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Literature summary extracted from

  • Spickenreither, M.; Braun, S.; Bernhardt, G.; Dove, S.; Buschauer, A.
    Novel 6-O-acylated vitamin C derivatives as hyaluronidase inhibitors with selectivity for bacterial lyases (2006), Bioorg. Med. Chem. Lett., 16, 5313-5316.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.2.1.35 (2S)-2-(3,4-dimethoxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl hexadecaneperoxoate inactive at concentrations less than 0.2 mM, at pH 5.0 Bos taurus
3.2.1.35 (2S)-2-[3,4-bis(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexadecaneperoxoate inactive at concentrations less than 0.2 mM, at pH 5.0 Bos taurus
3.2.1.35 (5R)-3,4-bis(benzyloxy)-5-(1,2-dihydroxyethyl)furan-2(5H)-one inactive at concentrations less than 13 mM, at pH 5.0 Bos taurus
3.2.1.35 (5R)-5-(1,2-dihydroxyethyl)-3,4-dimethoxyfuran-2(5H)-one inactive at concentrations less than 13 mM, at pH 5.0 Bos taurus
3.2.1.35 (7S)-7-(1,2-dihydroxyethyl)-2,3-dihydrofuro[3,4-b][1,4]dioxin-5(7H)-one inactive at concentrations less than 13 mM, at pH 5.0 Bos taurus
3.2.1.35 2-hydroxy-2-[(5R)-7-oxo-2,3,5,7-tetrahydrofuro[3,4-b][1,4]dioxin-5-yl]ethyl hexadecaneperoxoate inactive at concentrations less than 0.2 mM, at pH 5.0 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl ([1-[2-(benzyloxy)ethenylidene]but-2-yn-1-yl]oxy)ethaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 11-phenoxyundecaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 11-[[1-(2-phenylethenylidene)but-2-yn-1-yl]oxy]undecaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 2,2-dimethylpropaneperoxoate inactive at concentrations less than 1.1 mM, at pH 5.0 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 3-(2-phenylethenylidene)hex-4-yneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 6-(benzyloxy)hexaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 6-phenoxyhexaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl benzenecarboperoxoate 33% inhibition at 1.43 mM Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl decaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl dodecaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexadecaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl octadecaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl octaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl tetradecaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl tridecaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl undecaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl [(1-prop-1-yn-1-ylpenta-1,2-dien-1-yl)oxy]ethaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl [[1-(2-phenylethenylidene)but-2-yn-1-yl]oxy]ethaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl [[2-(2-phenylethenylidene)pent-3-yn-1-yl]oxy]ethaneperoxoate
-
 Bos taurus
3.2.1.35 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl {[1-(2-phenylethenylidene)but-2-yn-1-yl]oxy}ethaneperoxoate
-
 Bos taurus
3.2.1.35 L-ascorbic acid inactive at concentrations less than 100 mM, at pH 5.0 Bos taurus

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.35 Bos taurus
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.2.1.35 testicle
-
 Bos taurus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.35 hyaluronan + 2 H2O
-
 Bos taurus N-acetyl-beta-D-glucosamine + D-glucuronate + ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.2.1.35 BTH
-
 Bos taurus
3.2.1.35 hyaluronidase
-
 Bos taurus
3.2.1.35 Neopermease commercial preparation Bos taurus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.2.1.35 0.037
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 11-[[1-(2-phenylethenylidene)but-2-yn-1-yl]oxy]undecaneperoxoate
3.2.1.35 0.039
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl octadecaneperoxoate
3.2.1.35 0.057
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl hexadecaneperoxoate
3.2.1.35 0.071
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl tetradecaneperoxoate
3.2.1.35 0.096
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl tridecaneperoxoate
3.2.1.35 0.105
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 11-phenoxyundecaneperoxoate
3.2.1.35 0.188
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl [[1-(2-phenylethenylidene)but-2-yn-1-yl]oxy]ethaneperoxoate
3.2.1.35 0.208
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl dodecaneperoxoate
3.2.1.35 0.21
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl ([1-[2-(benzyloxy)ethenylidene]but-2-yn-1-yl]oxy)ethaneperoxoate
3.2.1.35 0.543
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl [[2-(2-phenylethenylidene)pent-3-yn-1-yl]oxy]ethaneperoxoate
3.2.1.35 0.58
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl undecaneperoxoate
3.2.1.35 1.38
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl decaneperoxoate
3.2.1.35 2.006
-
 at pH 5.0 Bos taurus 2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl 3-(2-phenylethenylidene)hex-4-yneperoxoate