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Artificial Multivalent Sugar Ligands to Understand and Manipulate Carbohydrate-Protein Interactions

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Host-Guest Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 218))

Abstract

Multivalency plays an important functional role in carbohydrate-protein interactions. Understanding of the molecular principles underlying multivalency effects is an important goal of biological chemistry. Consequently, a large number of different synthetic mulitvalent glycoligands have been designed to interfere effectively with carbohydrate-protein interactions and to facilitate the investigation of the multiple interactions occurring during these molecular recognition events. Control of inflammation processes and of microbial adhesion are important examples where multivalent carbohydrate ligands might be developed into useful therapeutics such as in the context of an anti-adhesion therapy. Furthermore, cell-cell interactions can also be manipulated by a chemical bioengineering approach which utilizes synthetic substrates in the biosynthetic pathways leading to the assembly of the complex carbohydrate environment on cell surfaces.

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7 References

  1. Kiessling LL, Gestwicki JE, Strong LE (2000) Curr Opin Chem Biol 4:696

    CAS  Google Scholar 

  2. Varki A, Cummings R, Esko J, Freeze H, Hart G, Marth J (eds) (1999) Essentials of Glycobiology. Cold Spring Harbor Laboratory Press, La Jolla

    Google Scholar 

  3. Bertozzi CR, Kiessling LL (2001) Science 291:2357

    CAS  Google Scholar 

  4. Karlsson K-A (1995) Curr Opin Struct Biol 5:6221

    Google Scholar 

  5. Lis H, Sharon N (1998) Chem Rev 98:637

    CAS  Google Scholar 

  6. Varki A (1993) Glycobiology 3:97

    CAS  Google Scholar 

  7. Kobata A (1993) Acc Chem Res 26:319

    CAS  Google Scholar 

  8. Dwek RA (1996) Chem Rev 96:663

    Google Scholar 

  9. Rudd PM, Elliott T, Cresswell P, Wilson IA, Dwek RA (2001) Science 291:2370

    CAS  Google Scholar 

  10. Mammen M, Choi SK, Whitesides GM (1998) Angew Chem 110:2908; Angew Chem Int Ed 37:2754

    Google Scholar 

  11. Sears P, Wong C-H (1999) Angew Chem 111:2446; Angew Chem Int Ed 38:2300

    Google Scholar 

  12. Toone EJ (1994) Curr Opin Struct Biol 4:719

    CAS  Google Scholar 

  13. Kiessling LL, Pohl NL (1996) Chem Biol 3:71

    CAS  Google Scholar 

  14. Burkhalter NF, Dimick SM, Toone EJ (2000) In: Ernst B, Hart GW, Sinaï P (eds) Carbohydrates in Chemistry and Biology 2:863

    Google Scholar 

  15. Lee YC (1978) Carbohydr Res 67:509

    CAS  Google Scholar 

  16. Lee RT, Lee YC (1987) Glycoconjugate J 4:317

    CAS  Google Scholar 

  17. Lee RT, Lin P, Lee YC (1984) Biochemistry 23:4255

    CAS  Google Scholar 

  18. Lee YC, Lee RT (1995) Acc Chem Res 28:321

    CAS  Google Scholar 

  19. Connolly T, Townsend RR, Kawaguchi K, Bell WR, Lee YC (1982) J Biol Chem 257:939

    CAS  Google Scholar 

  20. Kiessling LL, String LE, Gestwicki JE (2000) Annu Rep Med Chem 35:321

    CAS  Google Scholar 

  21. Lindhorst TK (1996) Nachr Chem Tech Lab 44:1073

    CAS  Google Scholar 

  22. Sears P, Wong C-H (1998) Chem Commun:1161

    Google Scholar 

  23. Jayaraman N, Nepogodiev SA, Stoddart JF (1997) Chem Eur J 3:1193

    CAS  Google Scholar 

  24. Zistler A, Koch S, Schlüter AD (1999) J Chem Soc, Perkin Trans 1:501

    Google Scholar 

  25. Sliedregt LAJM, Rensen PCN, Rump ET, van Santbrink PJ, Bijsterbosch MK, Valentijn ARPM, van der Marel GA, van Boom JH, vam Berkel TJC, Biessen EAL (1999) J Med Chem 42:609

    CAS  Google Scholar 

  26. Lindhorst TK, Kieburg C (1996) Angew Chem 108:2083; Angew Chem Int Ed Engl 35:1953

    Google Scholar 

  27. Lindhorst TK, Dubber M, Krallmann-Wenzel U, Ehlers S (2000) Eur J Org Chem:2027

    Google Scholar 

  28. Langer P, Ince SJ, Ley SV 1998, J Chem Soc, Perkin Trans 1:3913

    Google Scholar 

  29. Lindhorst TK, Kötter S, Krallmann-Wenzel U, Ehlers S (2001) J Chem Soc, Perkin Trans 1:823

    Google Scholar 

  30. König B, Fricke T, Waßmann A, Krallmann-Wenzel U, Lindhorst TK (1998) Tetrahedron Lett 39:2307

    Google Scholar 

  31. Biessen EAL, Noorman F, van Teijlingen ME, Kuiper J, Barrett-Bergshoeff M, Bijsterbosch MK, Rijken DC, van Berkel TJC (1996) J Biol Chem 271:28024

    CAS  Google Scholar 

  32. Wittmann V, Seeberger S (2000) Angew Chem 112:4508; Angew Chem Int Ed 39:4348

    Google Scholar 

  33. Dubber M, Lindhorst TK (1998) Carbohydr Res 310:350

    Google Scholar 

  34. Dubber M, Lindhorst TK (2000) J Org Chem 65:5275

    CAS  Google Scholar 

  35. Patel A, Lindhorst TK (2000) J Org Chem 66:2674

    Google Scholar 

  36. Spevak W, Foxall C, Charych DH, Dasgupta F, Nagy JO (1996) J Med Chem 39:1018

    CAS  Google Scholar 

  37. Spevak W, Nagy JO, Charych DH, Schaefer ME, Gilbert JH (1993) J Am Chem Soc 115: 1146

    CAS  Google Scholar 

  38. Kingery-Wood JE, Williams KW, Sigal GB Whitesides GM (1992) J Am Chem Soc 114:7303

    CAS  Google Scholar 

  39. Spevak W, Nagy JO, Charych DH, Schaefer ME, Gilbert JH, Bednarski MD (1993) J Am Chem Soc 115:1146

    CAS  Google Scholar 

  40. Bovin NV, Gabius JH (1995) Chem Soc Rev:413

    Google Scholar 

  41. Roy R (1996) TIGG 8:79

    Google Scholar 

  42. Roy R (1996) In: Khan SH, O’Neill RA (eds) Modern Methods in Carbohydrate Synthesis. Harwood Academic Publishers, Amsterdam, p 378

    Google Scholar 

  43. Kobayashi K, Akaike T, Usui T (1994) Methods Enzymol 242:226

    CAS  Google Scholar 

  44. Lee RT, Lee YC (1974) Carbohydr Res 34:151

    CAS  Google Scholar 

  45. Lee RT Lee YC (1982) Methods Enzymol 83:299

    CAS  Google Scholar 

  46. Roy R, Laferriére CA (1988) Carbohydr Res 177:C1

    CAS  Google Scholar 

  47. Roy R, Andersson FO, Harms G, Kelm S, Schauer R (1992) Angew Chem 104:1551; Angew Chem Int Ed Engl 31:1478

    CAS  Google Scholar 

  48. Roy R, Park WK, Srivastava OM, Foxall LV (1996) Bioorg Med Chem Lett 6:1399

    CAS  Google Scholar 

  49. Byramova NE, Mochalova LV, Belyanchikov IM, Matrosovich MN, Bovin NV (1991) J Carbohydr Res 10:691

    CAS  Google Scholar 

  50. Chernyak AY, Kononov LO, Kochetkov NK (1994) J Carbohydr Res 13:383

    CAS  Google Scholar 

  51. Lees WJ, Spaltenstein A, Kingery-Wood JE, Whitesides GM (1994) J Med Chem 37: 3419

    CAS  Google Scholar 

  52. Mammen M, Dahmann G, Whitesides GM (1995) J Med Chem 38:4179

    CAS  Google Scholar 

  53. Sallas F, Nishimura S-I (2000) J Chem Soc, Perkin Trans 1:2091

    Google Scholar 

  54. Thoma G, Magnani J, Öhrlein R, Ernst B, Schwarzenbach F, Duthaler RO (1997) J Am Chem Soc 119:7414

    CAS  Google Scholar 

  55. Thoma G, Patton JT, Magnani JL, Ernst B, Öhrlein R, Duthaler RO (1999) J Am Chem Soc 121:5919

    CAS  Google Scholar 

  56. Fraser C, Grubbs RH (1995) Macromolecules 28:7248

    CAS  Google Scholar 

  57. Lynn DM, Kanaoka S, Grubbs RH (1996) J Am Chem Soc 118:784

    CAS  Google Scholar 

  58. Dias EL, Nguyen ST, Grubbs RH (1997) J Am Chem Soc 119:3887

    CAS  Google Scholar 

  59. Nomura K, Schrock RR (1996) Macromolecules 29:540

    CAS  Google Scholar 

  60. Gordon EJ, Sanders WJ, Kiessling LL (1998) Nature 392:30

    CAS  Google Scholar 

  61. Mann DA, Kanai M, Maly DJ, Kiessling LL (1998) J Am Chem Soc 120:10575

    CAS  Google Scholar 

  62. Pohl NL, Kiessling LL (1999) Synthesis SI:1515

    Google Scholar 

  63. Strong LE, Kiessling LL (1999) J Am Chem Soc 121:6193

    CAS  Google Scholar 

  64. Roy R (1997) In: Driguez H, Thiem J (eds) Top Curr Chem 187:Glycoscience, Synthesis of Substrate Analogs and Mimetics, p 241

    Google Scholar 

  65. Roy R (1996) Curr Opin Struct Biol 6:692

    CAS  Google Scholar 

  66. Roy R (1999) Carbohydr Eur 27:34

    Google Scholar 

  67. Zanini D, Roy R (1998) Architectonic Neoglycoconjugates: Effects of Shapes and Valencies in Multiple Carbohydrate-Protein Interactions. In: Chapleur Y (ed) Carbohydrate Mimics, Concepts and Methods. Wiley-VCH, Weinheim, p 385

    Google Scholar 

  68. Lindhorst TK (2001) In: Vögtle F (ed) Top Curr Chem:Dendrimers IV, in press

    Google Scholar 

  69. Sadalapure K, Lindhorst TK (2000) Angew Chem 112:2066; Angew Chem Int Ed 39:20

    Google Scholar 

  70. Roy R, Kim JM (1999) Angew Chem 111:380; Angew Chem Int Ed 38:369

    Google Scholar 

  71. Roy R, Das SK, Santoyo-González F, Hernández-Mateo F, Dam TK, Brewer CF (2000) Chem Eur J 6:1757

    CAS  Google Scholar 

  72. Dondoni A, Marra A, Scherrmann M-C, Casnati A, Sansone F, Ungaro R (1997) Chem Eur J 3:1774

    CAS  Google Scholar 

  73. Ortiz-Mellet C, Benito JM, García Fernández JM, Law H, Chmurski K, Defaye J, O’Sullivan ML, Caro HN (1998) Chem Eur J 4:2523

    CAS  Google Scholar 

  74. Stoll MS, Hounsell EF, Lawson AM, Chai W, Feizi T (1990) Eur J Biochem 189:499

    CAS  Google Scholar 

  75. Mrksich M (2000) Chem Soc Rev 29:267

    CAS  Google Scholar 

  76. Mrksich M (2001) this issue of Top Curr Chem

    Google Scholar 

  77. Aronson M et al. (1979) J Infect Dis 139:329

    CAS  Google Scholar 

  78. Mammen M, Dahmann G, Whitesides GM (1995) J Med Chem 38:4179

    CAS  Google Scholar 

  79. Sabesan S, Duus Jø, Domaille P, Kelm S, Paulson JC (1991) J Am Chem Soc 113:5865

    CAS  Google Scholar 

  80. Glick GD, Knowles JR (1991) J Am Chem Soc 113:4701

    CAS  Google Scholar 

  81. Kamitakahara H, Suzuki T, Nishigori N, Suzuki Y, Kanie O, Wong C-H (1998) Angew Chem 110:1611; Angew Chem Int Ed 37:1524

    Google Scholar 

  82. Tomalia DA, Esfand R (1997) Chem Ind 416

    Google Scholar 

  83. Reuter JD, Myc A, Hayes MM, Gan Z, Roy R, Qin D, Yin R, Piehler LT, Esfand R, Tomalia DA, Baker JR, Jr (1999) Bioconj Chem 10:271

    CAS  Google Scholar 

  84. Cines DB, Pollak ES, Buck CA, Loscalzo J, Zimmermann GA, McEver RP, Pober JS, Wick TM, Konkle BA, Schwartz BS, Barnathan ES, McCrae KR, Hug BA, Schmidt A-M, Stern DM (1998) Blood, 91:3527

    CAS  Google Scholar 

  85. Varki A (1994) Proc Nat Acad Sci USA 91:7390

    CAS  Google Scholar 

  86. Thoma G, Magnani JL, Patton JT, Ernst B, Jahnke W (2001) Angew Chem 113:1995; Angew Chem Int Ed 40:1941

    Google Scholar 

  87. Simanek EE, McGarvey GJ, Jablonski JA, Wong C-H (1998) Chem Rev 98:833

    CAS  Google Scholar 

  88. Bertozzi CR (1995) Chem Biol 2:703

    CAS  Google Scholar 

  89. Kretzschmar G, Sprengard U, Kunz H, Bartnik E, Schmidt W, Toepfer A, Hörsch B, Krause M, Seiffge D (1995) Tetrahedron 51:13015, 86

    CAS  Google Scholar 

  90. Gordon EJ, Strong LE, Kiessling LL (1998) Bioorg Med Chem Lett 6:1293

    CAS  Google Scholar 

  91. Bray D, Levin MD, Morton-Firth CJ (1998) Nature 393:85

    CAS  Google Scholar 

  92. Liu Y, Levit M, Lurz R, Surette MG, Stock JB (1997) EMBO J 16:7231

    CAS  Google Scholar 

  93. Gestwicki JE, Strong LE, Kiessling LL (2000) Chem Biol 7:583

    CAS  Google Scholar 

  94. Roy R, Zanini D, Meunier SJ, Romanowska A (1993) J Chem Soc, Chem Commun:1896

    Google Scholar 

  95. Roy R, Park WKC, Zanini D, Foxall C, Srivastava OP (1997) Carbohydr Lett 2:259

    CAS  Google Scholar 

  96. Ashton PR, Hounsell EF, Jayaraman N, Nilsen TM, Spencer N, Stoddart JF (1998) J Org Chem 63:3429

    CAS  Google Scholar 

  97. Roy R, Pagé D, Perez S F, Bencomo VV (1998) Glycoconjugate J 15:251

    CAS  Google Scholar 

  98. Roy R, Baek MG, Xia Z, Rittenhouse-Diakun K (1999) Glycoconjugate J 16:S53

    Google Scholar 

  99. Zanini D, Roy R (1998) J Org Chem 63:3486

    CAS  Google Scholar 

  100. Sharon N (1987) FEBS Lett 217:145

    CAS  Google Scholar 

  101. Connell H, Agace W, Klemm P, Schembri M, M?rlid S, Svanborg C (1996) Proc Natl Acad Sci USA 93:9827

    CAS  Google Scholar 

  102. Struve C, Krogfelt KA (1999) Microbiology 145:2683

    CAS  Google Scholar 

  103. Firon N, Ofek I, Sharon N (1983) Carbohydr Res 120:235

    CAS  Google Scholar 

  104. Neeser J-R, Koellreutter B, Wuersch P (1986) Infect Immun 52:428

    CAS  Google Scholar 

  105. Firon N, Ashkenazi S, Mirleman D, Ofek I, Sharon N (1987) Infect Immun 55:472

    CAS  Google Scholar 

  106. Klemm P, Jørgensen, van Die I, de Ree H, Bergmans H (1985) Mol Gen Genet 199:410

    CAS  Google Scholar 

  107. Lindhorst TK, Kieburg C, Krallmann-Wenzel U (1998) Glycoconjugate J 15:605

    CAS  Google Scholar 

  108. Choudhury D, Thompson A, Stojanoff V, Langermann S, Pinkner J, Hultgreen SJ, Knight SD (1999) Science 285:1061

    CAS  Google Scholar 

  109. Sauer FG, Barnhart M, Choudhury D, Knight SD, Waksman G, Hultgren SJ (2000) Curr Opin Struct Biol 10:548

    CAS  Google Scholar 

  110. Knight SD, Berglund J, Choudhury D (2000) Curr Opin Chem Biol 4:653

    CAS  Google Scholar 

  111. Hansen HC, Haataja S, Finne J, Magnusson G (1997) J Am Chem Soc 119:6974

    CAS  Google Scholar 

  112. Lindberg AA, Brown JE, Stromberg N, Westling-Ryd M, Schultz JE, Karlsson KA (1987) J Biol Chem 262:1779

    CAS  Google Scholar 

  113. Merrit EA, Hol WGJ (1995) Curr Opin Struct Biol 5:165

    Google Scholar 

  114. Merrit EA, Sarfaty S, Feil IK, Hol WGJ (1997) Structure 5:1485

    Google Scholar 

  115. Fan E, Zhang Z, Minke WE, Hou Z, Verlinde CLMJ, Hol WGJ (2000) J Am Chem Soc 122:2663

    CAS  Google Scholar 

  116. Kitov PI, Sadowska JM, Mulvey G, Armstrong GD, Ling H, Pannu NS, Read RJ, Bundle DR (2000) Nature 403:669

    CAS  Google Scholar 

  117. Fan E, Merritt EA, Verlinde CLMJ, Hol WGJ (2000) Curr Opin Struct Biol 10:680

    CAS  Google Scholar 

  118. Ling H, Boodhoo A, Hazes B, Cummings MD, Armstrong GD, Brunton JL, Read RJ (1998) Biochemistry 37:1777

    CAS  Google Scholar 

  119. Seeberger PH, Haase W-C (2000) Chem Rev 100:4349

    CAS  Google Scholar 

  120. Sears P, Wong C-H (2001) Science 291:2344

    CAS  Google Scholar 

  121. Vliegenthart JFG, Montreuil J (1995) In: Montreuil J, Vliegenthart JFG, Schachter H (eds) Glycoproteins, New Compr Biochem, 29a:p 13

    Google Scholar 

  122. Kayser H, Zeitler R, Kannicht C, Grunow D, Nuck R, Reutter W (1992) J Biol Chem 267:16934

    CAS  Google Scholar 

  123. Keppler OT, Stehling P, Herrmann M, Kayser H, Grunow D, Reutter W, Pawlia M (1995) J Biol Chem 270:1308

    CAS  Google Scholar 

  124. Keppler OT, Horstkorte R, Pawlita M, Schmidt C, Reutter W (2001) Glycobiology 11:11R

    CAS  Google Scholar 

  125. Varki A (1991) FASEB J 5:226

    CAS  Google Scholar 

  126. Reutter W, Keppler O, Pawlita M, Schüler C, Horstkorte R, Schmidt C, Hoppe B, Lucka L, Stehling P, Mickeleit M, Biochemical Engineering by New N-Acylmannosamines of Sialic Acid Creates New Biological Characteristics and Technical Tools of its N-Acyl Side Chain. In Sialobiology and other forms of glycosylation (1999) Inoue Y, Lee YC, Fat I (eds). Osaka: Gakushin Publishing Company, pp 281

    Google Scholar 

  127. Mahal LK, Yarema KJ, Bertozzi CR (1997) Science 276:1125

    CAS  Google Scholar 

  128. Saxon E, Bertozzi CR (2000) Science 287:2007

    CAS  Google Scholar 

  129. Staudinger H, Meyer J (1919) Helv Chim Acta 2:635

    CAS  Google Scholar 

  130. Gololobov YG, Kasukhin LF (1992) Tetrahedron 48:1353

    CAS  Google Scholar 

  131. Yarema KJ, Mahal LK, Bruehl RE, Rodriguez EC, Bertozzi CR (1998) J Biol Chem 273: 31168

    CAS  Google Scholar 

  132. Lemieux GA, Yarema KJ, Jacobs CL, Bertozzi CR (1999) J Am Chem Soc 121:4278

    CAS  Google Scholar 

  133. Lee JH, Baker TJ, Mahal LK, Zabner J, Bertozzi CR, Wierner DF, Welsh MJ (1999) J Biol Chem 274:21878

    CAS  Google Scholar 

  134. Schmidt C, Ohlemeyer C, Kettenmann H, Reutter W, Horstkorte R (2000) FEBS Lett 478:276

    CAS  Google Scholar 

  135. Lohof E, Planker E, Mang C, Burkhart F, Dechantsreiter MA, Haubner R, Wester H-J, Schwaiger M, Hölzemann G, Goodman SL, Kessler H (2000) Angew Chem 112:2868; Angew Chem Int Ed 39:2761

    Google Scholar 

  136. Kessler H (1982) Angew Chem 94:509; Angew Chem Int Ed Engl 21:512

    CAS  Google Scholar 

  137. Breslow R, Belvedere S, Gershell L, Leung D (2000) Pure Appl Chem 72:333

    CAS  Google Scholar 

  138. Dimick SM, Powell SC, McMahon SA, Moothoo DN, Naismith JH, Toone EJ (1999) J Am Chem Soc 121:10286

    CAS  Google Scholar 

Download references

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  1. Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Otto-Hahn-Platz 4, 24098, Kiel, Germany

    Thisbe K. Lindhorst

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  1. Instituto de Investigaciones Químicas, Consejo Superior Investigaciones Cientificas, CSIC, Isla de la Cartuja, 41092, Sevilla, Spain

    Soledad Penadés

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Lindhorst, T.K. (2002). Artificial Multivalent Sugar Ligands to Understand and Manipulate Carbohydrate-Protein Interactions. In: Penadés, S. (eds) Host-Guest Chemistry. Topics in Current Chemistry, vol 218. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-45010-6_7

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