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Literature summary extracted from

  • Campeotto, I.; Bolt, A.H.; Harman, T.A.; Dennis, C.; Trinh, C.H.; Phillips, S.E.; Nelson, A.; Pearson, A.R.; Berry, A.
    Structural insights into substrate specificity in variants of N-acetylneuraminic acid lyase produced by directed evolution (2010), J. Mol. Biol., 404, 56-69.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.1.3.3 His-tagged version expressed in Escherichia coli BL21 Escherichia coli

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
4.1.3.3 sitting drop diffusion method, PEG 3350 Escherichia coli

Protein Variants

EC Number Protein Variants Comment Organism
4.1.3.3 E192A strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192C strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192D strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192F strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192G strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192H strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192I strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192K strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192L strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192M strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192N strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192P strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192Q strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192R strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192S strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192T strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192V strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192W strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli
4.1.3.3 E192Y strong interaction of Glu192 (wild type) with hydroxyl groups at C8 and C9 of N-acetylneuraminic acid Escherichia coli

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.1.3.3 (2R,3R)-2,3,4-trihydroxy-N,N-dipropylbutanamide competitive inhibitor Escherichia coli

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.1.3.3 0.2
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192M mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.2
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192P mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.3
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192F mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.4
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192N mutant protein, pH 7.7.5, 25°C Escherichia coli
4.1.3.3 0.4
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192V mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.5
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192H mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.6
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192S mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.7
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192Q mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 1.1
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192D mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 3.5
-
 N-acetylneuraminic acid E192Q mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 4.4
-
 N-acetylneuraminic acid wild type (E192), pH 7.5, 25°C Escherichia coli
4.1.3.3 4.6
-
 N-acetylneuraminic acid E192D mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 5
-
 N-acetylneuraminic acid E192M mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 5.9
-
 N-acetylneuraminic acid E192F mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 6
-
 N-acetylneuraminic acid E192P mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 6
-
 N-acetylneuraminic acid E192S mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 6.2
-
 N-acetylneuraminic acid E192H mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 11
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid wild type (E192), pH 7.5, 25°C Escherichia coli
4.1.3.3 34
-
 N-acetylneuraminic acid E192V mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 38
-
 N-acetylneuraminic acid E192N mutant protein, pH 7.7.5, 25°C Escherichia coli

Organism

EC Number Organism UniProt Comment Textmining
4.1.3.3 Escherichia coli
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.1.3.3 immobilized metal ion affinity chromatography (Ni2+), gel filtration Escherichia coli

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.1.3.3 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid
-
 Escherichia coli pyruvate + (2R,3S)-2,3-dihydroxy-4-oxo-N,N-dipropylbutanamide
-
 r
4.1.3.3 N-acetylmannosamine + pyruvate
-
 Escherichia coli N-acetylneuraminic acid
-
 r
4.1.3.3 N-acetylneuraminic acid
-
 Escherichia coli N-acetylmannosamine + pyruvate
-
 r

Synonyms

EC Number Synonyms Comment Organism
4.1.3.3 N-Acetylneuraminic acid aldolase
-
 Escherichia coli
4.1.3.3 N-Acetylneuraminic acid lyase
-
 Escherichia coli
4.1.3.3 Sialic acid aldolase
-
 Escherichia coli

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
4.1.3.3 0.1
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192D mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.42
-
 N-acetylneuraminic acid E192P mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.43
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192S mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.63
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192H mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.82
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192P mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.83
-
 N-acetylneuraminic acid E192S mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 1.17
-
 N-acetylneuraminic acid E192M mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 1.17
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192M mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 1.22
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid wild type (E192), pH 7.5, 25°C Escherichia coli
4.1.3.3 1.47
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192F mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 1.58
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192V mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 2
-
 N-acetylneuraminic acid E192D mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 2
-
 N-acetylneuraminic acid E192H mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 2
-
 N-acetylneuraminic acid E192V mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 2.17
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192N mutant protein, pH 7.7.5, 25°C Escherichia coli
4.1.3.3 2.67
-
 N-acetylneuraminic acid E192F mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 2.83
-
 N-acetylneuraminic acid E192N mutant protein, pH 7.7.5, 25°C Escherichia coli
4.1.3.3 2.83
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192Q mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 4.33
-
 N-acetylneuraminic acid wild type (E192), pH 7.5, 25°C Escherichia coli
4.1.3.3 5
-
 N-acetylneuraminic acid E192Q mutant protein, pH 7.5, 25°C Escherichia coli

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
4.1.3.3 1.3
-
 (2R,3R)-2,3,4-trihydroxy-N,N-dipropylbutanamide E192N mutant protein , pH 7.5, 25°C Escherichia coli

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
4.1.3.3 0.06
-
 N-acetylneuraminic acid E192V mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.07
-
 N-acetylneuraminic acid E192N mutant protein, pH 7.7.5, 25°C Escherichia coli
4.1.3.3 0.07
-
 N-acetylneuraminic acid E192P mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.08
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192D mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.12
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid wild type (E192), pH 7.5, 25°C Escherichia coli
4.1.3.3 0.13
-
 N-acetylneuraminic acid E192S mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.23
-
 N-acetylneuraminic acid E192M mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.32
-
 N-acetylneuraminic acid E192H mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.43
-
 N-acetylneuraminic acid E192D mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.45
-
 N-acetylneuraminic acid E192F mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.7
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192S mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 0.98
-
 N-acetylneuraminic acid wild type (E192), pH 7.5, 25°C Escherichia coli
4.1.3.3 1.33
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192H mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 1.42
-
 N-acetylneuraminic acid E192Q mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 4.17
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192Q mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 4.33
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192P mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 4.5
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192V mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 5.17
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192F mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 5.33
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192M mutant protein, pH 7.5, 25°C Escherichia coli
4.1.3.3 5.67
-
 (5R,6R)-7-(dipropylamino)-4,5,6-trihydroxy-2,7-dioxoheptanoic acid E192N mutant protein, pH 7.7.5, 25°C Escherichia coli