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Divergent synthesis of 48 heparan sulfate-based disaccharides and probing the specific sugar-fibroblast growth factor-1 interaction.

Hu YP, Zhong YQ, Chen ZG, Chen CY, Shi Z, Zulueta MM, Ku CC, Lee PY, Wang CC, Hung SC
J Am Chem Soc 134 20722-7 (2012)
Related entries: 3ud8, 3ud9, 3uda

Cited: 40 times
EuropePMC logo PMID: 23240683

Abstract

Several biological processes involve glycans, yet understanding their ligand specificities is impeded by their inherent diversity and difficult acquisition. Generating broad synthetic sugar libraries for bioevaluations is a powerful tool in unraveling glycan structural information. In the case of the widely distributed heparan sulfate (HS), however, the 48 theoretical possibilities for its repeating disaccharide call for synthetic approaches that should minimize the effort in an undoubtedly huge undertaking. Here we employed a divergent strategy to afford all 48 HS-based disaccharides from just two orthogonally protected disaccharide precursors. Different combinations and sequence of transformation steps were applied with many downstream intermediates leading up to multiple target products. With the full disaccharide library in hand, affinity screening with fibroblast growth factor-1 (FGF-1) revealed that four of the synthetic sugars bind to FGF-1. The molecular details of the interaction were further clarified through X-ray analysis of the sugar-protein cocrystals. The capability of comprehensive sugar libraries in providing key insights in glycan-ligand interaction is, thus, highlighted.

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Reviews citing this publication (11)

  1. Heparan sulfate and heparin interactions with proteins. Meneghetti MC, Hughes AJ, Rudd TR, Nader HB, Powell AK, Yates EA, Lima MA. J R Soc Interface 12 0589 (2015)
  2. Heparin Mimetics: Their Therapeutic Potential. Mohamed S, Coombe DR. Pharmaceuticals (Basel) 10 E78 (2017)
  3. Current structural biology of the heparin interactome. Pomin VH, Mulloy B. Curr Opin Struct Biol 34 17-25 (2015)
  4. Synthetic heparin and heparan sulfate oligosaccharides and their protein interactions. Zulueta MM, Lin SY, Hu YP, Hung SC. Curr Opin Chem Biol 17 1023-1029 (2013)
  5. Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly. Pawar NJ, Wang L, Higo T, Bhattacharya C, Kancharla PK, Zhang F, Baryal K, Huo CX, Liu J, Linhardt RJ, Huang X, Hsieh-Wilson LC. Angew Chem Int Ed Engl 58 18577-18583 (2019)
  6. Sulfated Alginates as Heparin Analogues: A Review of Chemical and Functional Properties. Arlov Ø, Skjåk-Bræk G. Molecules 22 E778 (2017)
  7. Can we produce heparin/heparan sulfate biomimetics using "mother-nature" as the gold standard? Farrugia BL, Lord MS, Melrose J, Whitelock JM. Molecules 20 4254-4276 (2015)
  8. Synthetic Oligosaccharide Libraries and Microarray Technology: A Powerful Combination for the Success of Current Glycosaminoglycan Interactomics. Pomin VH, Wang X. ChemMedChem 13 648-661 (2018)
  9. Synthetic probes of glycosaminoglycan function. Griffin ME, Hsieh-Wilson LC. Curr Opin Chem Biol 17 1014-1022 (2013)
  10. NMR Characterization of the Interactions Between Glycosaminoglycans and Proteins. Bu C, Jin L. Front Mol Biosci 8 646808 (2021)
  11. Polymers Inspired by Heparin and Heparan Sulfate for Viral Targeting. Hoffmann M, Snyder NL, Hartmann L. Macromolecules 55 7957-7973 (2022)

Articles citing this publication (28)

  1. Heparan Sulfate Microarray Reveals That Heparan Sulfate-Protein Binding Exhibits Different Ligand Requirements. Zong C, Venot A, Li X, Lu W, Xiao W, Wilkes JL, Salanga CL, Handel TM, Wang L, Wolfert MA, Boons GJ. J Am Chem Soc 139 9534-9543 (2017)
  2. Tunable heparan sulfate mimetics for modulating chemokine activity. Sheng GJ, Oh YI, Chang SK, Hsieh-Wilson LC. J Am Chem Soc 135 10898-10901 (2013)
  3. Structural basis for oligomerization and glycosaminoglycan binding of CCL5 and CCL3. Liang WG, Triandafillou CG, Huang TY, Zulueta MM, Banerjee S, Banerjee S, Dinner AR, Hung SC, Tang WJ. Proc Natl Acad Sci U S A 113 5000-5005 (2016)
  4. Synthesis of the heparin-based anticoagulant drug fondaparinux. Chang CH, Lico LS, Huang TY, Lin SY, Chang CL, Arco SD, Hung SC. Angew Chem Int Ed Engl 53 9876-9879 (2014)
  5. Divergent Synthesis of Heparan Sulfate Oligosaccharides. Dulaney SB, Xu Y, Wang P, Tiruchinapally G, Wang Z, Kathawa J, El-Dakdouki MH, Yang B, Liu J, Huang X. J Org Chem 80 12265-12279 (2015)
  6. Making the longest sugars: a chemical synthesis of heparin-related [4] n oligosaccharides from 16-mer to 40-mer. Hansen SU, Miller GJ, Cliff MJ, Jayson GC, Gardiner JM. Chem Sci 6 6158-6164 (2015)
  7. Computational analysis of interactions in structurally available protein-glycosaminoglycan complexes. Samsonov SA, Pisabarro MT. Glycobiology 26 850-861 (2016)
  8. Functional and structural characterization of a heparanase. Bohlmann L, Tredwell GD, Yu X, Chang CW, Haselhorst T, Winger M, Dyason JC, Thomson RJ, Tiralongo J, Beacham IR, Blanchard H, von Itzstein M. Nat Chem Biol 11 955-957 (2015)
  9. Regioselective one-pot protection, protection-glycosylation and protection-glycosylation-glycosylation of carbohydrates: a case study with D-glucose. Huang TY, Zulueta MM, Hung SC. Org Biomol Chem 12 376-382 (2014)
  10. Sugar Silanes: Versatile Reagents for Stereocontrolled Glycosylation via Intramolecular Aglycone Delivery. Walk JT, Buchan ZA, Montgomery J. Chem Sci 6 3448-3453 (2015)
  11. Development and application of site mapping methods for the design of glycosaminoglycans. Agostino M, Gandhi NS, Mancera RL. Glycobiology 24 840-851 (2014)
  12. Detection of mucopolysaccharidosis III-A (Sanfilippo Syndrome-A) in dried blood spots (DBS) by tandem mass spectrometry. Yi F, Hong X, Kumar AB, Zong C, Boons GJ, Scott CR, Turecek F, Robinson BH, Gelb MH. Mol Genet Metab 125 59-63 (2018)
  13. Fully Synthetic Heparan Sulfate-Based Neural Tissue Construct That Maintains the Undifferentiated State of Neural Stem Cells. Chopra P, Logun MT, White EM, Lu W, Locklin J, Karumbaiah L, Boons GJ. ACS Chem Biol 14 1921-1929 (2019)
  14. Synthesis of a heparin-related GlcN-IdoA sulfation-site variable disaccharide library and analysis by Raman and ROA spectroscopy. Miller GJ, Hansen SU, Baráth M, Johannessen C, Blanch EW, Jayson GC, Gardiner JM. Carbohydr Res 400 44-53 (2014)
  15. Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions. Yang W, Eken Y, Zhang J, Cole LE, Ramadan S, Xu Y, Zhang Z, Liu J, Wilson AK, Huang X. Chem Sci 11 6393-6404 (2020)
  16. Discovery of rare sulfated N-unsubstituted glucosamine based heparan sulfate analogs selectively activating chemokines. Jain P, Shanthamurthy CD, Leviatan Ben-Arye S, Woods RJ, Kikkeri R, Padler-Karavani V. Chem Sci 12 3674-3681 (2021)
  17. Modular synthesis of heparin-related tetra-, hexa- and octasaccharides with differential o-6 protections: programming for regiodefined 6-o-modifications. Baráth M, Hansen SU, Dalton CE, Jayson GC, Miller GJ, Gardiner JM. Molecules 20 6167-6180 (2015)
  18. Syntheses of sulfated glycopolymers and analyses of their BACE-1 inhibitory activity. Nishimura Y, Shudo H, Seto H, Hoshino Y, Miura Y. Bioorg Med Chem Lett 23 6390-6395 (2013)
  19. Effect of extension of the heparin binding pocket on the structure, stability, and cell proliferation activity of the human acidic fibroblast growth factor. Davis JE, Gundampati RK, Jayanthi S, Anderson J, Pickhardt A, Koppolu BP, Zaharoff DA, Kumar TKS. Biochem Biophys Rep 13 45-57 (2018)
  20. Expedient Synthesis of a Library of Heparan Sulfate-Like "Head-to-Tail" Linked Multimers for Structure and Activity Relationship Studies. Zhang J, Liang L, Yang W, Ramadan S, Baryal K, Huo CX, Bernard JJ, Liu J, Hsieh-Wilson L, Zhang F, Linhardt RJ, Huang X. Angew Chem Int Ed Engl 61 e202209730 (2022)
  21. Automated Solid Phase Assisted Synthesis of a Heparan Sulfate Disaccharide Library. Ramadan S, Su G, Baryal K, Hsieh-Wilson LC, Liu J, Huang X. Org Chem Front 9 2910-2920 (2022)
  22. Probing the role of proline -135 on the structure, stability, and cell proliferation activity of human acidic fibroblast growth factor. Davis JE, Alghanmi A, Gundampati RK, Jayanthi S, Fields E, Armstrong M, Weidling V, Shah V, Agrawal S, Koppolu BP, Zaharoff DA, Kumar TKS. Arch Biochem Biophys 654 115-125 (2018)
  23. Rational designing of glyco-nanovehicles to target cellular heterogeneity. Jain P, Shanthamurthy CD, Chaudhary PM, Kikkeri R. Chem Sci 12 4021-4027 (2021)
  24. Interactions between a Heparin Trisaccharide Library and FGF-1 Analyzed by NMR Methods. García-Jiménez MJ, Gil-Caballero S, Canales Á, Jiménez-Barbero J, de Paz JL, Nieto PM. Int J Mol Sci 18 E1293 (2017)
  25. Catalyst-free regioselective acetylation of primary hydroxy groups in partially protected and unprotected thioglycosides with acetic acid. Abronina PI, Malysheva NN, Zinin AI, Kolotyrkina NG, Stepanova EV, Kononov LO. RSC Adv 10 36836-36842 (2020)
  26. Heparan sulfate glycomimetics via iterative assembly of "clickable" disaccharides. Yang C, Deng Y, Wang Y, Xia C, Mehta AY, Baker KJ, Samal A, Booneimsri P, Lertmaneedang C, Hwang S, Flynn JP, Cao M, Liu C, Zhu AC, Cummings RD, Lin C, Mohanty U, Niu J. Chem Sci 14 3514-3522 (2023)
  27. Efficient platform for synthesizing comprehensive heparan sulfate oligosaccharide libraries for decoding glycosaminoglycan-protein interactions. Wang L, Sorum AW, Huang BS, Kern MK, Su G, Pawar N, Huang X, Liu J, Pohl NLB, Hsieh-Wilson LC. Nat Chem 15 1108-1117 (2023)
  28. Single-Step Per-O-Sulfonation of Sugar Oligomers with Concomitant 1,6-Anhydro Bridge Formation for Binding Fibroblast Growth Factors. Yeh CJ, Ku CC, Lin WC, Fan CY, Zulueta MML, Manabe Y, Fukase K, Li YK, Hung SC. Chembiochem 20 237-240 (2019)


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