Heparan sulfate structure

Rabenstein DL. Heparin and heparan sulfate structure and function. Nat Pro Rep 2002 19 312-331. 

Heparin and hyaluronic acid will not act as acceptors for the enzyme (El, J17), whereas chondroitin 4-sulfate is at best a very poor acceptor (El, J17). The Enzyme Nomenclature Handbook (E4) quotes two sul-fatotransferases concerned with heparan sulfate structures desulfato-heparin sulfatotranferase (EC 2.8.2.S) and heparan sulfate sulfatotransferase (EC 2.8.2.12), but the contents of the relevant references quoted in the Handbook (El and S55, respectively) do not permit any distinction between the two supposed enzymes, nor do the reports discussed... 

Rabenstein, D. L. (2002). Heparin and heparan sulfate Structure and function. Natural Product Reports, 19(3), 312-331. 

Some of the polysaccharides constituting intermediate stages in the biosynthesis of heparin have been physically isolated.23 Their structure is strikingly similar to those of heparan sulfates,24 thus re-opening the often-raised question as to whether heparan sulfate indeed represents products of incomplete biosynthesis of heparin. A detailed account of the structure and biological properties of heparan sulfate is beyond the scope of this article. However, in view of similarities of structural fea-... 

Murthy, K. H., et al. (2001). Crystal structure of a complement control protein that regulates both pathways of complement activation and binds heparan sulfate proteoglycans. Cell 104,301-311. 

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.

I Capila, MJ Hernaiz, YD Mo, TR Mealy, B Campos, RJ Linhardt, BA Seaton. Annexin V-heparin oligosaccharide complex suggests heparan sulfate-mediated assembly on cell surface. Structure 9 57-64, 2001. 

Stnictures 1. Characteristic structural motifs in heparan sulfate and heparin... 

Structures 5. Structures of heparan sulfate model oligosaccharides. DS=degree of sulfation, cf. Structures 4... 

The sulfonated calix[8]arene 27 (Structures 8), which can be viewed as a simplified y-CD with the carbohydrate backbone replaced by an aryl moiety, mimicked heparin in the stimulation of heparan sulfate synthesis from cultured endothelial cells [62]. 

Coombe, D. R. and Kett, W. C. (2005). Heparan sulfate-protein interactions Therapeutic potential through structure-function insights. Cell. Mol. Life Sci. 62, 410-424. 

Fig. 4.1.3 Structure of heparan sulfate. Cleavage sites for lysosomal enzymes are also indicated...

Heparinoid polysaccharides such as heparan sulfate and heparin are able to interact with numerous proteins and influence vital biological processes. Heparinoid mimetics were prepared to reduce the structural complexity of heparinoids and to obtain selectivities. This article summarizes the development of heparinoid mimetics of different classes including representative syntheses and biological activities. Largely simplified compounds with regard to structure and synthetic access are described which maintain or exceed the activity of heparinoid polysaccharides. One of the recipes to increase binding or modify pharmacokinetic parameters was the introduction of hydrophobic groups. 

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