Synthesis of Glycosaminoglycans

Medel Manuel L. Zulueta, Shu-Yi Lin, Yu-Peng Hu, AND SHANG-CHENG HUNG 

Genomics Research Center, Academia Sinica, Taipei, Taiwan 

Glycochemical Synthesis Strategies and Applications, First Edition. 

FIGURE 10.1 Some monosaccharide building blocks used in the assembly of (a) HA, (b) CS, and (c) heparin/HS showing the array of protecting groups. All, allyl Bn, benzyl Bz, benzoyl Fmoc, 9-fluorenylmethoxycarbonyl Lev, levulinyl NAP, 2-naphthylmethyl PBB, p-bromobenzyl Phth, phthaloyl PMB, / -methoxybenzyl PMP, p-methoxyphenyl TBDPS, ferf-butyldiphenylsilyl TBS, ferf-butyldimethylsilyl TCA, trichloroacetyl TDS, dimethylthexylsilyl Tol, 4-tolyl. 

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The dolichol-linked D-mannosyl, D-glucosyl, and 2-acetamido-2-deoxy-D-glucosyl residues are used in the glycosylation of proteins and in the biosynthesis of D-m an nan.2,35 GlcNAc-PP-Dol may also play a role in the synthesis of glycosaminoglycans. Reaction 4 is the first step in the formation of lipid-linked precursors for cellulose.46... 

Schachtschabel, D.O. and Wever, J., Age-related decline in the synthesis of glycosaminoglycans by cultured human fibroblasts, Mech. Aging Dev., 8, 257, 1978. 

During these years, our work laid the foundation for future studies on the effect of elastoviscous solutions of hyaluronan on the migration, proliferation and function of white blood cells, and how such solutions affect some functions of the immune system. We discovered that hyaluronan regulates the synthesis of glycosaminoglycans in in vitro systems, and regulates inflammation and tissue regeneration in adult animal models and tissues. All these studies laid the theoretical foundation for the therapeutic applications of hyaluronan. 

Horwitz AL, Crystal RC. Content and synthesis of glycosaminoglycans in the developing lung. J Clin Invest 1975 56 1312-1318. 

Hyaluronan represented 91 % of the total glycosaminoglycans synthesized by normal vitreous. Vitreous fibrosis was induced by intravitreal injection of monocytes and lymphocytes (55). In the fibrotic vitreous, the synthesis of hyaluronan was decreased to 30%, whereas the synthesis of chondroitin sulfate was increased to 47% of the total newly synthesized glycosaminoglycans. Similarly, vitreous fibrosis was induced by intravitreal injection of erythrocytes (56). In the fibrotic vitreous, the synthesis of hyaluronan was decreased to 26%, whereas the synthesis of chondroitin sulfate increased to 59% of the total newly synthesized glycosaminoglycans. These results suggest that blood cells may alter the synthesis of glycosaminoglycans in induced fibrotic vitreous. 

Katakami C, Raymond LA, Lipman MJ, Appel A, Kao WW. Change in the synthesis of glycosaminoglycans by fibrotic vitreons indnced by erythrocytes. Biochim Biophys Acta 1986 880 40-45. 

Kahaly G, Stover C, Beyer J, Otto E. In vitro synthesis of glycosaminoglycans in endocrine ophthalmopathy. Acta Endocrinol (Copenh) 1992 127 397-402. 

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