (P39639)
brenda
Parker, J.B., Walsh, C.T.
Olefin isomerization regiochemistries during tandem action of BacA and BacB on prephenate in bacilysin biosynthesis
Biochemistry
51
3241-3251
2012
Bacillus subtilis (P39639), Bacillus subtilis 168 (P39639)
brenda
Parker, J.B.; Walsh, C.T.
Stereochemical outcome at four stereogenic centers during conversion of prephenate to tetrahydrotyrosine by BacABGF in the bacilysin pathway
Biochemistry
51
5622-5632
2012
Bacillus subtilis (P39639), Bacillus subtilis 168 (P39639)
brenda
Rajavel, M.; Mitra, A.; Gopal, B.
Role of Bacillus subtilis BacB in the synthesis of bacilysin
J. Biol. Chem.
284
31882-31892
2009
Bacillus subtilis, Bacillus subtilis (P39639), Bacillus subtilis 168 (P39639)
brenda
5.3.3.19 3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate isomerase
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