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Information on EC 4.1.3.3 - N-acetylneuraminate lyase
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4.1.3.3 N-acetylneuraminate lyaseIUBMB Comments
This enzyme is involved in the degradation of N-acetylneuraminate. It is specific for the open form of the sugar. It also acts on N-glycoloylneuraminate and on O-acetylated sialic acids, other than 4-O-acetylated derivatives.
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Word Map
- 4.1.3.3
- mannac
-
2-epimerase
- n-acetylmannosamine
- aldolases
-
n-glycolylneuraminic
-
cmp-sialic
- dihydrodipicolinate
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3.2.1.18
- biotechnology
- neu5gc
- dhdps
- synthesis
- n-acylneuraminate
- analysis
- industry
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
n-acetylneuraminate lyase, sialic acid aldolase, n-acetylneuraminic acid aldolase, n-acetylneuraminic acid lyase, neu5ac aldolase, n-acetyl-d-neuraminic acid aldolase, neuac lyase, n-acetylneuraminate pyruvate lyase, n-acetylneuraminate pyruvate-lyase, neuraminic acid aldolase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Acetylneuraminate pyruvate-lyase
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class I NAL
Lyase, acetylneuraminate
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N-acetyl-d-neuraminic acid aldolase
N-acetyl-D-neuraminic acid lyase
N-Acetylneuraminate aldolase
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N-Acetylneuraminate lyase
N-acetylneuraminate pyruvate lyase
N-Acetylneuraminate pyruvate-lyase
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N-Acetylneuraminic acid aldolase
N-Acetylneuraminic acid lyase
N-Acetylneuraminic aldolase
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N-Acetylneuraminic lyase
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NAL
NALase
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NanA
NANA lyase
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Neu5Ac aldolase
Neu5Ac lyase
NeuAc aldolase
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Neuraminate aldolase
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Neuraminic acid aldolase
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Neuraminic aldolase
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NPL
Sialate lyase
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Sialic acid aldolase
Sialic aldolase
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N-Acetylneuraminate lyase
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N-acetylneuraminate pyruvate lyase
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N-Acetylneuraminic acid aldolase
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N-Acetylneuraminic acid lyase
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NPL
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Sialic acid aldolase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
aceneuramate = N-acetyl-D-mannosamine + pyruvate
mechanism
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aceneuramate = N-acetyl-D-mannosamine + pyruvate
the enzyme catalyzes a Bi-Uni ordered condensation reaction in which pyruvate binds first to the enzyme to form a catalytically important Schiff base. Tyr137 acts as the proton donor to the aldehyde oxygen of ManNAc during the reaction, the activation barrier is dominated by carbon-carbon bond formation, and proton transfer from Tyr137 is required to obtain a stable Neu5Ac-Lys165 Schiff base complex. A triad of residues, Tyr137, Ser47, and Tyr110 from a neighboring subunit, are required to correctly position Tyr137 for its function
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aceneuramate = N-acetyl-D-mannosamine + pyruvate
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C-C-bond cleavage
condensation
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elimination
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of an oxo-acid, C-C bond cleavage
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
aceneuramate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
This enzyme is involved in the degradation of N-acetylneuraminate. It is specific for the open form of the sugar. It also acts on N-glycoloylneuraminate and on O-acetylated sialic acids, other than 4-O-acetylated derivatives.
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CAS REGISTRY NUMBER
COMMENTARY
9027-60-5
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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
(2R,3R,4R)-6-[(aminooxy)carbonyl]-3,4,6-trihydroxy-N-propyltetrahydro-2H-pyran-2-carboxamide
?
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?
(2S,4S,5R,6R)-5-(acetylamino)-6-[(dipropylamino)carbonyl]-2,4-dihydroxytetrahydro-pyran-2-carboxylic acid
?
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-
-
-
?
(5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid
pyruvate + (2R,3S)-2,3-dihydroxy-4-oxo-N,N-dipropylbutanamide
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-
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r
2-deoxy-2-[[(alpha-D-galactopyranosyloxy)acetyl]amino]-D-mannopyranose + pyruvate
3,5-dideoxy-5-[[(alpha-D-galactopyranosyloxy)acetyl]amino]-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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36% yield
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?
2-deoxy-2-[[(beta-D-galactopyranosyloxy)acetyl]amino]-D-mannopyranose + pyruvate
3,5-dideoxy-5-[[(beta-D-galactopyranosyloxy)acetyl]amino]-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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34% yield
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?
3-bromo-3-deoxy-D-mannose + pyruvate
?
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wild-type enzyme: 5% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 5% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 10% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 10% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 10% of the activity with N-acetyl-D-mannosamine
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-
?
4-O-alpha-D-galactopyranosyl-D-mannopyranose + pyruvate
3-deoxy-7-O-alpha-D-galactopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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5% yield
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?
4-O-beta-D-galactopyranosyl-D-mannopyranose + pyruvate
3-deoxy-7-O-beta-D-galactopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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38% yield
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?
4-O-beta-D-glucopyranosyl-D-mannopyranose + pyruvate
3-deoxy-7-O-beta-D-glucopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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35% yield
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?
5-N-acetyl-4-O-acetylneuraminic acid
?
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22% the activity with N-acetylneuraminic acid
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?
5-O-alpha-D-galactopyranosyl-alpha-D-mannofuranose + pyruvate
3-deoxy-8-O-alpha-D-galactopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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62% yield
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?
5-O-beta-D-galactopyranosyl-alpha-D-mannofuranose + pyruvate
3-deoxy-8-O-beta-D-galactopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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85% yield
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?
5-O-methyl-N-acetyl-D-mannosamine + pyruvate
8-O-methyl-N-acetylneuraminate
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-
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?
6-O-alpha-D-galactopyranosyl-D-mannopyranose + pyruvate
3-deoxy-9-O-alpha-D-galactopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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81% yield
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?
6-O-alpha-D-glucopyranosyl-D-mannopyranose + pyruvate
3-deoxy-9-O-alpha-D-glucopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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65% yield
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?
6-O-alpha-D-mannopyranosyl-D-mannopyranose + pyruvate
3-deoxy-9-O-alpha-D-mannopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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78% yield
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?
6-O-beta-D-glucopyranosyl-D-mannopyranose + pyruvate
3-deoxy-9-O-beta-D-glucopyranosyl-D-glycero-beta-D-galacto-non-2-ulopyranosonic acid
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83% yield
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?
D-arabinose + pyruvate
D-3-deoxy-manno-2-octulosonic acid
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wild-type enzyme: 20% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 40% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 65% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 40% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 85% of the activity with N-acetyl-D-mannosamine
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r
D-glucose + pyruvate
?
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wild-type enzyme: 40% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 40% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 20% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 25% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 20% of the activity with N-acetyl-D-mannosamine
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?
D-gulose + pyruvate
?
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wild-type enzyme: 10% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 110% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 90% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 70% of the activity with N-acetyl-D-mannosamine
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?
D-mannosamine + pyruvate
?
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wild-type enzyme: 80% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 90% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 165% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 190% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 170% of the activity with N-acetyl-D-mannosamine
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?
D-mannose + pyruvic acid
2-keto-3-deoxy-D-glycero-D-galacto-nonopyranulosonic acid
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?
D-talose + pyruvate
?
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wild-type enzyme: 60% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 50% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 105% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 80% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 70% of the activity with N-acetyl-D-mannosamine
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?
L-arabinose + pyruvate
L-3-deoxy-manno-2-octulosonic acid
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wild-type enzyme: 10% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 35% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 70% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 40% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 80% of the activity with N-acetyl-D-mannosamine
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r
L-mannose + pyruvate
?
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wild-type enzyme: 80% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 110% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 95% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 95% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 95% of the activity with N-acetyl-D-mannosamine
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?
N-acetyl-D-mannosamine + pyruvate
N-acetyl-D-neuraminic acid
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r
N-acetyl-L-mannosamine + pyruvate
N-acetyl-L-neuraminic acid
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wild-type enzyme: 0.2% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 0.5% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 1% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 2% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 2% of the activity with N-acetyl-D-mannosamine
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r
N-acetylneuraminic acid
pyruvate + N-acetyl-D-mannosamine
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r
pyruvate + alpha-D-Galp-(1,6)-D-Manp
alpha-D-Galp-(1,9)-D-deoxyneuraminic acid
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?
2-deoxy-D-glucose + pyruvate
?
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33% activity compared to N-acetylneuraminate
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r
2-deoxy-D-glucose + pyruvate
?
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33% activity compared to N-acetylneuraminate
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r
2-deoxy-D-glucose + pyruvate
?
1.2% activity compared to N-acetylneuraminate
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r
2-deoxy-D-glucose + pyruvate
?
Limosilactobacillus antri DSMZ 16041
1.2% activity compared to N-acetylneuraminate
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r
5-N-acetyl-9-O-acetylneuraminic acid
?
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54% the activity with N-acetylneuraminic acid
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?
5-N-acetyl-9-O-acetylneuraminic acid
?
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32.45% the activity with N-acetylneuraminic acid
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?
5-N-acetyl-9-O-acetylneuraminic acid
?
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45% the activity with N-acetylneuraminic acid
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?
D-arabinose + pyruvate
3-deoxy-D-manno-2-octulosonic acid
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1.0% activity compared to N-acetylneuraminate
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r
D-arabinose + pyruvate
3-deoxy-D-manno-2-octulosonic acid
1.5% activity compared to N-acetylneuraminate
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r
D-mannose + pyruvate
?
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wild-type enzyme: 30% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 15% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 70% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 80% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 75% of the activity with N-acetyl-D-mannosamine
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?
D-mannose + pyruvate
?
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95% activity compared to N-acetylneuraminate
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r
D-mannose + pyruvate
?
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95% activity compared to N-acetylneuraminate
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r
D-mannose + pyruvate
?
10% activity compared to N-acetylneuraminate
-
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r
D-mannose + pyruvate
?
Limosilactobacillus antri DSMZ 16041
10% activity compared to N-acetylneuraminate
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r
D-xylose + pyruvate
?
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wild-type enzyme: 45% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 40% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 55% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 25% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 25% of the activity with N-acetyl-D-mannosamine
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?
D-xylose + pyruvate
?
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2.4% activity compared to N-acetylneuraminate
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r
D-xylose + pyruvate
?
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2.4% activity compared to N-acetylneuraminate
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r
D-xylose + pyruvate
?
0.6% activity compared to N-acetylneuraminate
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r
D-xylose + pyruvate
?
Limosilactobacillus antri DSMZ 16041
0.6% activity compared to N-acetylneuraminate
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r
L-gulose + pyruvate
?
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wild-type enzyme: 70% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I: 35% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/V251I/V265I: 15% of the activity with N-acetyl-D-mannosamine, mutant enzyme Y98H/F115L/N153Y/V251I/V265I/Y281C: 15% of the activity with N-acetyl-D-mannosamine, mutant enzyme E60A/Y98H/F115L/N153Y/D150G/V251I/V265I/Y281C/N153Y: 15% of the activity with N-acetyl-D-mannosamine
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?
L-gulose + pyruvate
?
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3.6% activity compared to N-acetylneuraminate
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r
L-gulose + pyruvate
?
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3.6% activity compared to N-acetylneuraminate
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r
L-gulose + pyruvate
?
0.7% activity compared to N-acetylneuraminate
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r
L-gulose + pyruvate
?
Limosilactobacillus antri DSMZ 16041
0.7% activity compared to N-acetylneuraminate
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r
N-acetyl-D-mannosamine + pyruvate
N-acetylneuraminate
-
-
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r
N-acetyl-D-mannosamine + pyruvate
N-acetylneuraminate
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-
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r
N-acetyl-D-mannosamine + pyruvate
N-acetylneuraminate
the enzyme catalyzes the retro-aldol cleavage of N-acetylneuraminic acid to form N-acetyl-D-mannosamine and pyruvate
-
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r
N-acetyl-D-mannosamine + pyruvate
N-acetylneuraminate
the enzyme catalyzes the retro-aldol cleavage of N-acetylneuraminic acid to form N-acetyl-D-mannosamine and pyruvate
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r
N-acetyl-D-mannosamine + pyruvate
N-acetylneuraminate
reversible aldol condensation of pyruvate and N-acetyl-D-mannosamine
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r
N-acetyl-D-mannosamine + pyruvate
N-acetylneuraminate
reversible aldol condensation of pyruvate and N-acetyl-D-mannosamine
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r
N-Acetyl-D-mannosamine + pyruvate
N-Acetylneuraminic acid
-
-
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r
N-Acetyl-D-mannosamine + pyruvate
N-Acetylneuraminic acid
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-
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r
N-acetyl-D-neuraminic acid
N-acetyl-D-mannosamine + pyruvate
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in presence of excess pyruvate the equilibrium may be driven in the direction of aldol product formation
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r
N-acetyl-D-neuraminic acid
N-acetyl-D-mannosamine + pyruvate
-
-
-
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r
N-acetyl-D-neuraminic acid
pyruvate + N-acetyl-D-mannosamine
-
-
-
-
r
N-acetyl-D-neuraminic acid
pyruvate + N-acetyl-D-mannosamine
-
-
-
-
r
N-acetyl-neuraminic acid
N-acetyl-D-mannosamine + pyruvate
-
-
-
-
r
N-Acetylmannosamine + pyruvate
?
-
N-acetylneuraminic acid is intermediate for colomic acid biosynthesis
-
-
?
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
-
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
the enzyme catalyzes the reversible condensation of pyruvate with N-acetyl-D-mannosamine to yield the sialic acid N-acetylneuraminic acid
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
100% activity
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
100% activity
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
100% activity
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
Limosilactobacillus antri DSMZ 16041
100% activity
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
reversible aldol cleavage of N-acetylneuraminic acid
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
-
-
?
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
-
-
r
N-acetylneuraminate
N-acetyl-D-mannosamine + pyruvate
-
-
-
r
N-Acetylneuraminic acid
?
Corynebacterium belfanti
-
metabolized by pathogens parasitizing on mucous membranes
-
-
?
N-Acetylneuraminic acid
?
-
metabolized by pathogens parasitizing on mucous membranes
-
-
?
N-Acetylneuraminic acid
?
-
metabolized by pathogens parasitizing on mucous membranes
-
-
?
N-Acetylneuraminic acid
?
-
metabolized by pathogens parasitizing on mucous membranes
-
-
?
N-Acetylneuraminic acid
?
-
N-acetylneuraminate lyase plays important role in regulation of N-acetylneuraminic acid metabolism
-
-
?
N-Acetylneuraminic acid
?
-
metabolized by pathogens parasitizing on mucous membranes
-
-
?
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
-
-
?
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
-
-
r
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
-
r
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
-
r
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
-
r
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
-
-
?
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
-
-
?
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
?
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
r
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
syn: Neu5Ac
-
r
N-Acetylneuraminic acid
N-Acetyl-D-mannosamine + pyruvate
-
-
-
-
?
N-Acetylneuraminic acid
N-A