Synthetic probes of glycosaminoglycan function

Current Opinion in Chemical Biology

Volumn 17, Issue 6, 2013, Pages 1014-1022

  Griffin, Matthew E ^a   Hsieh Wilson, Linda C ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOKINE; FONDAPARINUX; GLYCAN; GLYCOSAMINOGLYCAN; GROWTH FACTOR; LOW MOLECULAR WEIGHT HEPARIN; OLIGOSACCHARIDE; POLYMER; VIRUS RECEPTOR;

BIOLOGICAL FUNCTIONS; DRUG SUBSTITUTION; HUMAN; IN VIVO STUDY; MODULATION; MOLECULAR PROBE; PROTEIN FUNCTION; PROTEIN INTERACTION; PROTEIN STRUCTURE; PROTHROMBIN TIME; REVIEW; SULFATION; SYNTHESIS;

ANIMALS; BIOMIMETIC MATERIALS; BIOMIMETICS; GLYCOSAMINOGLYCANS; HUMANS; OLIGOSACCHARIDES;

EID: 84890150079     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2013.09.015     Document Type: Review

References (48)

1. Capila I., Linhardt R.J. Heparin-protein interactions. Angew Chem Int Ed 2002, 41:390-412.
2. Sugahara K., Mikami T. Chondroitin/dermatan sulfate in the central nervous system. Curr Opin Struct Biol 2007, 17:536-545.
3. Shen Y., Tenney A.P., Busch S.A., Horn K.P., Cuascut F.X., Liu K., He Z., Silver J., Flanagan J.G. PTPσ is a receptor for chondroitin sulfate proteoglycan, an inhibitor of neural regeneration. Science 2009, 326:592-596.
4. Coles C.H., Shen Y., Tenney A.P., Siebold C., Sutton G.C., Lu W., Gallagher J.T., Jones E.Y., Flanagan J.G., Aricescu A.R. Proteoglycan-specific molecular switch for RPTPσ clustering and neuronal extension. Science 2011, 332:484-488.
5. Brown J.M., Xia J., Zhuang B.Q., Cho K-S., Rogers C.J., Gama C.I., Rawat M., Tully S.E., Uetani N., Mason D.E., et al. A sulfated carbohydrate epitope inhibits axon regeneration after injury. Proc Natl Acad Sci U S A 2012, 109:4768-4773.
6. Sasisekharan R., Shriver Z., Venkataraman G., Narayanasami U. Roles of heparan-sulphate glycosaminoglycans in cancer. Nat Rev Cancer 2002, 2:521-528.
7. Taylor K.R., Gallo R.L. Glycosaminoglycans and their proteoglycans: host-associated molecular patterns for initiation and modulation of inflammation. FASEB J 2006, 20:9-22.
8. Bishop J.R., Schuksz M., Esko J.D. Heparan sulphate proteoglycans fine-tune mammalian physiology. Nature 2007, 446:1030-1037.
9. Orgueira H.A., Bartolozzi A., Schell P., Litjens R.E.J.N., Palmacci E.R., Seeberger P.H. Modular synthesis of heparin oligosaccharides. Chem Eur J 2003, 9:140-169.
10. de Paz J.L., Martin-Lomas M. Synthesis and biological evaluation of a heparin-like hexasaccharide with the structural motifs for binding to FGF and FGFR. Eur J Org Chem 2005, 1849-1858.
11. Polat T., Wong C-H. Anomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides. J Am Chem Soc 2007, 129:12795-12800.
12. Arungundram S., Al-Mafraji K., Asong J., Leach F.E., Amster I.J., Venot A., Turnbull J.E., Boons G-J. Modular synthesis of heparan sulfate oligosaccharides for structure-activity relationship studies. J Am Chem Soc 2009, 131:17394-17405.
13. Baleux F., Loureiro-Morais L., Hersant Y., Clayette P., Arenzana-Seisdedos F., Bonnaffé D., Lortat-Jacob H. A synthetic CD4-heparan sulfate glycoconjugate inhibits CCR5 and CXCR4 HIV-1 attachment and entry. Nat Chem Biol 2009, 5:743-748.
14. Hu Y-P., Zhong Y-Q., Chen Z-G., Chen C-Y., Shi Z., Zulueta M.M.L., Ku C-C., Lee P-Y., Wang C-C., Hung S-C. Divergent synthesis of 48 heparan sulfate-based disaccharides and probing the specific sugar-fibroblast growth factor-1 interaction. J Am Chem Soc 2012, 134:20722-20727.
15. Hansen S.U., Miller G.J., Cole C., Rushton G., Avizienyte E., Jayson G.C., Gardiner J.M. Tetrasaccharide iteration synthesis of a heparin-like dodecasaccharide and radiolabelling for in vivo tissue distribution studies. Nat Commun 2013, 4:2016.
16. Gama C.I., Tully S.E., Sotogaku N., Clark P.M., Rawat M., Vaidehi N., Goddard W.A., Nishi A., Hsieh-Wilson L.C. Sulfation patterns of glycosaminoglycans encode molecular recognition and activity. Nat Chem Biol 2006, 2:467-473.
17. Lopin C., Jacquinet J-C. From polymer to size-defined oligomers: an expeditious route for the preparation of chondroitin oligosaccharides. Angew Chem Int Ed 2006, 45:2574-2578.
18. Vibert A., Lopin-Bon C., Jacquinet J-C. From polymer to size-defined oligomers: a step economy process for the efficient and stereocontrolled construction of chondroitin oligosaccharides and biotinylated conjugates thereof: Part 1. Chem Eur J 2009, 15:9561-9578.
19. Jacquinet J-C., Lopin-Bon C., Vibert A. From polymer to size-defined oligomers: a highly divergent and stereocontrolled construction of chondroitin sulfate A, C, D, E, K, L, and M oligomers from a single precursor: Part 2. Chem Eur J 2009, 15:9579-9595.
20. Eller S., Collot M., Yin J., Hahm H.S., Seeberger P.H. Automated solid-phase synthesis of chondroitin sulfate glycosaminoglycans. Angew Chem Int Ed 2013, 52:5858-5861.
21. Choay J., Petitou M., Lormeau J.C., Sinaÿ P., Casu B., Gatti G. Structure-activity relationship in heparin: a synthetic pentasaccharide with high affinity for antithrombin III and eliciting high anti-factor Xa activity. Biochem Biophys Res Commun 1983, 116:492-499.
22. Petitou M., van Boeckel C.A.A. A synthetic antithrombin III binding pentasaccharide is now a drug! What comes next?. Angew Chem Int Ed 2004, 43:3118-3133.
23. Petitou M., Casu B., Lindahl U. 1976-1983, a critical period in the history of heparin: the discovery of the antithrombin binding site. Biochimie 2003, 85:83-89.
24. de Paz J.L., Moseman E.A., Noti C., Polito L., von Andrian U.H., Seeberger P.H. Profiling heparin-chemokine interactions using synthetic tools. ACS Chem Biol 2007, 2:735-744.
25. Cole C.L., Hansen S.U., Baráth M., Rushton G., Gardiner J.M., Avizienyte E., Jayson G.C. Synthetic heparan sulfate oligosaccharides inhibit endothelial cell functions essential for angiogenesis. PLoS ONE 2010, 5:e11644.
26. Hu Y-P., Lin S-Y., Huang C-Y., Zulueta M.M.L., Liu J-Y., Chang W., Hung S-C. Synthesis of 3-O-sulfonated heparan sulfate octasaccharides that inhibit the herpes simplex virus type 1 host-cell interaction. Nat Chem 2011, 3:557-563.
27. Shukla D., Liu J., Blaiklock P., Shworak N.W., Bai X., Esko J.D., Cohen G.H., Eisenberg R.J., Rosenberg R.D., Spear P.G. A novel role for 3-O-sulfated heparan sulfate in herpes simplex virus 1 entry. Cell 1999, 99:13-22.
28. Rogers C.J., Clark P.M., Tully S.E., Abrol R., Garcia K.C., Goddard W.A., Hsieh-Wilson L.C. Elucidating glycosaminoglycan-protein-protein interactions using carbohydrate microarray and computational approaches. Proc Natl Acad Sci U S A 2011, 108:9747-9752.
29. Liu J., Shworak N.W., Sinaÿ P., Schwartz J.J., Zhang L., Fritze L.M.S., Rosenberg R.D. Expression of heparan sulfate d-glucosaminyl 3-O-sulfotransferase isoforms reveals novel substrate specificities. J Biol Chem 1999, 274:5185-5192.
30. Zhang L., Beeler D.L., Lawrence R., Lech M., Liu J., Davis J.C., Shriver Z., Sasisekharan R., Rosenberg R.D. 6-O-Sulfotransferase-1 represents a critical enzyme in the anticoagulant heparan sulfate biosynthetic pathway. J Biol Chem 2001, 276:42311-42321.
31. Xu D., Moon A.F., Song D., Pedersen L.C., Liu J. Engineering sulfotransferases to modify heparan sulfate. Nat Chem Biol 2008, 4:200-202.
32. Chappell E.P., Liu J. Use of biosynthetic enzymes in heparin and heparan sulfate synthesis. Bioorg Med Chem 2013, 21:4786-4792.
33. Kuberan B., Lech M.Z., Beeler D.L., Wu Z.L., Rosenberg R.D. Enzymatic synthesis of antithrombin III-binding heparan sulfate pentasaccharide. Nat Biotechnol 2003, 21:1343-1346.
34. Xu Y., Masuko S., Takieddin M., Xu H., Liu R., Jing J., Mousa S.A., Linhardt R.J., Liu J. Chemoenzymatic synthesis of homogeneous ultralow molecular weight heparins. Science 2011, 334:498-501.
35. Petitou M, Jacquinet J-C, Sinaÿ P, Choay J, Lormeau J-C, Nassr M: Process for the organic synthesis of oligosaccharides and derivatives thereof. US Patent 1989, 4818816.
36. Sugiura N., Shimokata S., Minamisawa T., Hirabayashi J., Kimata K., Watanabe H. Sequential synthesis of chondroitin oligosaccharides by immobilized chondroitin polymerase mutants. Glycoconj J 2008, 25:521-530.
37. Sugiura N., Shioiri T., Chiba M., Sato T., Narimatsu H., Kimata K., Watanabe H. Construction of a chondroitin sulfate library with defined structures and analysis of molecular interactions. J Biol Chem 2012, 287:43390-43400.
38. de Paz J.L., Noti C., Böhm F., Werner S., Seeberger P.H. Potentiation of fibroblast growth factor activity by synthetic heparin oligosaccharide glycodendrimers. Chem Biol 2007, 14:879-887.
39. Rawat M., Gama C.I., Matson J.B., Hsieh-Wilson L.C. Neuroactive chondroitin sulfate glycomimetics. J Am Chem Soc 2008, 130:2959-2961.
40. Lee S-G., Brown J.M., Rogers C.J., Matson J.B., Krishnamurthy C., Rawat M., Hsieh-Wilson L.C. End-functionalized glycopolymers as mimetics of chondroitin sulfate proteoglycans. Chem Sci 2010, 1:322-325.
41. Sheng G.J., Oh Y.I., Chang S-K., Hsieh-Wilson L.C. Tunable heparan sulfate mimetics for modulating chemokine activity. J Am Chem Soc 2013, 135:10898-10901.
42. Young E. The anti-inflammatory effects of heparin and related compounds. Thromb Res 2008, 122:743-752.
43. Plante O.J., Palmacci E.R., Seeberger P.H. Automated solid-phase synthesis of oligosaccharides. Science 2001, 291:1523-1527.
44. Hsu C-H., Hung S-C., Wu C-Y., Wong C-H. Toward automated oligosaccharide synthesis. Angew Chem Int Ed 2011, 50:11872-11923.
45. Bhaskar U., Sterner E., Hickey A.M., Onishi A., Zhang F., Dordick J.S., Linhardt R.J. Engineering of routes to heparin and related polysaccharides. Appl Microbiol Biotechnol 2012, 93:1-16.
46. Dougherty M.J., Arnold F.H. Directed evolution: new parts and optimized function. Curr Opin Biotechnol 2009, 20:486-491.
47. DeAngelis P.L. Glycosaminoglycan polysaccharide biosynthesis and production: today and tomorrow. Appl Microbiol Biotechnol 2012, 94:295-305.
48. Oh Y.I., Sheng G.J., Chang S.-K., Hsieh-Wilson L.C. Tailored glycopolymers as anticoagulant heparin mimetics. Angew Chem Int Ed 2013, 52:11796-11799. Angew Chem 2013, 125:12012-12015.