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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
random attack
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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
stepwise attack
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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate
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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate
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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate
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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate
[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate, lytic mechanism with Tyr242 acting as a general base that abstracts the proton from the C5 position of glucuronic acid while Asn183 and His233 neutralize the charge on the glucuronate acidic group, substrate binding site
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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate, mechanism, active site structure, His225, Tyr234, Arg288, and Glu371 form a catalytic tetrad
[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate, random endolytic elimination mechanism
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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate, reaction mechanism
-
[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate, stepwise reaction mechanism
-
[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
acts on chondroitin 4-sulfate and chondroitin 6-sulfate, but less well on hyaluronate
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[1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]n = n-1 4-deoxy-beta-D-gluc-4-enuronosyl-1,4-beta-D-hexosylamine + [1,3-beta-D-glucuronic acid-1,4-beta-D-hexosylamine]
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4-O-(2',4'-dinitrophenyl)-beta-D-glucopyranosiruronic acid
?
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?
benzyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid
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benzyl 4-O-(2',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid
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benzyl 4-O-(2'-nitrophenyl)-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
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?
benzyl 4-O-(3',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
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?
benzyl 4-O-(4'-chloro-2'-nitrophenyl)-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
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benzyl S-(2-acetamido-2-deoxy-beta-D-galactopyranosyl)-(1-4)-4-deoxy-4-thio-beta-D-glucopyranosiduronic acid
?
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very slow cleavage, 9% product after 24 h
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?
chondroitin 4-sulfate
2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose
chondroitin sulfate A
unsaturated chondroitin A sulfate disaccharide
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i.e. chondroitin 4-sulfate
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?
chondroitin sulfate C
unsaturated chondroitin sulfate C disaccharide
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i.e. chondroitin 6-sulfate
product analysis
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chondroitin sulfate/dermatan sulfate chain
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chondroitin AC I lyase cleaves the linkage between GalNAc and D-GlcA, with the formation of a 4,5 double bond at HexA and a water molecule elimination
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chondroitin/dermatan sulfate chain
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chon-AC-lyase cleaves the linkage between GalNAc and D-GlcA
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GlcNAc-D-glucuronic acid-GlcNAc-D-glucuronic acid
DELTA-4,5-uronic acid-GlcNAc + N-acetyl-D-glucosamine + DELTA-4,5-glucuronic acid
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heparan sulfate
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wild-type enzyme and mutants R292A, R288A, and Y234F
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hyaluronan methyl ester
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hyaluronate
hyaluronate oligosaccharides
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methyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
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phenyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid
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phenyl 4-methylumbelliferyl-beta-D-glucopyranosiduronic acid
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phenyl 4-O-(2',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid
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?
proteoglycan
protein-keratan sulfate
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the protein-keratan sulfate core isolated after limit digestion of proteoglycan contains about 44% protein, 38% keratan sulfate, and 18% of the enzymatically modified oligosaccharide attachment region between the chondroitin sulfate chains and protein core: gluco-4-enepyranosyluronic acid-(galactosyl)2-xylose
?
additional information
?
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benzyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
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?
benzyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
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?
benzyl 4-O-(2',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
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?
benzyl 4-O-(2',4'-dinitrophenyl)-beta-D-glucopyranosiduronic acid
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synthetic chromogenic substrate
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chondroitin
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chondroitin
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degradation is faster than with chondroitin 4-sulfate or chondroitin 6-sulfate
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chondroitin
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best substrate
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chondroitin
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degradation is faster than with chondroitin 4-sulfate or chondroitin 6-sulfate
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chondroitin 4-sulfate
2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose
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?
chondroitin 4-sulfate
2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose
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?
chondroitin 4-sulfate
2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose
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?
chondroitin 4-sulfate
2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose
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?
chondroitin 4-sulfate
2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose
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i.e. chondroitin sulfate A
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?
chondroitin 4-sulfate
2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose
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?
chondroitin 4-sulfate
2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulfo-D-galactose
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?
chondroitin 4-sulfate
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61% of the activity with hyaluronic acid
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chondroitin 4-sulfate
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ACII lyase is an exolytic enzyme able to cut the polysaccharide chains starting from the nonreducing end
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chondroitin 4-sulfate
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exolytic action pattern
the products afforded by chondroitinase ACII contain primarily unsaturated disaccharide
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chondroitin 4-sulfate
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chondroitin AC lyase is specific for chondroitin 4-sulfate and has endolytic activity
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chondroitin 4-sulfate
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random endolytic action pattern
the products of chondroitinase AC contain unsaturated oligosaccharides of sizes ranging from disaccharide to decasaccharide
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chondroitin 4-sulfate
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chondroitin 4-sulfate
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chondroitin 6-sulfate
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86% of the activity with hyaluronic acid
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chondroitin 6-sulfate
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chondroitin 6-sulfate
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chondroitin 6-sulfate
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exolytic action pattern
the products afforded by chondroitinase ACII contain primarily unsaturated disaccharide
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chondroitin 6-sulfate
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chondroitin 6-sulfate
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i.e. chondroitin sulfate C
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chondroitin 6-sulfate
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the degradation of chondroitin by an anionic E1cb elimination mechanism involves proton abstraction from C5 of glucuronic acid, Tyr234 is the key base catalysts
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chondroitin 6-sulfate
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random endolytic action pattern
the products of chondroitinase AC contain unsaturated oligosaccharides of sizes ranging from disaccharide to decasaccharide
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chondroitin 6-sulfate
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chondroitin 6-sulfate
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chondroitin sulfate A
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i.e. chondroitin 4-sulfate, best substrate
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chondroitin sulfate A
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relative activity: 100% (recombinant protein), 100% (native protein)
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chondroitin sulfate A
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i.e. chondroitin 4-sulfate, best substrate
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chondroitin sulfate A
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chondroitin sulfate A
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i.e. chondroitin 4-sulfate
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chondroitin sulfate A
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chondroitin sulfate A
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i.e. chondroitin 4-sulfate
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chondroitin sulfate A
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i.e. chondroitin 4-sulfate
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chondroitin sulfate A
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i.e. chondroitin 4-sulfate
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chondroitin sulfate A
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i.e. chondroitin 4-sulfate
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chondroitin sulfate A
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i.e. chondroitin 4-sulfate, best substrate, wild-type enzyme and mutants R292A, R288A, H225A and Y234F
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chondroitin sulfate A
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chondroitin sulfate B
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chondroitin sulfate B
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate, low activity
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chondroitin sulfate C
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relative activity: 42% (recombinant protein), 46% (native protein)
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate, low activity
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chondroitin sulfate C
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate
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chondroitin sulfate C
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate
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?
chondroitin sulfate C
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i.e. chondroitin 6-sulfate
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chondroitin sulfate C
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i.e. chondroitin 6-sulfate, wild-type enzyme and mutants R292A, R288A, and Y234F
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chondroitin sulfate C
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chondroitin sulfate D
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chondroitin sulfate D
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chondroitin sulfate E
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chondroitin sulfate E
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dermatan sulfate
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dermatan sulfate
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dermatan sulfate
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wild-type enzyme and mutants R292A, and Y234F
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hyaluronan
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hyaluronate
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hyaluronate
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degradation is faster than with chondroitin 4-sulfate or chondroitin 6-sulfate
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hyaluronate
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degradation is faster than with chondroitin 4-sulfate or chondroitin 6-sulfate
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hyaluronic acid
?
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hyaluronic acid
?
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low activity
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hyaluronic acid
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relative activity: 54% (recombinant protein), 67% (native protein)
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hyaluronic acid
?
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low activity
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hyaluronic acid
?
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hyaluronic acid
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wild-type enzyme and mutants R292A, R288A, and Y234F
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hyaluronic acid
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hyaluronic acid
?
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hyaluronic acid
?
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phenyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
-
?
phenyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
-
?
phenyl 4-methylumbelliferyl-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
-
?
phenyl 4-methylumbelliferyl-beta-D-glucopyranosiduronic acid
?
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synthetic chromogenic substrate
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?
additional information
?
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no activity with dermatan sufate, heparin and heparan sulfate, the latter of porcine or bovine source
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?
additional information
?
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no activity with dermatan sulfate or heparin as substrate
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additional information
?
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no activity with dermatan sufate, heparin and heparan sulfate, the latter of porcine or bovine source
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additional information
?
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constitutive enzyme
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additional information
?
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chondroitin AC lyase activity is significantly related to the virulence of the strains at 25°C. ChonAC activity is significantly higher in the high virulence group than in the low virulence group at 25°C
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additional information
?
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chondroitin/dermatan sulfate chain of decorin, with a high complexity due to the large variety of glycoforms, from human skin fibroblasts is released by reductive beta-elimination reaction and digested with chondroitin AC I lyase. Mass spectrometric substrate and product analysis, e.g. tetrasulfated octasaccharide, decasaccharides, a trisulfated, a hexasulfated [4,5-D-GlcAGalNAc(IdoAGalNAc)4], and [4,5-D-GlcAGalNAc(IdoAGalNAc)3], and disaccharides, overview
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additional information
?
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the enzyme als acts as an exoglycosidase towards hyaluronate
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additional information
?
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no activity with dermatan sulfate
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additional information
?
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substrate specificity, no activity with dermatan sulfate
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additional information
?
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Arg292 is involved in recognition of the N-acetyl and sulfate moieties of galactosamine, but does not participate directly in catalysis
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additional information
?
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developement of an assay using synthetic substrates, which can be monitored by 3 different techniques, UV-Vis spectroscopy, fluorescence spectroccopy, and fluoride ion-selective electrode usage, overview, products of chondroitin sulfate cleavages are disaccharides or oligosaccharides with DELTA4,5-unsaturated uronic acid resdiues at the nonreducing end, methyl 4-deoxy-4-fluoro-beta-D-glucopyranosiduronic acid is a poor substrate
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?
additional information
?
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elimination mechanism, but no syn-elimination, resulting in disaccharides or oligosaccharides with DELTA4,5-unsaturated uronic acid residues at the nonreducing end
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?
additional information
?
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the active site forms a tunnel, structurally involved residue Arg292 is responsible for substrate recognition of N-acetyl or O-sulfo moieties in galactosamine residues, it does not participate in catalysis
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additional information
?
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constitutive enzyme
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additional information
?
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digestion of amyloid fibrils with chondroitinase AC hydrolyzes keratan sulfate and heparan sulfate
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additional information
?
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does not split endogalactosaminidic bonds neighbouring to reduced disaccharide units
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additional information
?
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no activity with chondroitin sulfate B, heparin or heparan sulfate
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?
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4.2.2.5 chondroitin AC lyase
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