Information on EC 2.3.2.10 - UDP-N-acetylmuramoylpentapeptide-lysine N6-alanyltransferase

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The expected taxonomic range for this enzyme is: Weissella viridescens

EC NUMBER
COMMENTARY
2.3.2.10
-
RECOMMENDED NAME
GeneOntology No.
UDP-N-acetylmuramoylpentapeptide-lysine N6-alanyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
L-alanyl-tRNAAla + UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine = tRNAAla + UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
also acts on L-seryl-tRNA
-
-
-
L-alanyl-tRNAAla + UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine = tRNAAla + UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
catalysis via a ternary complex; transfer of L-Ala to epsilon-amino group of L-lysine of UDP-UDP-acetylmuramoylpentapeptide in an ordered sequential mechanism
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
aminoacyl group transfer
-
-
-
-
aminoacyl group transfer
-
-
PATHWAY
KEGG Link
MetaCyc Link
Peptidoglycan biosynthesis
-
peptidoglycan cross-bridge biosynthesis IV (Weissella viridescens)
-
SYSTEMATIC NAME
IUBMB Comments
L-alanyl-tRNAAla:UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine N6-alanyltransferase
Also acts on L-seryl-tRNASer.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
alanyl-transfer ribonucleate-uridine diphosphoacetylmuramoylpentapeptide transferase
-
-
-
-
alanyltransferase
-
-
alanyltransferase, uridine diphosphoacetylmuramoylpentapeptide lysine N6-
-
-
-
-
FemX
Weissella viridescens CIP 102810
-
-
-
FemXWv transferase
-
-
UDP-N-acetylmuramoylpentapeptide lysine N6-alanyltransferase
-
-
-
-
uridine diphosphoacetylmuramoylpentapeptide lysine N6-alanyltransferase
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
37257-26-4
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
strain CIP 102810 T, formerly Lactobacillus viridescens ATCC 12706
-
-
Manually annotated by BRENDA team
Weissella viridescens CIP 102810
strain CIP 102810 T, formerly Lactobacillus viridescens ATCC 12706
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
glycyl-tRNAGly + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAGly + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(glycyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
poor substrate
-
-
ir
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
-
-
?
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
-
-
-
?
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
Q9EY50
-
-
-
?
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
poor or no acceptors are acetylmuramoyl- and phosphoacetylmuramoyl-L-Ala-L-Glu-L-Lys-D-Ala-D-Ala or UDP-acetylmuramoyl-L-Ala-L-Glu-L-Lys, no strict specificity for tRNA-carrier: tRNACys can replace tRNAAla, tRNA from other species can substitute to some extent for the homologous tRNA from Lactobacillus viridescens, higher specificity for transferred amino acid: amino acids with larger substituents are no substrates, UDP-acetylmuramyl-L-Ala-D-Glu-meso-diaminopimelic acid-D-Ala-D-Ala can replace UDP-acetylmuramyl-L-Ala-D-Glu-L-Lys-D-Ala-D-Ala at 15% the transfer rate
-
ir
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
involved in peptidoglucan metabolism, responsible for interpeptide bridges
-
-
ir
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
production of precursors for branched chain peptidoglycans
-
-
?
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
Q9EY50
production of precursors for branched chain peptidoglycans, involved in the synthesis of bacterial cell walls
-
-
?
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
Weissella viridescens CIP 102810
-
-, production of precursors for branched chain peptidoglycans
-
-
?
L-alanyl-tRNASer + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNASer + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
-
-
?
L-cysteinyl-tRNACys + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNACys + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-cysteinyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
-
-
-
ir
L-seryl-tRNASer + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNASer + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-seryl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
about half as effective as L-alanyl-tRNA
-
ir
L-seryl-tRNASer + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNA + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-seryl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
-
-
?
additional information
?
-
-
also utilizes UDP-N-acetylmuramoylpentapeptide containing L-ornithine as substrate
-
-
-
additional information
?
-
-
enzyme highly specific for UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine, only traces of activity with UDP-N-acetylmuramoyl-tripeptide or UDP-N-acetylmuramoyl-tetrapeptide or derivatives of UDP-N-acetylmuramoyl-pentapeptide
-
-
-
additional information
?
-
-
catalyses the transfer of L-Ala from Ala-tRNAAla to the peptidoglycan precursor UDP-MurNAc-pentapeptide in order to introduce the first residue of an L-Ala-L-Ser-L-Ala side chain
-
-
-
additional information
?
-
-
FemXWv transferase adds the first residue of the L-Ala-L-Ser-L-Ala side chain onto the nucleotide precursor UDP-MurNAc-pentadepsipeptide
-
-
-
additional information
?
-
Weissella viridescens CIP 102810
-
enzyme highly specific for UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine, only traces of activity with UDP-N-acetylmuramoyl-tripeptide or UDP-N-acetylmuramoyl-tetrapeptide or derivatives of UDP-N-acetylmuramoyl-pentapeptide
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
involved in peptidoglucan metabolism, responsible for interpeptide bridges
-
-
ir
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
-
production of precursors for branched chain peptidoglycans
-
-
?
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
Q9EY50
production of precursors for branched chain peptidoglycans, involved in the synthesis of bacterial cell walls
-
-
?
L-alanyl-tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
tRNAAla + UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-N6-(L-alanyl)-L-lysyl-D-alanyl-D-alanine
show the reaction diagram
Weissella viridescens CIP 102810
-
production of precursors for branched chain peptidoglycans
-
-
?
additional information
?
-
-
catalyses the transfer of L-Ala from Ala-tRNAAla to the peptidoglycan precursor UDP-MurNAc-pentapeptide in order to introduce the first residue of an L-Ala-L-Ser-L-Ala side chain
-
-
-
additional information
?
-
-
FemXWv transferase adds the first residue of the L-Ala-L-Ser-L-Ala side chain onto the nucleotide precursor UDP-MurNAc-pentadepsipeptide
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
no activation by EDTA or metal ions
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
aminoacyl-tRNA analogue C
-
-
-
oxa-helixAla
-
-
-
oxa-helixGly
-
-
-
oxa-helixSer
-
-
-
Ser-tRNA
-
versus UDP-acetylmuramoylpentapeptide
-
UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
-
product inhibition
aminoacyl-tRNA analogue C'
-
-
-
additional information
-
no inhibition by EDTA or metal ions
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.015
-
Ala-tRNAAla
-
Ala-tRNAAla from E. coli, recombinant wild-type
-
0.054
-
Ala-tRNAAla
-
Ala-tRNAAla from E. coli, recombinant mutant E320Q
-
0.061
-
Ala-tRNAAla
-
Ala-tRNAAla from E. coli, recombinant mutant D109N
-
0.0017
-
L-alanyl-tRNA
-
pH 7.5, 30°C
0.0002
-
UDP-acetylmuramoylpentapeptide
-
-
0.042
-
UDP-acetylmuramoylpentapeptide
-
recombinant wild-type
0.067
-
UDP-acetylmuramoylpentapeptide
-
recombinant mutant E320Q
0.165
-
UDP-acetylmuramoylpentapeptide
-
recombinant mutant D109N
0.079
-
UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
-
pH 7.5, 30°C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
26.7
-
L-alanyl-tRNA
-
pH 7.5, 30°C
0.183
-
L-alanyl-tRNAAla
-
recombinant mutant D109N
0.917
-
L-alanyl-tRNAAla
-
recombinant mutant E320Q
11
-
L-alanyl-tRNAAla
-
recombinant wild-type
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.248
-
Ser-tRNA
-
versus UDP-acetylmuramoylpentapeptide
-
0.048
-
UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
-
product inhibition
additional information
-
additional information
-
-
-
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0024
-
aminoacyl-tRNA analogue C
-
-
-
0.0041
-
aminoacyl-tRNA analogue C'
-
-
-
0.0014
-
oxa-helixAla
-
-
-
0.067
-
oxa-helixGly
-
-
-
0.015
-
oxa-helixSer
-
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
276
-
-
purified enzyme
additional information
-
-
relative activity of FemXWv for the transfer of L-Ala from helixAla to UDP-MurNAc-pentapeptide 100%; relative activity of FemXWv for the transfer of L-Ala from helixGly to UDP-MurNAc-pentapeptide 2.9%; relative activity of FemXWv for the transfer of L-Ala from helixSer to UDP-MurNAc-pentapeptide 31%
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.8
7.2
-
L-alanyl-tRNA
7.2
7.6
-
L-seryl-tRNA
7.5
-
-
radioactive coupled FemX assay
7.5
-
-
inhibition assay
additional information
-
-
broad maximum
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.2
8.6
-
L-alanyl-tRNA, about 80% of maximal activity at pH 5.2 and pH 8.6
6.1
8.6
-
L-seryl-tRNA, about half-maximal activity at pH 6.1 and about 90% of maximal activity at pH 8.6
additional information
-
-
pK values of 5.5 and 9.3
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
25
-
-
assay at
30
-
-
assay at
30
-
-
radioactive coupled FemX assay
37
-
-
inhibition assay
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
38000
-
Q9EY50
crystal structure analysis
40000
-
-
PAGE
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
monomer
Q9EY50
1 * 38000, crystal structure analysis
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
crystallized by vapor diffusion method
Q9EY50
crystallized in the presence of UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine by vapor diffusion method
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
recombinant His-tagged wild-type and mutants from E. coli
-
recombinant proteins using His-tag
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed as intein-tagged fusion protein
Q9EY50
expression of wild-type and mutants as His-tagged proteins in Escherichia coli, in vitro transcription of tRNAs
-
wild type and mutant enzymes expressed as His-tag fusion proteins in Escherichia coli TOP10
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
D109N
-
site-directed mutagenesis, loss of 99% activity compared to the wild-type
E205Q
-
site-directed mutagenesis, unaltered activity compared to the wild-type
E215Q
-
site-directed mutagenesis, loss of 15% activity compared to the wild-type
E316Q
-
site-directed mutagenesis, loss of 60% activity compared to the wild-type
E320Q
-
site-directed mutagenesis, loss of 96% activity compared to the wild-type
F70L
-
35% loss of activity
K36M
-
activity complete abolished
K36R
-
160-fold reduction of activity, 5.4-fold increased Km for UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
R211K
-
17000-fold reduction of activity, no effect on Km for Ala-tRNA, Km for UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine higher than the highest sample concentration
Y103F
-
no effect on activity
Y215F
-
25-fold decrease of activity, increased Km for UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
Y215L
-
insoluble protein
Y256F
-
2.6-fold reduction of activity
F70L
Weissella viridescens CIP 102810
-
35% loss of activity
-
K36M
Weissella viridescens CIP 102810
-
activity complete abolished
-
R211K
Weissella viridescens CIP 102810
-
17000-fold reduction of activity, no effect on Km for Ala-tRNA, Km for UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine higher than the highest sample concentration
-
Y103F
Weissella viridescens CIP 102810
-
no effect on activity
-
Y215F
Weissella viridescens CIP 102810
-
25-fold decrease of activity, increased Km for UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
-
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
medicine
Q9EY50
potential target for antimicrobial drugs
medicine
-
Fem transferases are considered attractive targets for the development of novel antibiotics active against multiply resistant bacteria
medicine
-
Fem transferases are considered as attractive targets for the development of novel antibiotics active against multi-resistant bacteria