Skip to main content
SpringerLink
Log in

Chemical Synthesis of Glycopeptides

  • Chapter
  • First Online:
Glycopeptides and Glycoproteins

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 267))

Abstract

Despite its omnipresence in nature, comparatively little is known about how glycosylation affects the function and activity of proteins. To understand the role of protein glycosylation at the molecular level, it is important to have access to homogeneous glycoproteins and glycopeptides. Chemical synthesis is particularly suited to provide uniform glycoprotein material, thus playing a pivotal role for the advancement of glycobiology. This chapter summarizes the recent progress achieved in glycopeptide synthesis including new glycosylation methods, enzymatic transformations, chemoselective ligation and recombinant expression.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

Ac:

Acetyl

Acm:

Acetamidomethyl

Aloc:

Allyloxycarbonyl

Bn, Bzl:

Benzyl

Boc:

tert-Butyloxycarbonyl

Bu:

Butyl

BSA:

Bovine serum albumin

CLEAR:

Cross-linked ethoxylate acrylate resin

CMP:

Cytidine monophosphate

DCC:

Dicyclohexylcarbodiimide

DCM:

Dichloromethane, methylene chloride

DIEA, DIPEA:

N,N-Diisopropylethylamine

DMAP:

4-Dimethylaminopyridine

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

DTT:

Dithiothreitol

EDC, EDCI:

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

EDT:

Ethane-1,2-dithiol

Fmoc:

9-Fluorenylmethoxycarbonyl

Gdm:

Guanidinium

GDP:

Guanosine diphosphate

HATU:

2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

HBTU:

2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

HEPES:

4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid

HMPA:

4-Hydroxymethylphenoxyacetyl

HMPB:

4-(4-Hydroxymethyl-3-methoxyphenoxy)butyryl

HOBt:

N-Hydroxybenzotriazole

HYCRON:

Hydroxycrotyloligoethylene glycol-n-alkanoyl

ivDde:

(4,4-Dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl

MCA:

Monochloroacetyl

MES-Na:

Sodium mercaptoethanesulfonate

MOPS:

3-(N-Morpholino)propanesulfonic acid

NIS:

N-Iodosuccinimide

NMP:

N-Methylpyrrolidone

P i :

Phosphate

Pbf:

2,2,4,6,7-Pentamethyldihydrobenzofuran-5-sulfonyl

Phth:

Phthaloyl

PTSA:

p-Toluenesulfonic acid

PyBOP:

Benzotriazole-1-yl-tris-pyrrolidino-phosphonium hexafluorophosphate

SASRIN:

Super acid sensitve resin

Su:

Succinimidyl

TBAF:

Tetrabutylammonium fluoride

TBS:

tert-Butyldimethylsilyl

TCEP:

Tris(2-carboxyethyl)phosphine

Tf:

Trifluoromethanesulfonyl

TFA:

Trifluoroacetic acid

TFE:

Trifluoro ethanol

TfOH:

Trifluoromethanesulfonic acid

THF:

Tetrahydrofuran

TIS:

Triisopropylsilane

TMS:

Trimethylsilyl

Tris:

Tris(hydroxymethyl)aminomethane

Troc:

2,2,2-Trichloroethoxycarbonyl

Trt:

Trityl

Tsoc:

Triisopropylsilyloxycarbonyl

Z:

Benzyloxycarbonyl

References

  1. Seitz O (2000) ChemBioChem 1:215

    Google Scholar 

  2. Seitz O, Heinemann I, Mattes A, Waldmann H (2001) Tetrahedron 57:2247

    CAS  Google Scholar 

  3. Brocke C, Kunz H (2002) Bioorg Med Chem 10:3085

    CAS  Google Scholar 

  4. Grogan MJ, Pratt MR, Marcaurelle LA, Bertozzi CR (2002) Annu Rev Biochem 71:593

    CAS  Google Scholar 

  5. Hanson S, Best M, Bryan MC, Wong CH (2004) Trends Biochem Sci 29:656

    CAS  Google Scholar 

  6. Holeman A, Seeberger PH (2004) Curr Opin Biotechnol 15:615

    Google Scholar 

  7. Hang HC, Bertozzi CR (2005) Bioorg Med Chem 13:5021

    CAS  Google Scholar 

  8. Kajihara Y, Yamamoto N, Miyazaki T, Sato H (2005) Curr Med Chem 12:527

    CAS  Google Scholar 

  9. Pratt MR, Bertozzi CR (2005) Chem Soc Rev 34:58

    CAS  Google Scholar 

  10. Wong C-H (2005) J Org Chem 70:4219

    CAS  Google Scholar 

  11. Butler WT, Cunningh LW (1966) J Biol Chem 241:3882

    CAS  Google Scholar 

  12. Lamport DTA (1967) Nature 216:1322

    CAS  Google Scholar 

  13. Rodriguez IR, Whelan WJ (1985) Biochem Biophys Res Commun 132:829

    CAS  Google Scholar 

  14. Hofsteenge J, Müller DR, Debeer T, Löffler A, Richter WJ, Vliegenthart JFG (1994) Biochemistry 33:13524

    CAS  Google Scholar 

  15. Hart GW, Brew K, Grant GA, Bradshaw RA, Lennarz WJ (1979) J Biol Chem 254:9747

    CAS  Google Scholar 

  16. Zachara NE, Hart GW (2002) Chem Rev 102:431

    CAS  Google Scholar 

  17. Wells L, Vosseller K, Hart GW (2001) Science 291:2376

    CAS  Google Scholar 

  18. Spiro RG (1967) J Biol Chem 242:4813

    CAS  Google Scholar 

  19. Hart GW (1997) Annu Rev Biochem 66:315

    CAS  Google Scholar 

  20. Vliegenthart JFG, Casset F (1998) Curr Opin Struct Biol 8:565

    CAS  Google Scholar 

  21. Endo T (1999) Biochim Biophys Acta, Gen Subj 1473:237

    CAS  Google Scholar 

  22. Haltiwanger RS (2002) Curr Opin Struct Biol 12:593

    CAS  Google Scholar 

  23. Haines N, Irvine KD (2003) Nat Rev Mol Cell Biol 4:786

    CAS  Google Scholar 

  24. Shao L, Haltiwanger RS (2003) Cell Mol Life Sci 60:241

    CAS  Google Scholar 

  25. Upreti RK, Kumar M, Shankar V (2003) Proteomics 3:363

    CAS  Google Scholar 

  26. Lomako J, Lomako WM, Whelan WJ (2004) Biochim Biophys Acta, Gen Subj 1673:45

    CAS  Google Scholar 

  27. Szymanski CM, Wren BW (2005) Nat Rev Microbiol 3:225

    CAS  Google Scholar 

  28. Helenius A, Aebi M (2001) Science 291:2364

    CAS  Google Scholar 

  29. Cannon KS, Helenius A (1999) J Biol Chem 274:7537

    CAS  Google Scholar 

  30. Huppa JB, Ploegh HL (1998) Cell 92:145

    CAS  Google Scholar 

  31. Hammond C, Braakman I, Helenius A (1994) Proc Natl Acad Sci USA 91:913

    CAS  Google Scholar 

  32. Fukuda MN, Sasaki H, Lopez L, Fukuda M (1989) Blood 73:84

    CAS  Google Scholar 

  33. Wyss DF, Choi JS, Li J, Knoppers MH, Willis KJ, Arulanandam ARN, Smolyar A, Reinherz EL, Wagner G (1995) Science 269:1273

    CAS  Google Scholar 

  34. Szymanski CM, Burr DH, Guerry P (2002) Infect Immun 70:2242

    CAS  Google Scholar 

  35. Larsen JC, Szymanski C, Guerry P (2004) J Bacteriol 186:6508

    CAS  Google Scholar 

  36. Arora SK, Neely AN, Blair B, Lory S, Ramphal R (2005) Infect Immun 73:4395

    CAS  Google Scholar 

  37. Tanaka S, Meiselman HHJ, Engel E, Guth PH, Furukawa O, Wenby RB, Lee J, Kaunitz JD (2002) Dig Dis Sci 47:967

    CAS  Google Scholar 

  38. Fujita T, Ohara S, Sugaya T, Saigenji K, Hotta K (2000) Comp Biochem Physiol B Biochem Mol Biol 126:353

    CAS  Google Scholar 

  39. Cao XX, Bansil R, Bhaskar KR, Turner BS, LaMont JT, Niu N, Afdhal NH (1999) Biophys J 76:1250

    Article  CAS  Google Scholar 

  40. Tanaka S, Podolsky DK, Engel E, Guth PH, Kaunitz JD (1997) Am J Physiol, Gastroint Liver Physiol 276:G1473

    Google Scholar 

  41. Nordman H, Davies JR, Lindell G, Carlstedt I (1995) Biochem Soc Trans 23:S533

    Google Scholar 

  42. Ho SB, Roberton AM, Shekels LL, Lyftogt CT, Niehans GA, Toribara NW (1995) Gastroenterology 109:735

    CAS  Google Scholar 

  43. Bhaskar KR, Garik P, Turner BS, Bradley JD, Bansil R, Stanley HE, Lamont JT (1992) Nature 360:458

    CAS  Google Scholar 

  44. Jepson S, Komatsu M, Haq B, Arango ME, Huang DM, Carraway CAC, Carraway KL (2002) Oncogene 21:7524

    CAS  Google Scholar 

  45. McDermott KM, Crocker PR, Harris A, Burdick MD, Hinoda Y, Hayashi T, Imai K, Hollingsworth MA (2001) Int J Cancer 94:783

    CAS  Google Scholar 

  46. Hayashi T, Takahashi T, Motoya S, Ishida T, Itoh F, Adachi M, Hinoda Y, Imai K (2001) Digestion 63:87

    CAS  Google Scholar 

  47. Brinkman-Van der Linden ECM, Varki A (2000) J Biol Chem 275:8625

    CAS  Google Scholar 

  48. Borsig L, Wong R, Feramisco J, Nadeau DR, Varki NM, Varki A (2001) Proc Natl Acad Sci USA 98:3352

    CAS  Google Scholar 

  49. Nath D, Hartnell A, Happerfield L, Miles DW, Burchell J, Taylor-Papadimitriou J, Crocker PR (1999) Immunology 98:213

    CAS  Google Scholar 

  50. Kim YJ, Borsig L, Han HL, Varki NM, Varki A (1999) Am J Pathol 155:461

    CAS  Google Scholar 

  51. Chan AK, Lockhart DC, von Bernstorff W, Spanjaard RA, Joo HG, Eberlein TJ, Goedegebuure PS (1999) Int J Cancer 82:721

    CAS  Google Scholar 

  52. Komatsu M, Yee L, Carraway KL (1999) Cancer Res 59:2229

    CAS  Google Scholar 

  53. Agrawal B, Gendler SJ, Longenecker BM (1998) Mol Med Today 4:397

    CAS  Google Scholar 

  54. Agrawal B, Krantz MJ, Reddish MA, Longenecker BM (1998) Nat Med 4:43

    CAS  Google Scholar 

  55. Van de Wiel-van Kemenade E, Ligtenberg MJL, Deboer AJ, Buijs F, Vos HL, Melief CJM, Hilkens J, Figdor CG (1993) J Immunol 151:767

    CAS  Google Scholar 

  56. Lüttges J, Feyerabend B, Buchelt T, Pacena M, Kloppel G (2002) Am J Surg Pathol 26:466

    Google Scholar 

  57. Rahn JJ, Dabbagh L, Pasdar M, Hugh JC (2001) Cancer 91:1973

    CAS  Google Scholar 

  58. Kashiwagi H, Kijima H, Dowaki S, Ohtani Y, Tobita K, Tsukui M, Tanaka Y, Matsubayasi H, Tsuchida T, Yamazaki H, Nakamura M, Ueyama Y, Tanaka M, Tajima T, Makuuchi H (2000) Int J Oncol 16:455

    CAS  Google Scholar 

  59. Nitta T, Sugihara K, Tsuyama S, Murata F (2000) Cancer 88:245

    CAS  Google Scholar 

  60. Hiraga Y, Tanaka S, Haruma K, Yoshihara M, Sumii K, Kajiyama G, Shimamoto F, Kohno N (1998) Oncology 55:307

    CAS  Google Scholar 

  61. Kondo K, Kohno N, Yokoyama A, Hiwada K (1998) Cancer Res 58:2014

    CAS  Google Scholar 

  62. Spicer AP, Rowse GJ, Lidner TK, Gendler SJ (1995) J Biol Chem 270:30093

    CAS  Google Scholar 

  63. Nakamori S, Ota DM, Cleary KR, Shirotani K, Irimura T (1994) Gastroenterology 106:353

    CAS  Google Scholar 

  64. Ligtenberg MJL, Buijs F, Vos HL, Hilkens J (1992) Cancer Res 52:2318

    CAS  Google Scholar 

  65. Wesseling J, Van der Valk SW, Hilkens J (1996) Mol Biol Cell 7:565

    CAS  Google Scholar 

  66. Wesseling J, Van der Valk SW, Vos HL, Sonnenberg A, Hilkens J (1995) J Cell Biol 129:255

    CAS  Google Scholar 

  67. Guinez C, Morelle W, Michalski JC, Lefebvre T (2005) Int J Biochem Cell Biol 37:765

    CAS  Google Scholar 

  68. Whelan SA, Hart GW (2003) Circ Res 93:1047

    CAS  Google Scholar 

  69. Khidekel N, Hsieh-Wilson LC (2004) Org Biomol Chem 2:1

    CAS  Google Scholar 

  70. Wells L, Whalen SA, Hart GW (2003) Biochem Biophys Res Commun 302:435

    CAS  Google Scholar 

  71. Clark RS, Banerjee S, Coward JK (1990) J Org Chem 55:6275

    CAS  Google Scholar 

  72. Bolton CH, Jeanloz RW (1963) J Org Chem 28:3228

    CAS  Google Scholar 

  73. Szilagyi L, Gyorgydeak Z (1985) Carbohydr Res 143:21

    CAS  Google Scholar 

  74. Augé C, Gautheron C, Pora H (1989) Carbohydr Res 193:288

    Google Scholar 

  75. Sabesan S, Neira S (1992) Carbohydr Res 223:169

    CAS  Google Scholar 

  76. Tropper FD, Andersson FO, Braun S, Roy R (1992) Synthesis, p 618

    Google Scholar 

  77. Unverzagt C, Kunz H (1992) J Prakt Chem 334:570

    CAS  Google Scholar 

  78. Li C, Arasappan A, Fuchs PL (1993) Tetrahedron Lett 34:3535

    CAS  Google Scholar 

  79. Li C, Shih TL, Jeong JU, Arasappan A, Fuchs PL (1994) Tetrahedron Lett 35:2645

    CAS  Google Scholar 

  80. Matsubara K, Mukaiyama T (1994) Chem Lett:247

    Google Scholar 

  81. Soli ED, DeShong P (1999) J Org Chem 64:9724

    CAS  Google Scholar 

  82. McDonald FE, Danishefsky SJ (1992) J Org Chem 57:7001

    CAS  Google Scholar 

  83. Danishefsky SJ, Roberge JY (1995) Pure Appl Chem 67:1647

    CAS  Google Scholar 

  84. He Y, Hinklin RJ, Chang JY, Kiessling LL (2004) Org Lett 6:4479

    CAS  Google Scholar 

  85. Tanaka H, Iwata Y, Takahashi D, Adachi M, Takahashi T (2005) J Am Chem Soc 127:1630

    CAS  Google Scholar 

  86. Cohen-Anisfeld ST, Lansbury PT (1993) J Am Chem Soc 115:10531

    CAS  Google Scholar 

  87. Likhosherstov LM, Novikova OS, Derevitskaja VA, Kochetkov NK (1986) Carbohydr Res 146:C1

    CAS  Google Scholar 

  88. Likhosherstov LM, Novikova OS, Zheltova AO, Shibaev VN (2004) Russ Chem Bull 53:709

    CAS  Google Scholar 

  89. Likhosherstov LM, Novikova OS, Shibaev VN (2003) Dokl Chem 389:73

    CAS  Google Scholar 

  90. Likhosherstov LM, Novikova OS, Shibaev VN (2002) Dokl Chem 383:89

    CAS  Google Scholar 

  91. Bejugam M, Flitsch SL (2004) Org Lett 6:4001

    CAS  Google Scholar 

  92. Meinjohanns E, Meldal M, Paulsen H, Dwek RA, Bock K (1998) J Chem Soc, Perkin Trans 1:549

    Google Scholar 

  93. Hackenberger CPR, O'Reilly MK, Imperiali B (2005) J Org Chem 70:3574

    CAS  Google Scholar 

  94. Seko A, Koketsu M, Nishizono M, Enoki Y, Ibrahim HR, Juneja LR, Kim M, Yamamoto T (1997) Biochim Biophys Acta, Gen Subj 1335:23

    CAS  Google Scholar 

  95. Yamamoto N, Ohmori Y, Sakakibara T, Sasaki K, Juneja LR, Kajihara Y (2003) Angew Chem, Int Ed 42:2537

    CAS  Google Scholar 

  96. Kajihara Y, Suzuki Y, Yamamoto N, Sasaki K, Sakakibara T, Juneja LR (2004) Chem-Eur J 10:971

    CAS  Google Scholar 

  97. Fukae K, Yamamoto N, Hatakeyama Y, Kajihara Y (2004) Glycoconjugate J 21:243

    CAS  Google Scholar 

  98. Iijima H, Ogawa T (1989) Carbohydr Res 186:107

    CAS  Google Scholar 

  99. Paulsen H, Adermann K (1989) Liebigs Ann Chem:751

    Google Scholar 

  100. Bielfeldt T, Peters S, Meldal M, Bock K, Paulsen H (1992) Angew Chem, Int Ed Engl 31:857

    Google Scholar 

  101. Paulsen H, Peters S, Bielfeldt T, Meldal M, Bock K (1995) Carbohydr Res 268:17

    CAS  Google Scholar 

  102. Rio-Anneheim S, Paulsen H, Meldal M, Bock K (1995) J Chem Soc, Perkin Trans 1:1071

    Google Scholar 

  103. Vuljanic T, Bergquist KE, Clausen H, Roy S, Kihlberg J (1996) Tetrahedron 52:7983

    CAS  Google Scholar 

  104. Leuck M, Kunz H (1997) J Prakt Chem 339:322

    CAS  Google Scholar 

  105. Mathieux N, Paulsen H, Meldal M, Bock K (1997) J Chem Soc, Perkin Trans 1:2359

    Google Scholar 

  106. Sames D, Chen X-T, Danishefsky SJ (1997) Nature 389:587

    CAS  Google Scholar 

  107. Chen X-T, Danishefsky SJ, Sames D (1998) J Am Chem Soc 120:7760

    CAS  Google Scholar 

  108. Satyanarayana J, Gururaja TL, Naganagowda GA, Ramasubbu N, Levine MJ (1998) J Pept Res 52:165

    Article  CAS  Google Scholar 

  109. Schwarz JB, Kuduk SD, Chen X-T, Sames D, Glunz PW, Danishefsky SJ (1999) J Am Chem Soc 121:2662

    CAS  Google Scholar 

  110. Danishefsky SJ, Allen JR (2000) Angew Chem, Int Ed Engl 39:836

    CAS  Google Scholar 

  111. Kunz H, Birnbach S (1986) Angew Chem, Int Ed Engl 25:360

    Google Scholar 

  112. Paulsen H, Bielfeldt T, Peters S, Meldal M, Bock K (1994) Liebigs Ann Chem:369

    Google Scholar 

  113. Kuduk SD, Schwarz JB, Chen XT, Glunz PW, Sames D, Ragupathi G, Livingston PO, Danishefsky SJ (1998) J Am Chem Soc 120:12474

    CAS  Google Scholar 

  114. Liebe B, Kunz H (1997) Angew Chem, Int Ed Engl 36:618

    CAS  Google Scholar 

  115. Shao N, Guo Z (2005) Org Lett 7:3589

    CAS  Google Scholar 

  116. Lemieux RU, Ratcliffe RM (1979) Can J Chem 57:1244

    CAS  Google Scholar 

  117. Winterfeld GA, Ito Y, Ogawa T, Schmidt RR (1999) Eur J Org Chem:1167

    Google Scholar 

  118. Winterfeld GA, Schmidt RR (2001) Angew Chem, Int Ed 40:2654

    CAS  Google Scholar 

  119. Winterfeld GA, Khodair AI, Schmidt RR (2003) Eur J Org Chem:1009

    Google Scholar 

  120. Geiger J, Barroca N, Schmidt RR (2004) Synlett, p 836

    Google Scholar 

  121. Seitz O, Wong CH (1997) J Am Chem Soc 119:8766

    CAS  Google Scholar 

  122. Pohl T, Waldmann H (1997) J Am Chem Soc 119:6702

    CAS  Google Scholar 

  123. Salvador LA, Elofsson M, Kihlberg J (1995) Tetrahedron 51:5643

    CAS  Google Scholar 

  124. Arsequell G, Krippner L, Dwek RA, Wong SYC (1994) J Chem Soc, Chem Commun, p 2383

    Google Scholar 

  125. Elofsson M, Walse B, Kihlberg J (1991) Tetrahedron Lett 32:7613

    CAS  Google Scholar 

  126. Schultz M, Kunz H (1992) Tetrahedron Lett 33:5319

    CAS  Google Scholar 

  127. Vargas-Berenguel A, Meldal M, Paulsen H, Bock K (1994) J Chem Soc, Perkin Trans 1:2615

    Google Scholar 

  128. Meinjohanns E, Meldal M, Bock K (1995) Tetrahedron Lett 36:9205

    CAS  Google Scholar 

  129. Meinjohanns E, Vargas-Berenguel A, Meldal M, Paulsen H, Bock K (1995) J Chem Soc, Perkin Trans 1:2165

    Google Scholar 

  130. Jensen KJ, Hansen PR, Venugopal D, Barany G (1996) J Am Chem Soc 118:3148

    CAS  Google Scholar 

  131. Saha UK, Schmidt RR (1997) J Chem Soc, Perkin Trans 1:1855

    Google Scholar 

  132. Seibel R, Hillringhaus L, Moraru R (2005) Carbohydr Res 340:507

    CAS  Google Scholar 

  133. Wittmann V, Lennartz D (2002) Eur J Org Chem:1363

    Google Scholar 

  134. Wagner M, Dziadek S, Kunz H (2003) Chem-Eur J 9:6018

    CAS  Google Scholar 

  135. Dziadek S, Brocke C, Kunz H (2004) Chem-Eur J 10:4150

    CAS  Google Scholar 

  136. Reipen T, Kunz H (2003) Synthesis, p 2487

    Google Scholar 

  137. Brocke C, Kunz H (2003) Synlett, p 2052

    Google Scholar 

  138. Dziadek S, Kunz H (2003) Synlett, p 1623

    Google Scholar 

  139. Brocke C, Kunz H (2004) Synthesis, p 525

    Google Scholar 

  140. Adachi M, Tanaka H, Takahashi T (2004) Synlett, p 609

    Google Scholar 

  141. Tanaka H, Adachi M, Takahashi T (2005) Chem-Eur J 11:849

    CAS  Google Scholar 

  142. Blixt O, Allin K, Pereira L, Datta A, Paulson JC (2002) J Am Chem Soc 124:5739

    CAS  Google Scholar 

  143. Dudziak G, Bézay N, Schwientek T, Clausen H, Kunz H, Liese A (2000) Tetrahedron 56:5865

    CAS  Google Scholar 

  144. Bézay N, Dudziak G, Liese A, Kunz H (2001) Angew Chem, Int Ed 40:2292

    Google Scholar 

  145. Kunz H (2003) J Pept Sci 9:563

    CAS  Google Scholar 

  146. Cantacuzene D, Attal S, Bay S (1991) Bioorg Med Chem Lett 1:197

    CAS  Google Scholar 

  147. Cantacuzene D, Attal S (1991) Carbohydr Res 211:327

    CAS  Google Scholar 

  148. Nilsson KGI, Scigelova M (1994) Biotechnol Lett 16:671

    CAS  Google Scholar 

  149. Nilsson KGI, Ljunger G, Melin PM (1997) Biotechnol Lett 19:889

    CAS  Google Scholar 

  150. Varon D, Lioy E, Patarroyo ME, Schratt X, Unverzagt C (2002) Aust J Chem 55:161

    CAS  Google Scholar 

  151. Broddefalk J, Backlund J, Almqvist F, Johansson M, Holmdahl R, Kihlberg J (1998) J Am Chem Soc 120:7676

    CAS  Google Scholar 

  152. Broddefalk J, Forsgren M, Sethson I, Kihlberg J (1999) J Org Chem 64:8948

    CAS  Google Scholar 

  153. Holm B, Broddefalk J, Flodell S, Wellner E, Kihlberg J (2000) Tetrahedron 56:1579

    CAS  Google Scholar 

  154. Syed BM, Gustafsson T, Kihlberg J (2004) Tetrahedron 60:5571

    CAS  Google Scholar 

  155. Cudic M, Lauer-Fields JL, Fields GB (2005) J Pept Res 65:272

    CAS  Google Scholar 

  156. Marin J, Violette A, Briand JP, Guichard G (2004) Eur J Org Chem:3027

    Google Scholar 

  157. Bäcklund J, Treschow A, Bockermann R, Holm B, Holm L, Issazadeh-Navikas S, Kihlberg J, Holmdahl R (2002) Eur J Immunol 32:3776

    Google Scholar 

  158. Holm B, Bäcklund J, Recio MAF, Holmdahl R, Kihlberg J (2002) ChemBioChem 3:1209

    CAS  Google Scholar 

  159. Holm B, Baquer SM, Holm L, Holmdahl R, Kihlberg J (2003) Bioorg Med Chem 11:3981

    CAS  Google Scholar 

  160. Dzhambazov B, Holmdahl M, Yamada H, Lu SM, Vestberg M, Holm B, Johnell O, Kihlberg J, Holmdahl R (2005) Eur J Immunol 35:357

    CAS  Google Scholar 

  161. Holm L, Kjellen P, Holmdahl R, Kihlberg J (2005) Bioorg Med Chem 13:473

    CAS  Google Scholar 

  162. Leppänen A, White SP, Helin J, McEver RP, Cummings RD (2000) J Biol Chem 275:39569

    Google Scholar 

  163. Koeller KM, Smith MEB, Wong CH (2000) Bioorg Med Chem 8:1017

    CAS  Google Scholar 

  164. Koeller KM, Smith MEB, Huang RF, Wong CH (2000) J Am Chem Soc 122:4241

    CAS  Google Scholar 

  165. Koeller KM, Smith MEB, Wong CH (2000) J Am Chem Soc 122:742

    CAS  Google Scholar 

  166. Wang LX, Song HJ, Liu SW, Lu H, Jiang SB, Ni JH, Li HG (2005) ChemBioChem 6:1068

    CAS  Google Scholar 

  167. Singh S, Ni JH, Wang LX (2003) Bioorg Med Chem Lett 13:327

    CAS  Google Scholar 

  168. Li HG, Singh S, Zeng Y, Song HJ, Wang LX (2005) Bioorg Med Chem Lett 15:895

    CAS  Google Scholar 

  169. Fujita M, Shoda S, Haneda K, Inazu T, Takegawa K, Yamamoto K (2001) Biochim Biophys Acta, Gen Subj 1528:9

    CAS  Google Scholar 

  170. Li B, Zeng Y, Hauser S, Song H, Wang L-X (2005) J Am Chem Soc 127:9692

    CAS  Google Scholar 

  171. Witte K, Seitz O, Wong CH (1998) J Am Chem Soc 120:1979

    CAS  Google Scholar 

  172. Doores KJ, Davis BG (2005) Chem Commun, p 168

    Google Scholar 

  173. Wang ZG, Zhang XF, Visser M, Live D, Zatorski A, Iserloh U, Lloyd KO, Danishefsky SJ (2001) Angew Chem, Int Ed 40:1728

    CAS  Google Scholar 

  174. Dudkin VY, Miller JS, Danishefsky SJ (2003) Tetrahedron Lett 44:1791

    CAS  Google Scholar 

  175. Mandal M, Dudkin VY, Geng XD, Danishefsky S (2004) Angew Chem, Int Ed 43:2557

    CAS  Google Scholar 

  176. Geng XD, Dudkin VY, Mandal M, Danishefsky SJ (2004) Angew Chem, Int Ed 43:2562

    CAS  Google Scholar 

  177. Dudkin VY, Orlova M, Geng XD, Mandal M, Olson WC, Danishefsky SJ (2004) J Am Chem Soc 126:9560

    CAS  Google Scholar 

  178. Warren JD, Geng X, Danishefsky SJ (2006) Top Curr Chem, (in press)

    Google Scholar 

  179. Dawson PE, Muir TW, Clarklewis I, Kent SBH (1994) Science 266:776

    CAS  Google Scholar 

  180. Shin Y, Winans KA, Backes BJ, Kent SBH, Ellman JA, Bertozzi CR (1999) J Am Chem Soc 121:11684

    CAS  Google Scholar 

  181. Marcaurelle LA, Mizoue LS, Wilken J, Oldham L, Kent SBH, Handel TM, Bertozzi CR (2001) Chem-Eur J 7:1129

    CAS  Google Scholar 

  182. Dudkin VY, Miller JS, Danishefsky SJ (2004) J Am Chem Soc 126:736

    CAS  Google Scholar 

  183. Miller JS, Dudkin VY, Lyon GJ, Muir TW, Danishefsky SJ (2003) Angew Chem, Int Ed 42:431

    CAS  Google Scholar 

  184. Warren JD, Miller JS, Keding SJ, Danishefsky SJ (2004) J Am Chem Soc 126:6576

    CAS  Google Scholar 

  185. Tolbert TJ, Franke D, Wong CH (2005) Bioorg Med Chem 13:909

    CAS  Google Scholar 

  186. Hackenberger CPR, Friel CT, Radford SE, Imperiali B (2005) J Am Chem Soc 127:12882

    CAS  Google Scholar 

  187. Shao N, Xue J, Guo ZW (2003) J Org Chem 68:9003

    CAS  Google Scholar 

  188. Xue J, Guo ZW (2003) J Org Chem 68:2713

    CAS  Google Scholar 

  189. Wen S, Guo Z (2001) Org Lett 3:3773

    CAS  Google Scholar 

  190. Mizuno M, Goto K, Miura T (2005) Chem Lett 34:426

    CAS  Google Scholar 

  191. Glunz PW, Hintermann S, Williams LJ, Schwarz JB, Kuduk SD, Kudryashov V, Lloyd KO, Danishefsky SJ (2000) J Am Chem Soc 122:7273

    CAS  Google Scholar 

  192. Glunz PW, Hintermann S, Schwarz JB, Kuduk SD, Chen XT, Williams LJ, Sames D, Danishefsky SJ, Kudryashov V, Lloyd KO (1999) J Am Chem Soc 121:10636

    CAS  Google Scholar 

  193. Macmillan D, Bertozzi CR (2004) Angew Chem, Int Ed 43:1355

    CAS  Google Scholar 

  194. Macmillan D, Anderson DW (2004) Org Lett 6:4659

    CAS  Google Scholar 

  195. George SK, Schwientek T, Holm B, Reis CA, Clausen H, Kihlberg J (2001) J Am Chem Soc 123:11117

    CAS  Google Scholar 

  196. Izumi M, Shen G-J, Wacowich-Sgarbi S, Nakatani T, Plettenburg O, Wong C-H (2001) J Am Chem Soc 123:10909

    CAS  Google Scholar 

  197. Gutiérrez Gallego R, Kamerling JP, Vliegenthart JFG, Dudziak G, Kragl U, Wandrey C (2003) Biochimie 85:275

    Google Scholar 

  198. Teo CF, Hwang TS, Chen PH, Hung CH, Gao HS, Chang LS, Lin CH (2005) Adv Synth Catal 347:967

    CAS  Google Scholar 

  199. Wang SS (1973) J Am Chem Soc 95:1328

    CAS  Google Scholar 

  200. Sheppard RC, Williams BJ (1982) Int J Pept Protein Res 20:451

    Article  CAS  Google Scholar 

  201. Rink H (1987) Tetrahedron Lett 28:3787

    CAS  Google Scholar 

  202. Albericio F, Kneibcordonier N, Biancalana S, Gera L, Masada RI, Hudson D, Barany G (1990) J Org Chem 55:3730

    CAS  Google Scholar 

  203. Mergler M, Tanner R, Gosteli J, Grogg P (1988) Tetrahedron Lett 29:4005

    CAS  Google Scholar 

  204. Floersheimer A, Riniker B (1991) Pept. 1990, Proc Eur Pept Symp, 21st:131

    Google Scholar 

  205. Sieber P (1987) Tetrahedron Lett 28:2107

    CAS  Google Scholar 

  206. Barlos K, Gatos D, Kallitsis J, Papaphotiu G, Sotiriu P, Yao WQ, Schäfer W (1989) Tetrahedron Lett 30:3943

    CAS  Google Scholar 

  207. Seitz O, Kunz H (1995) Angew Chem, Int Ed Engl 34:803

    CAS  Google Scholar 

  208. Shao N, Xue B, Guo ZW (2004) Angew Chem, Int Ed 43:1569

    CAS  Google Scholar 

  209. Guo HM, Zucker S, Gordon MK, Toole BP, Biswas C (1997) J Biol Chem 272:24

    CAS  Google Scholar 

  210. Li XQ, Kawakami T, Aimoto S (1998) Tetrahedron Lett 39:8669

    CAS  Google Scholar 

  211. Hojo H, Haginoya E, Matsumoto Y, Nakahara Y, Nabeshima K, Toole BP, Watanabe Y (2003) Tetrahedron Lett 44:2961

    CAS  Google Scholar 

  212. Backes BJ, Virgilio AA, Ellman JA (1996) J Am Chem Soc 118:3055

    CAS  Google Scholar 

  213. Ishii A, Hojo H, Nakahara Y, Ito Y, Nakaharai Y (2002) Biosci Biotechnol Biochem 66:225

    CAS  Google Scholar 

  214. Mezzato S, Schaffrath M, Unverzagt C (2005) Angew Chem, Int Ed 44:1650

    CAS  Google Scholar 

  215. Matsushita T, Hinou H, Kurogochi M, Shimizu H, Nishimura SI (2005) Org Lett 7:877

    CAS  Google Scholar 

  216. Nakahara Y, Ogawa T (1996) Carbohydr Res 292:71

    CAS  Google Scholar 

  217. Guo ZW, Nakahara Y, Ogawa T (1997) Carbohydr Res 303:373

    CAS  Google Scholar 

  218. Guo ZW, Nakahara Y, Ogawa T (1997) Bioorg Med Chem 5:1917

    CAS  Google Scholar 

  219. Nakahara Y, Ito Y, Ogawa T (1997) Tetrahedron Lett 38:7211

    CAS  Google Scholar 

  220. Nakahara Y, Ito Y, Ogawa T (1998) Carbohydr Res 309:287

    CAS  Google Scholar 

  221. Ando S, Nakahara Y, Ito Y, Ogawa T (2000) Carbohydr Res 329:773

    CAS  Google Scholar 

  222. Hojo H, Watabe J, Nakahara Y, Ito Y, Nabeshima K, Toole BP (2001) Tetrahedron Lett 42:3001

    CAS  Google Scholar 

  223. Maemura M, Ohgaki A, Nakahara Y, Hojo H (2005) Biosci Biotechnol Biochem 69:1575

    CAS  Google Scholar 

  224. Takano Y, Habiro M, Someya M, Hojo H, Nakahara Y (2002) Tetrahedron Lett 43:8395

    CAS  Google Scholar 

  225. Guo ZW, Nakahara Y, Ogawa T (1997) Angew Chem, Int Ed Engl 36:1464

    CAS  Google Scholar 

  226. Takano Y, Kojima N, Nakahara Y, Hojo H (2003) Tetrahedron 59:8415

    CAS  Google Scholar 

  227. Kempe M, Barany G (1996) J Am Chem Soc 118:7083

    CAS  Google Scholar 

  228. Takano Y, Hojo H, Kojima N, Nakahara Y (2004) Org Lett 6:3135

    CAS  Google Scholar 

  229. Ichiyanagi T, Takatani M, Sakamoto K, Nakahara Y, Ito Y, Hojo H (2002) Tetrahedron Lett 43:3297

    CAS  Google Scholar 

  230. Takemura T, Hojo H, Nakahara Y, Ishimizu T, Hase S (2004) Org Biomol Chem 2:133

    CAS  Google Scholar 

  231. Kitamura M, Hojo H, Nakahara Y, Ishimizu T, Hase S (2004) Glycoconjugate J 21:197

    CAS  Google Scholar 

  232. Tolborg JF, Petersen L, Jensen KJ, Mayer C, Jakeman DL, Warren RAJ, Withers SG (2002) J Org Chem 67:4143

    CAS  Google Scholar 

  233. Kim YW, Lee SS, Warren RAJ, Withers SG (2004) J Biol Chem 279:42787

    CAS  Google Scholar 

  234. Schuster M, Wang P, Paulson JC, Wong CH (1994) J Am Chem Soc 116:1135

    CAS  Google Scholar 

  235. Fumoto M, Hinou H, Matsushita T, Kurogochi M, Ohta T, Ito T, Yamada K, Takimoto A, Kondo H, Inazu T, Nishimura SI (2005) Angew Chem, Int Ed 44:2534

    CAS  Google Scholar 

  236. Fumoto M, Hinou H, Ohta T, Ito T, Yamada K, Takimoto A, Kondo H, Shimizu H, Inazu T, Nakahara Y, Nishimura SI (2005) J Am Chem Soc 127:11804

    CAS  Google Scholar 

  237. Ito H, Kameyana A, Sato T, Kiyohara K, Nakahara Y, Narimatsu H (2005) Angew Chem, Int Ed 44:4547

    CAS  Google Scholar 

  238. Wang L, Schultz PG (2005) Angew Chem, Int Ed 44:34

    CAS  Google Scholar 

  239. Wang L, Schultz PG (2001) Chem Biol 8:883

    CAS  Google Scholar 

  240. Wang L, Magliery TJ, Liu DR, Schultz PG (2000) J Am Chem Soc 122:5010

    CAS  Google Scholar 

  241. Wang L, Brock A, Herberich B, Schultz PG (2001) Science 292:498

    CAS  Google Scholar 

  242. Santoro SW, Wang L, Herberich B, King DS, Schultz PG (2002) Nat Biotechnol 20:1044

    CAS  Google Scholar 

  243. Xu R, Hanson SR, Zhang ZW, Yang YY, Schultz PG, Wong CH (2004) J Am Chem Soc 126:15654

    CAS  Google Scholar 

  244. Zhang ZW, Gildersleeve J, Yang YY, Xu R, Loo JA, Uryu S, Wong CH, Schultz PG (2004) Science 303:371

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489, Berlin, Germany

    Christian Haase & Oliver Seitz

Authors
  1. Christian Haase
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Oliver Seitz
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Oliver Seitz .

Editor information

Valentin Wittmann

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Haase, C., Seitz, O. (2006). Chemical Synthesis of Glycopeptides. In: Wittmann, V. (eds) Glycopeptides and Glycoproteins. Topics in Current Chemistry, vol 267. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_043

Download citation

Publish with us

Policies and ethics

Search

Navigation