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Information on EC 2.3.1.65 - bile acid-CoA:amino acid N-acyltransferase
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EC Tree
2.3.1.65 bile acid-CoA:amino acid N-acyltransferaseIUBMB Comments
Also acts on CoA derivatives of other bile acids. Taurine and 2-fluoro-beta-alanine can act as substrates, but more slowly . The enzyme can also conjugate fatty acids to glycine and can act as a very-long-chain acyl-CoA thioesterase . Bile-acid---amino-acid conjugates serve as detergents in the gastrointestinal tract, solubilizing long chain fatty acids, mono- and diglycerides, fat-soluble vitamins and cholesterol . This is the second enzyme in a two-step process leading to the conjugation of bile acids with amino acids; the first step is the conversion of bile acids into their acyl-CoA thioesters, which is catalysed by EC 6.2.1.7, cholate---CoA ligase.
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Word Map
- 2.3.1.65
- peroxisomal
-
unconjugated
- acyl-coas
-
thioesterases
- cholyl-coa
-
acid-conjugating
-
hbats
- gallbladder
- proliferator
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
bile acid-coa:amino acid n-acyltransferase, bacat, bile acid coa:amino acid n-acyltransferase, bile acid coa amino acid n-acyltransferase, baatp1, bile acid coenzyme a-amino acid n-acyltransferase, bile acid coenzyme a:amino acid n-acyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
acyltransferase, glycine-taurine N-
-
-
-
-
amino acid N-choloyltransferase
-
-
-
-
BAAT
BAATP1
BACAT
BAT
bile acid coenzyme A: amino acid N-acyltransferase
bile acidcoenzyme A:amino acid N-acyltransferase
glycine-taurine N-acyltransferase
-
-
-
-
hBAT
BAT
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
choloyl-CoA + glycine = CoA + glycocholate
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
-
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SYSTEMATIC NAME
IUBMB Comments
choloyl-CoA:glycine N-choloyltransferase
Also acts on CoA derivatives of other bile acids. Taurine and 2-fluoro-beta-alanine can act as substrates, but more slowly [4]. The enzyme can also conjugate fatty acids to glycine and can act as a very-long-chain acyl-CoA thioesterase [7]. Bile-acid---amino-acid conjugates serve as detergents in the gastrointestinal tract, solubilizing long chain fatty acids, mono- and diglycerides, fat-soluble vitamins and cholesterol [4]. This is the second enzyme in a two-step process leading to the conjugation of bile acids with amino acids; the first step is the conversion of bile acids into their acyl-CoA thioesters, which is catalysed by EC 6.2.1.7, cholate---CoA ligase.
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CAS REGISTRY NUMBER
COMMENTARY
74506-32-4
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
choloyl-CoA + 2-fluoro-beta-alanine
CoA + 2-fluoro-beta-alanylcholate
-
2-fluoro-beta-alanine is an excellent substrate like taurine
-
-
?
choloyl-CoA + D-alpha-alanine
CoA + D-alpha-alanylcholate
-
about 10% of the rate with glycine
-
-
?
deoxycholoyl-CoA + aminomethanesulfonate
CoA + aminomethanesulfonyldeoxycholate
-
-
-
-
?
ursodeoxycholoyl-CoA + glycine
CoA + glycoursodeoxycholate
-
24.8% of activity with choloyl-CoA
-
-
?
ursodeoxycholoyl-CoA + taurine
CoA + tauroursodeoxycholate
-
35.3% of activity with choloyl-CoA
-
-
?
chenodeoxycholoyl-CoA + glycine
CoA + glycochenodeoxycholate
-
rate of conjugation in decreasing order: deoxycholyl-CoA, cholyl-CoA, lithocholyl-CoA, chenodeoxycholyl-CoA
-
-
?
chenodeoxycholoyl-CoA + glycine
CoA + glycochenodeoxycholate
-
91.4% of activity with choloyl-CoA
-
-
?
chenodeoxycholoyl-CoA + glycine
CoA + glycochenodeoxycholate
-
glycine is a slightly better substrate than taurine, thioesterase activity in absence of glycine is about 20% of the conjugation activity
-
-
?
chenodeoxycholoyl-CoA + taurine
CoA + taurochenodeoxycholate
-
101.4% of activity with choloyl-CoA
-
-
?
choloyl-CoA + beta-alanine
CoA + beta-alanylcholate
-
beta-alanine is a poor substrate
-
-
?
choloyl-CoA + beta-alanine
CoA + beta-alanylcholate
-
about 10% of the rate with glycine
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
rate of conjugation in decreasing order: deoxycholyl-CoA, cholyl-CoA, lithocholyl-CoA, chenodeoxycholyl-CoA
-
ir
choloyl-CoA + glycine
CoA + glycocholate
-
conjugation of bile acids in the liver with glycine or taurine prior to being secreted into the bile duct
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
taurine can replace glycine, involved in conjugation of bile acids
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
ratio of glycine-/taurine-dependent activity is 1.0-1.4
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
conjugation of bile acids with glycine or taurine favors their excretion into bile and uptake from portal blood into the liver, it promotes absorption of fat and fat-soluble vitamins in the acidic environment of the small intestine by lowering the pKa of the bile acids and hence maintaining its solubility
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
taurine can replace glycine, involved in conjugation of bile acids
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
cholesterol degradation, glycine conjugates of bile acids occur in adult
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
glycine is a slightly better substrate than taurine, thioesterase activity in absence of glycine is about 20% of the conjugation activity
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
produces taurine- but little glycine-conjugated bile acid at physiological concentrations of glycine and taurine, dietary manipulations modify the glycine:taurine ratio
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
conjugation of bile acids in the liver with glycine or taurine prior to being secreted into the bile duct
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine can replace glycine, involved in conjugation of bile acids
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
synthesizes only taurine but no gylcine conjugates
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
conjugation of the CoA adducts of bile acids with taurine
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
ratio of glycine-/taurine-dependent activity is 1.0-1.4
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine is an excellent substrate
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
conjugation of bile acids with glycine or taurine favors their excretion into bile and uptake from portal blood into the liver, it promotes absorption of fat and fat-soluble vitamins in the acidic environment of the small intestine by lowering the pKa of the bile acids and hence maintaining its solubility
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine can replace glycine, involved in conjugation of bile acids
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
cholesterol degradation, bile acids are secreted as taurine conjugates in fetus and neonatus
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine-specific enzyme, no use of glycine or fluoro-beta-alanine as substrates
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine-specific enzyme, gallbladder bile contains only taurine conjugates of bile acids, bile acid conjugates increases their detergent properties, prevents their precipitation in the acidic milieu of the upper small intestine, in intestines they are responsible for the solubilization and absorption of fats, vitamins and fat-soluble compounds
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
produces taurine- but little glycine-conjugated bile acid at physiological concentrations of glycine and taurine, dietary manipulations modify the hepatic taurine concentration and glycine:taurine ratio
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine conjugates predominate in rat bile at normal hepatocellular concentrations of glycine and taurine
-
-
?
deoxycholoyl-CoA + glycine
CoA + glycodeoxycholate
-
rate of conjugation in decreasing order: deoxycholyl-CoA, cholyl-CoA, lithocholyl-CoA, chenodeoxycholyl-CoA
-
-
?
deoxycholoyl-CoA + glycine
CoA + glycodeoxycholate
-
92.4% of activity with choloyl-CoA
-
-
?
deoxycholoyl-CoA + taurine
CoA + taurodeoxycholate
-
81.7% of activity with choloyl-CoA
-
-
?
lithocholoyl-CoA + glycine
CoA + glycolithocholate
-
rate of conjugation in decreasing order: deoxycholyl-CoA, cholyl-CoA, lithocholyl-CoA, chenodeoxycholyl-CoA
-
-
?
lithocholoyl-CoA + glycine
CoA + glycolithocholate
-
58.4% of activity with choloyl-CoA
-
-
?
lithocholoyl-CoA + taurine
CoA + taurolithocholate
-
43% of activity with choloyl-CoA
-
-
?
additional information
?
-
-
not as acyl-CoA donors: acetyl-CoA, phenylacetyl-CoA and benzoyl-CoA
-
-
?
additional information
?
-
-
in absence of amino acid substrate choloyl-CoA is cleaved with the release of CoA and formation of a covalent cholate-enzyme complex
-
-
?
additional information
?
-
-
not: L-alpha-alanine, DL-cysteic acid, 4-aminobutyric acid, cysteine, sulfanilic acid
-
-
?
additional information
?
-
-
essential catalytic triad consisting of Cys-235, His-362 and Asp-328 with Cys-235 serving as the probable nucleophile and thus the site of covalent attachment of the bile acid molecule
-
-
?
additional information
?
-
-
may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids
-
-
?
additional information
?
-
-
in addition to its bile acid conjugating activity, the enzyme also possesses thioesterase and glycine conjugating activities with long- and very long-chain acyl-CoAs, at least in vitro. The enzyme can also hydrolyze long- and very-long-chain saturated acyl-CoAs (mainly C16:0-C26:0), the enzyme also conjugates fatty acids to glycine
-
-
?
additional information
?
-
-
bile acidcoenzyme A:amino acid N-acyltransferase is the sole enzyme responsible for conjugation of primary and secondary bile acids to taurine and glycine
-
-
?
additional information
?
-
-
identification of three novel single nucleotide polymorphisms, 147C>T in exon 2 (silent), 602G>C in exon 3 (Arg201Pro), and 1134C>T in exon 4 (silent), in the gene of bile acid CoA: amino acid N-acyltransferase. The allelic frequencies are 0.005 for 147C>T, 0.095 for 602G>C, and 0.015 for 1134C>T. The two known SNPs, 59G>A (Arg20Gln, rs1572983) and UTR1513G>A (rs2229594), are detected at a frequency of 0.500 and 0.425, respectively. In the haplotype analysis for the 59G>A and 602G>C polymorphisms, the allelic frequency of 59G-602G, 59G-602C, 59A-602G and 59A-602C is 0.405, 0.095, 0.500 and 0.000, respectively. The allelic frequency of the nonsynonymous SNP 602G>C is 0.194 in a Caucasian population
-
-
?
additional information
?
-
-
Cys-234 may be involved in the formation of a bile acid thioester at the active site
-
-
?
additional information
?
-
-
may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids
-
-
?
additional information
?
-
-
not: D-alanine, L-arginine, L-lysine, 2-hydroxyethanesulfonate, 2-aminoethanesulfonate, 1-aminoethanephosphonate and 2-aminoethanephosphonate, 3-aminopropanesulfonate
-
-
?
additional information
?
-
-
not as acyl-CoA donors: acetyl-CoA, phenylacetyl-CoA and benzoyl-CoA
-
-
?
additional information
?
-
-
not as acyl-CoA donors: succinoyl-CoA, palmitoyl-CoA
-
-
?
additional information
?
-
-
not: L-alpha-alanine, L-glutamine, L-ornithine
-
-
?
additional information
?
-
-
bile acid-coenzyme A:amino acid N-acyltransferase is the sole enzyme responsible for conjugation of primary and secondary bile acids to taurine and glycine
-
-
?
additional information
?
-
-
suppression of rBAT occurs at the transcriptional level, and the decrease in retinoid-X receptorY-alpha by septic insult may play a critical role in rBAT suppression at the early stage of polymicrobial sepsis
-
-
?
additional information
?
-
-
the enzyme improves the survival rate of rats and increases the bile acid concentrations in in septic livers
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
choloyl-CoA + glycine
CoA + glycocholate
-
conjugation of bile acids in the liver with glycine or taurine prior to being secreted into the bile duct
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
taurine can replace glycine, involved in conjugation of bile acids
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
conjugation of bile acids with glycine or taurine favors their excretion into bile and uptake from portal blood into the liver, it promotes absorption of fat and fat-soluble vitamins in the acidic environment of the small intestine by lowering the pKa of the bile acids and hence maintaining its solubility
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
taurine can replace glycine, involved in conjugation of bile acids
-
-
?
choloyl-CoA + glycine
CoA + glycocholate
-
cholesterol degradation, glycine conjugates of bile acids occur in adult
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
conjugation of bile acids in the liver with glycine or taurine prior to being secreted into the bile duct
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine can replace glycine, involved in conjugation of bile acids
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
conjugation of the CoA adducts of bile acids with taurine
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
conjugation of bile acids with glycine or taurine favors their excretion into bile and uptake from portal blood into the liver, it promotes absorption of fat and fat-soluble vitamins in the acidic environment of the small intestine by lowering the pKa of the bile acids and hence maintaining its solubility
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine can replace glycine, involved in conjugation of bile acids
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
cholesterol degradation, bile acids are secreted as taurine conjugates in fetus and neonatus
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine-specific enzyme, gallbladder bile contains only taurine conjugates of bile acids, bile acid conjugates increases their detergent properties, prevents their precipitation in the acidic milieu of the upper small intestine, in intestines they are responsible for the solubilization and absorption of fats, vitamins and fat-soluble compounds
-
-
?
choloyl-CoA + taurine
CoA + taurocholate
-
taurine conjugates predominate in rat bile at normal hepatocellular concentrations of glycine and taurine
-
-
?
additional information
?
-
-
may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids
-
-
?
additional information
?
-
-
bile acidcoenzyme A:amino acid N-acyltransferase is the sole enzyme responsible for conjugation of primary and secondary bile acids to taurine and glycine
-
-
?
additional information
?
-
-
identification of three novel single nucleotide polymorphisms, 147C>T in exon 2 (silent), 602G>C in exon 3 (Arg201Pro), and 1134C>T in exon 4 (silent), in the gene of bile acid CoA: amino acid N-acyltransferase. The allelic frequencies are 0.005 for 147C>T, 0.095 for 602G>C, and 0.015 for 1134C>T. The two known SNPs, 59G>A (Arg20Gln, rs1572983) and UTR1513G>A (rs2229594), are detected at a frequency of 0.500 and 0.425, respectively. In the haplotype analysis for the 59G>A and 602G>C polymorphisms, the allelic frequency of 59G-602G, 59G-602C, 59A-602G and 59A-602C is 0.405, 0.095, 0.500 and 0.000, respectively. The allelic frequency of the nonsynonymous SNP 602G>C is 0.194 in a Caucasian population
-
-
?
additional information
?
-
-
may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids
-
-
?
additional information
?
-
-
bile acid-coenzyme A:amino acid N-acyltransferase is the sole enzyme responsible for conjugation of primary and secondary bile acids to taurine and glycine
-
-
?
additional information
?
-
-
suppression of rBAT occurs at the transcriptional level, and the decrease in retinoid-X receptorY-alpha by septic insult may play a critical role in rBAT suppression at the early stage of polymicrobial sepsis
-
-
?
additional information
?
-
-
the enzyme improves the survival rate of rats and increases the bile acid concentrations in in septic livers
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-hydroxynonenal
-
inactivated by 4HNE in a dose-dependent manner. The active-site His (His362) dose-dependently forms a 4-hydroxynonenal adduct, contributing to loss of activity
N-ethylmaleimide
-
10 min, at 0.2 mM: 90% loss of activity, preincubation with cholyl-CoA before NEM-treatment protects
p-mercuribenzoate
-
reversible by dithioerythritol, substrates protect, serine and alanine protect
additional information
-
not inhibited by 2-mercaptoethanol, CaCl2, EDTA, glutathione
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Pectin
-
dietary pectin relative to cellulose activates, especially the glycine-dependent activity
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Sepsis
Role of retinoid-X receptor-alpha in the suppression of rat bile acid coenzyme A-amino acid N-acyltransferase in liver during sepsis.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
higher kcat for glycine than for taurine
-
additional information
additional information
-
higher kcat for glycine than for taurine
-
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE