Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A.
Summary of "Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A."
Chondroitin sulfate-E (chondroitin-4, 6-disulfate) was prepared from chondroitin sulfate-A (chondroitin-4 - sulfate) by regioselective sulfonation, performed using trimethylamine sulfur trioxide in formamide under argon. The structure of semi-synthetic chondroitin sulfate-E was analyzed by PAGE, (1)H NMR, (13)C NMR, 2D NMR and disaccharide analysis and compared with natural chondroitin sulfate-E. Both semi-synthetic and natural chondroitin sulfate-E were each biotinylated and immobilized on BIAcore SA biochips and their interactions with fibroblast growth factors displayed very similar binding kinetics and binding affinities. The current semi-synthesis offers an economical approach for the preparation of the rare chondroitin sulfate-E from the readily available chondroitin sulfate-A.
This article was published in the following journal.
Name: Carbohydrate polymers
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22140285
- DOI: http://dx.doi.org/10.1016/j.carbpol.2011.08.075
Chondroitin sulfates (CSs) have characteristic bioactivities that depend on sulfation patterns. Chemically synthesized CS oligosaccharides are valuable tools for elucidating the relationship between s...
Osteoarthritis is a common, progressive joint disease, and treatments generally aim for symptomatic improvement. However, SYmptomatic Slow-Acting Drugs in Osteoarthritis (SYSADOAs) not only reduce joi...
Glycosaminoglycans (GAGs) are important sulfated carbohydrates prevalently found in the extracellular matrix that serve many biological functions. The synthesis of structurally diverse but defined GAG...
Glycosaminoglycan (GAG) side chains of proteoglycans are involved in a wide variety of developmental and pathophysiological functions. Similar to a gene knockout, the ability to inhibit GAG biosynthes...
Heparanase-1 activation, albuminuria, and a decrease in glomerular heparan sulfate (HS) have been described in diabetic nephropathy (DN). Glycosaminoglycan (GAG)-based drugs have been shown to have re...
This study was conducted to evaluate the efficacy and safety of prednisolone and chloroquine add on therapies to combined glucosamine, chondroitin sulfate in osteoarthritis of the knee whi...
The purpose of this study is to assess the efficacy and safety of glucosamine and chondroitin sulfate association in the treatment of patients with osteoarthrosis of the knee.
The purpose of this study is to examine the way the dietary supplements glucosamine and chondroitin are absorbed and distributed throughout the body.
The purpose of this study is to determine the effect of a chondroitin sulphate conventional treatment on the degree of severity of synovitis, as measured by magnetic resonance in patients ...
The purpouse of this study is to determine the efficacy and safety of chondroitin sulphate conventional treatment in patients with both knee osteoarthritis and plaque psoriasis.
Medical and Biotech [MESH] Definitions
Derivatives of chondroitin which have a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate.
Enzymes which catalyze the elimination of glucuronate residues from chondroitin A,B, and C or which catalyze the hydrolysis of sulfate groups of the 2-acetamido-2-deoxy-D-galactose 6-sulfate units of chondroitin sulfate. EC 4.2.2.-.
Enzymes which catalyze the elimination of delta-4,5-D-glucuronate residues from polysaccharides containing 1,4-beta-hexosaminyl and 1,3-beta-D-glucuronosyl or 1,3-alpha-L-iduronosyl linkages thereby bringing about depolymerization. EC 22.214.171.124 acts on chondroitin sulfate A and C as well as on dermatan sulfate and slowly on hyaluronate. EC 126.96.36.199 acts on chondroitin sulfate A and C.
Proteoglycans consisting of proteins linked to one or more CHONDROITIN SULFATE-containing oligosaccharide chains.
A naturally occurring glycosaminoglycan found mostly in the skin and in connective tissue. It differs from CHONDROITIN SULFATE A (see CHONDROITIN SULFATES) by containing IDURONIC ACID in place of glucuronic acid, its epimer, at carbon atom 5. (from Merck, 12th ed)