Chondroitin sulfate, structure

N. Volpi, Chondroitin Sulfate Structure, Role and Pharmacological Activity, Amsterdam, Boston, Heidelberg, London, New York, Oxford, Paris, San Diego, San Francisco, Singapore, Sydney, Tokyo, Academic Press, 2006. 

Caterson, B., Mahmoodian, E, Sorrell, J.M., Hardingham, T.E., Bayliss, M.T., Carney, S.L., Ratcliffe, A. and Muii H. (1990) Modulation of native chondroitin sulfate structure in tissue development and in disease . Journal of Cell Science, 97, 411-17. 

This substance is widely distributed in animal tissues. Its structure is similar to that of chondroitin sulfate, ex-... 

Chondroitin sulfates are located at sites of calcification in endochondral bone and are also found in cartilage. They are also located inside certain neurons and may provide an endoskeletal structure, helping to maintain their shape. 

The methylated derivatives served as the basis of elegant studies in which Jeanloz and his colleagues unequivocally established the structure of hyaluronan, dermatan sulfate, and the chondroitin sulfates. They also clarified many confusing issues, including the position of the sulfate groups in these polymers. In the course of this work, they proved that dermatan sulfate contained L-iduronic acid, a sugar not known before to occur in nature. 

Due to its similar structure to chondroitin sulfate and its ability to absorb 200-300 times its weight in water, many investigators have hypothesized that this brown... 

Figure 3. Conformation of the K chondroitin 4-sulfate structure viewed normal to and along the helix axis. The 03 05 hydrogen bonds are shown by broken lines. (Reproduced with permission from ref. 18. Copyright 1983 Academic Press Inc.)...

Fig. 2 Structures of the major and minor disaccharide sequences of heparin and heparan sulfate as well as the major disaccharide units of chondroitin sulfate, dermatan sulfate, keratan sulfate, and hyaluronic acid, where Ac is acetyl.

FIGURE 2.1 Structures of disaccharides forming chondroitin sulfate. Adapted from Volpi (2007). With permission from Wiley Publisher. 

Gargiulo, V., Lanzetta, R., Parrilli, M., and De Castrol, C. (2009). Structural analysis of chondroitin sulfate from Scyliorhinus canicula A useful source of this polysaccharide. Glycobiology 19,1485-1491. 

Sugahara, K., Mikami, T., Uyama, T., Mizuguchi, S., Nomura, K., and Kitagawa, H. (2003). Recent advances in the structural biology of chondroitin sulfate and dermatan sulfate. Curr. Opin. Struct. Biol. 13, 612-620. 

Fig. 4.1.1 Structure of chondroitin sulfate. Cleavage sites for lysosomal enzymes are also indicated (arrows). MPS Mucopolysaccharidosis...

Model building in the computer is used to analyze the conformational effects of steric interactions between atoms of the polymer skeleton for x-carrageenan, t-carrageenan, A-carrageenan, agar, chondroltin, chondroitin sulfates, dermatan sulfate, keratan sulfate, hyaluronic acid, and related polysaccharides. Over 99% of the conformations are thus excluded and virtually all of the remainder for each polysaccharide lie close together. Predictions are also made from disaccharide crystal structures and checked against experimental results. 

FIGURE 7-26 Proteoglycan structure, showing the trisaccharide bridge. A typical trisaccharide linker (blue) connects a glycosaminoglycan—in this case chondroitin sulfate (orange)—to a Ser residue (red) in the core protein. The xylose residue at the reducing end of the linker is joined by its anomeric carbon to the hydroxyl of the Ser residue. 

Evidence for the structure of the main repeating-chain of chondroitin sulfate, as well as the sequence at the linkage region to protein, has come... 

---