Biosynthesis of chondroitin sulfate. Microsomal acceptors of sulfate, glucuronic acid, and N-acetylgalactosamine

Biochemistry ◽  
1973 ◽  
Vol 12 (20) ◽  
pp. 3898-3903 ◽  
Author(s):  
Martha E. Richmond ◽  
Silvana DeLuca ◽  
Jeremiah E. Silbert
Keyword(s):  
Chondroitin Sulfate ◽  
Glucuronic Acid

scholarly journals Unexpected loss of stereoselectivity in glycosylation reactions during the synthesis of chondroitin sulfate oligosaccharides

2019 ◽  
Vol 15 ◽  
pp. 137-144 ◽  
Author(s):  
Teresa Mena-Barragán ◽  
José L de Paz ◽  
Pedro M Nieto
Keyword(s):  
Chondroitin Sulfate ◽  
Exploratory Study ◽  
Glucuronic Acid ◽  
Building Blocks ◽  
Significant Loss ◽  
Efficient Synthesis ◽  
Substitution Pattern ◽  
The Impact

Here, we present an exploratory study on the fluorous-assisted synthesis of chondroitin sulfate (CS) oligosaccharides. Following this approach, a CS tetrasaccharide was prepared. However, in contrast to our previous results, a significant loss of β-selectivity was observed in [2 + 2] glycosylations involving N-trifluoroacetyl-protected D-galactosamine donors and D-glucuronic acid (GlcA) acceptors. These results, together with those obtained from experiments employing model monosaccharide building blocks, highlight the impact of the glycosyl acceptor structure on the stereoselectivity of glycosylation reactions. Our study provides useful data about the substitution pattern of GlcA units for the efficient synthesis of CS oligomers.

scholarly journals 2,3-Di-O-sulfo glucuronic acid: An unmodified and unusual residue in a highly sulfated chondroitin sulfate from Litopenaeus vannamei

2018 ◽  
Vol 183 ◽  
pp. 192-200 ◽  
Author(s):  
Rômulo S. Cavalcante ◽  
Adriana S. Brito ◽  
Lais C.G.F. Palhares ◽  
Marcelo A. Lima ◽  
Renan P. Cavalheiro ◽  
...  
Keyword(s):  
Chondroitin Sulfate ◽  
Litopenaeus Vannamei ◽  
Glucuronic Acid

scholarly journals Structure and Anti-Inflammatory Activity of a New Unusual Fucosylated Chondroitin Sulfate from Cucumaria djakonovi

Marine Drugs ◽  
2018 ◽  
Vol 16 (10) ◽  
pp. 389 ◽  
Author(s):  
Nadezhda Ustyuzhanina ◽  
Maria Bilan ◽  
Elena Panina ◽  
Nadezhda Sanamyan ◽  
Andrey Dmitrenok ◽  
...  
Keyword(s):  
Chondroitin Sulfate ◽  
Salmo Salar ◽  
Glucuronic Acid ◽  
Inflammatory Activity ◽  
Eastern Coast ◽  
Chondroitin Sulfates ◽  
Anti Inflammatory ◽  
Non Destructive ◽  
Inflammatory Effect

Fucosylated chondroitin sulfate CD was isolated from the sea cucumber Cucumaria djakonovi collected from the Avachinsky Gulf of the eastern coast of Kamchatka. Structural characterization of CD was performed using a series of non-destructive NMR spectroscopic procedures. The polysaccharide was shown to contain a chondroitin core [→3)-β-d-GalNAc-(1→4)-β-d-GlcA-(1→]n where about 60% of GlcA residues were 3-O-fucosylated, while another part of GlcA units did not contain any substituents. The presence of unsubstituted both at O-2 and O-3 glucuronic acid residues in a structure of holothurian chondroitin sulfate is unusual and has not been reported previously. Three different fucosyl branches Fucp2S4S, Fucp3S4S and Fucp4S were found in the ratio of 2:1:1. The GalNAc units were mono- or disulfated at positions 4 and 6. Anti-inflammatory activity of CD was assessed on a model of acute peritoneal inflammation in rats. About 45% inhibition was found for CD, while a structurally related linear chondroitin sulfate SS from cartilage of the fish Salmo salar demonstrated only 31% inhibition, indicating that the presence of sulfated fucosyl branches is essential for anti-inflammatory effect of chondroitin sulfates of marine origin.

scholarly journals Chondroitinase-mediated Degradation of Rare 3-O-Sulfated Glucuronic Acid in Functional Oversulfated Chondroitin Sulfate K and E

2007 ◽  
Vol 282 (51) ◽  
pp. 36895-36904 ◽  
Author(s):  
Duriya Fongmoon ◽  
Ajaya Kumar Shetty ◽  
Basappa ◽  
Shuhei Yamada ◽  
Makiko Sugiura ◽  
...  
Keyword(s):  
Chondroitin Sulfate ◽  
Glucuronic Acid ◽  
Oversulfated Chondroitin Sulfate ◽  
Sulfated Glucuronic Acid

scholarly journals Molecular Cloning and Characterization of a Novel Chondroitin Sulfate Glucuronyltransferase That Transfers Glucuronic Acid toN-Acetylgalactosamine

2002 ◽  
Vol 277 (41) ◽  
pp. 38179-38188 ◽  
Author(s):  
Masanori Gotoh ◽  
Toshikazu Yada ◽  
Takashi Sato ◽  
Tomohiro Akashima ◽  
Hiroko Iwasaki ◽  
...  
Keyword(s):  
Chondroitin Sulfate ◽  
Molecular Cloning ◽  
Glucuronic Acid

scholarly journals PAPAIN-INDUCED CHANGES IN RABBIT CARTILAGE

1958 ◽  
Vol 108 (4) ◽  
pp. 507-513 ◽  
Author(s):  
Theodore T. Tsaltas
Keyword(s):  
Chondroitin Sulfate ◽  
Intravenous Injection ◽  
Glucuronic Acid ◽  
Cartilage Matrix ◽  
Rabbit Cartilage ◽  
Induced Changes ◽  
Histologic Changes ◽  
Rabbit Ears

Some biochemical aspects of the collapse of the rabbit ears produced by the intravenous injection of papain have been studied. A marked depletion of chondromucoprotein (M.C.S.) and a reduction of the S35 content of cartilage matrix were found to coincide with the gross and histologic changes in the cartilage. At the same time there was a marked increase in the amount of S35 in the serum and an increase of S35 and glucuronic acid excreted in the urine. Alteration in the composition of the M.C.S. remaining in the cartilage of the papain-injected animals was detected. The findings indicate that the collapse of the rabbit ears is due to loss of chondromucoprotein from cartilage and reduction of chondroitin sulfate in the chondromucoprotein that remains. All these changes were reversed in recovery.

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