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Literature summary for 6.3.2.49 extracted from

  • Parker, J.B.; Walsh, C.T.
    Action and timing of BacC and BacD in the late stages of biosynthesis of the dipeptide antibiotic bacilysin (2013), Biochemistry, 52, 889-901.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 6.3.2.49

Cloned(Commentary)

Cloned (Comment) Organism
overexpression in Escherichia coli with an N-terminal His6tag Bacillus subtilis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ATP + L-alanine + (1R,2S,6R)-anticapsin Bacillus subtilis the enzyme is involved in the biosynthesis of the dipeptide antibiotic bacilysin ADP + phosphate + bacilysin i.e. L-alanyl-3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-L-alanine ?
ATP + L-alanine + (1R,2S,6R)-anticapsin Bacillus subtilis 168 the enzyme is involved in the biosynthesis of the dipeptide antibiotic bacilysin ADP + phosphate + bacilysin i.e. L-alanyl-3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-L-alanine ?

Organism

Organism UniProt Comment Textmining
Bacillus subtilis P39641
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Bacillus subtilis 168 P39641
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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.
ATP + L-alanine + (1R,2S,5R,6S)-dihydroanticapsin
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 Bacillus subtilis ADP + phosphate + dihydrobacilysin
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 ?
ATP + L-alanine + (1R,2S,5R,6S)-dihydroanticapsin
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 Bacillus subtilis 168 ADP + phosphate + dihydrobacilysin
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 ?
ATP + L-alanine + (1R,2S,6R)-anticapsin the enzyme is involved in the biosynthesis of the dipeptide antibiotic bacilysin Bacillus subtilis ADP + phosphate + bacilysin i.e. L-alanyl-3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-L-alanine ?
ATP + L-alanine + (1R,2S,6R)-anticapsin when the DELTAbacC extract is exposed to the enzyme (BacD) and the dihydroanticapsin:NAD+ 7-oxidoreductase (BacC) the C7-hydroxyl of hydroanticapsin is oxidized to generate anticapsin. (1R,2S,6R)-anticapsin i.e. 3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-L-alanine Bacillus subtilis ADP + phosphate + bacilysin i.e. L-alanyl-3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-L-alanine ?
ATP + L-alanine + (1R,2S,6R)-anticapsin the enzyme is involved in the biosynthesis of the dipeptide antibiotic bacilysin Bacillus subtilis 168 ADP + phosphate + bacilysin i.e. L-alanyl-3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-L-alanine ?
ATP + L-alanine + (1R,2S,6R)-anticapsin when the DELTAbacC extract is exposed to the enzyme (BacD) and the dihydroanticapsin:NAD+ 7-oxidoreductase (BacC) the C7-hydroxyl of hydroanticapsin is oxidized to generate anticapsin. (1R,2S,6R)-anticapsin i.e. 3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-L-alanine Bacillus subtilis 168 ADP + phosphate + bacilysin i.e. L-alanyl-3-[(1R,2S,6R)-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl]-L-alanine ?
ATP + L-alanine + 3-[(1S)-4-oxocyclohex-2-en-1-yl]-L-alanine 3-[(1S)-4-oxocyclohex-2-en-1-yl]-L-alanine is a surrogate substrate for the enzyme, because currently there is no route for purifying dihydroanticapsin (with the epoxide intact) from DELTAbacC strain extracts. A simultaneous incubation of the enzyme (ligase BacD) with oxidoreductase BaC, (2S,4S,7R)-tetrahydrotyrosine, NAD+, L-Ala, and ATP yields the dipeptide product L-Ala-2S,4S-cyclohexenoyl-Ala. This result indicates the BacD ligase can intercept the nascent 4S-cyclohexenonyl-Ala and ligate its N-terminus to L-Ala before its free amino group undergoes intramolecular addition Bacillus subtilis ADP + phosphate + L-alanyl-[3-[(1S)-4-oxocyclohex-2-en-1-yl]-L-alanine]
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 ?
ATP + L-alanine + 3-[(1S)-4-oxocyclohex-2-en-1-yl]-L-alanine 3-[(1S)-4-oxocyclohex-2-en-1-yl]-L-alanine is a surrogate substrate for the enzyme, because currently there is no route for purifying dihydroanticapsin (with the epoxide intact) from DELTAbacC strain extracts. A simultaneous incubation of the enzyme (ligase BacD) with oxidoreductase BaC, (2S,4S,7R)-tetrahydrotyrosine, NAD+, L-Ala, and ATP yields the dipeptide product L-Ala-2S,4S-cyclohexenoyl-Ala. This result indicates the BacD ligase can intercept the nascent 4S-cyclohexenonyl-Ala and ligate its N-terminus to L-Ala before its free amino group undergoes intramolecular addition Bacillus subtilis 168 ADP + phosphate + L-alanyl-[3-[(1S)-4-oxocyclohex-2-en-1-yl]-L-alanine]
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 ?

Synonyms

Synonyms Comment Organism
alanine-anticapsin ligase
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 Bacillus subtilis
BacD
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 Bacillus subtilis
BSU37710 locus name Bacillus subtilis
L-Ala-L-aniticapsin ligase
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 Bacillus subtilis
L-alanine-L-aniticapsin ligase
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 Bacillus subtilis
YwfE
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 Bacillus subtilis