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Literature summary for 2.4.1.133 extracted from

  • Thorsheim, K.; Willen, D.; Tykesson, E.; Stahle, J.; Praly, J.P.; Vidal, S.; Johnson, M.T.; Widmalm, G.; Manner, S.; Ellervik, U.
    Naphthyl thio- and carba-xylopyranosides for exploration of the active site of beta-1,4-galactosyltransferase 7 (beta4GalT7) (2017), Chemistry, 23, 18057-18065 .
    View publication on PubMed
Search for more literature for 2.4.1.133

Cloned(Commentary)

Cloned (Comment) Organism
gene B4GALT7, recombinant expression of His6-GST-tagged enzyme Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information Michaelis-Menten kinetics Homo sapiens
0.025
-
 2-naphthyl 1,5-dithio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
0.034
-
 2-naphthyl 5-thio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
0.36
-
 naphthalen-2-yl 1-thio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
0.39
-
 (1R,2S,3R,4R)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol pH 6.2, 37°C, recombinant enzyme Homo sapiens
0.78
-
 naphthalen-2-yl beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein] Homo sapiens
-
 UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein]
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens Q9UBV7
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His6-GST-tagged enzyme by nickel affinity chromatography Homo sapiens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information synthesis of xyloside analogues with substitution of the endocyclic oxygen atom by sulfur or carbon and investigation of them as substrates for beta-1,4-galactosyltransferase 7 (beta4GalT7), overview. The analogues with an endocyclic sulfur atom prove to be excellent substrates for b4GalT7, and are galactosylated approx. fifteen times more efficiently than the corresponding xyloside. The 5a-carba-beta-xylopyranoside in the D-configuration proves to be a good substrate for beta4GalT7, whereas the enantiomer in the L-configuration shows no activity. X-ray crystallography, NMR spectroscopy, and molecular modeling provide a rationale for the pronounced activity of the sulfur analogues. Favorable Pi-Pi interactions between the 2-naphthyl moiety and a tyrosine side chain of the enzyme are observed for the thio analogues (1S,2R,3S,4S)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol, 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one, and 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one. The carbaxyloside of iliparcil are synthesized as well as its L-xylo-enantiomers 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one and 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one. The L-xylo-derivative 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one shows a much higher antithrombotic activity compared to the D-xylo-enantiomer 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one and only the compound with L-xylo conformation functions as substrate for beta4GalT7 when assayed with enzyme extracts from chicken embryo. This is in stark contrast to other investigations where L-enantiomers of xylosides rarely act as substrates for beta4GalT7. Quantum mechanical calculations and docking simulations, overview Homo sapiens ?
-
-
UDP-alpha-D-galactose + (1R,2S,3R,4R)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol
-
 Homo sapiens UDP + ?
-
 ?
UDP-alpha-D-galactose + (1S,2R,3S,4S)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol
-
 Homo sapiens UDP + ?
-
 ?
UDP-alpha-D-galactose + 2-naphthyl 1,5-dithio-beta-D-xylopyranoside
-
 Homo sapiens UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-1,5-dithio-beta-D-xylopyranoside
-
 ?
UDP-alpha-D-galactose + 2-naphthyl 5-thio-beta-D-xylopyranoside
-
 Homo sapiens UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside
-
 ?
UDP-alpha-D-galactose + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl beta-D-carbaxylopyranoside a 5a-carba-beta-xylopyranoside Homo sapiens UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-beta-D-carbaxylopyranoside
-
 ?
UDP-alpha-D-galactose + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl beta-L-carbaxylopyranoside a 5a-carba-beta-xylopyranoside Homo sapiens UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-beta-L-carbaxylopyranoside
-
 ?
UDP-alpha-D-galactose + beciparcil a 5-thio-beta-D-xylopyranoside Homo sapiens UDP + 4-[(4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranosyl)thio]benzonitrile
-
 ?
UDP-alpha-D-galactose + iliparcil a 5-thio-beta-D-xylopyranoside Homo sapiens UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside
-
 ?
UDP-alpha-D-galactose + naphthalen-2-yl 1-thio-beta-D-xylopyranoside
-
 Homo sapiens UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-1-thio-beta-D-xylopyranoside
-
 ?
UDP-alpha-D-galactose + naphthalen-2-yl beta-D-xylopyranoside
-
 Homo sapiens UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
-
 ?
UDP-alpha-D-galactose + naroparcil a 5-thio-beta-D-xylopyranoside Homo sapiens UDP + 4-[4-[(4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranosyl)thio]benzoyl]benzonitrile
-
 ?
UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein]
-
 Homo sapiens UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein]
-
 ?
UDP-alpha-D-galactose + odiparcil a 5-thio-beta-D-xylopyranoside Homo sapiens UDP + 4-methyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside
-
 ?

Synonyms

Synonyms Comment Organism
beta-1,4-galactosyltransferase 7
-
 Homo sapiens
beta4GalT7
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Homo sapiens

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.6
-
 2-naphthyl 1,5-dithio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
2
-
 2-naphthyl 5-thio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
2.7
-
 (1R,2S,3R,4R)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol pH 6.2, 37°C, recombinant enzyme Homo sapiens
2.7
-
 naphthalen-2-yl 1-thio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
3.1
-
 naphthalen-2-yl beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.2
-
 assay at Homo sapiens

General Information

General Information Comment Organism
metabolism beta-1,4-galactosyltransferase 7 (beta4GalT7) is a key enzyme in the biosynthesis of glycosaminoglycan chains Homo sapiens
additional information molecular docking complex of the beta4GalT7 mutant D211N from Drosophila melanogaster with substrates naphthalen-2-yl beta-D-xylopyranoside, naphthalen-2-yl 1-thio-beta-D-xylopyranoside, 2-naphthyl 5-thio-beta-D-xylopyranoside, and 2-naphthyl 1,5-dithio-beta-D-xylopyranoside Homo sapiens

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.97
-
 naphthalen-2-yl beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
6.92
-
 (1R,2S,3R,4R)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol pH 6.2, 37°C, recombinant enzyme Homo sapiens
7.5
-
 naphthalen-2-yl 1-thio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
58.8
-
 2-naphthyl 5-thio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens
64
-
 2-naphthyl 1,5-dithio-beta-D-xylopyranoside pH 6.2, 37°C, recombinant enzyme Homo sapiens