Skip to main content
SpringerLink
Log in

Enzymatic Synthesis of Glycopeptides and Glycoproteins

  • Chapter
  • First Online:
Glycopeptides and Glycoproteins

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

Abstract

Glycosylation is recognized as important in biology, though the discovery of previously unknown functions associated with carbohydrates is ongoing. As the most complex and diverse post-translational modification, determining the structure-function relationships for glycosylation remains difficult due to the heterogeneous expression of glycoproteins as mixtures of glycoforms. Thus the synthesis of glycoproteins and glycopeptides with defined glycan structures is essential for detailed determination of the role of glycosylation. This review describes the use of enzymes for the synthesis of glycopeptides and glycoproteins, including their use as catalysts for glycosidic linkage formation and elaboration, peptide bond formation, and modification.

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.

References

  1. Dwek RA (1996) Chem Rev 96:683

    CAS  Google Scholar 

  2. Sears P, Wong CH (1998) Cell Mol Life Sci 54:223

    CAS  Google Scholar 

  3. Lis H, Sharon N (1993) Eur J Biochem 218:1

    CAS  Google Scholar 

  4. Varki A (1993) Glycobiol 3:97

    CAS  Google Scholar 

  5. Durand G, Seta N (2000) Clin Chem 46:795

    CAS  Google Scholar 

  6. Dube DH, Bertozzi CR (2005) Nat Rev Drug Discov 4:477

    CAS  Google Scholar 

  7. Rudd PM, Dwek RA (1997) Crit Rev Biochem Mol Biol 32:1

    CAS  Google Scholar 

  8. Prescher JA, Bertozzi CR (2005) Nat Chem Biol 1:13

    CAS  Google Scholar 

  9. Wong CH, Haynie SL, Whitesides GM (1982) J Org Chem 47:5416

    CAS  Google Scholar 

  10. Herrmann GF, Ichikawa Y, Wandrey C, Gaeta FCA, Paulson JC, Wong CH (1993) Tetrahedron Lett 34:3091

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  12. Sallas F, Nishimura SI (2000) J Chem Soc Perkin Trans 1:2091

    Google Scholar 

  13. Matsuda M, Nishimura SI, Nakajima F, Nishimura T (2001) J Med Chem 44:715

    CAS  Google Scholar 

  14. Leppänen A, Mehta P, Ouyang YB, Ju TZ, Helin J, Moore KL, van Die I, Canfield WM, McEver RP, Cummings RD (1999) J Biol Chem 274:24838

    Google Scholar 

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

    Google Scholar 

  16. Leppänen A, White SP, Helin J, McEver RP, Cummings RD (2000) Glycobiol 10:1106

    Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  19. Izumi M, Shen GJ, Wacowich-Sgarbi S, Nakatani T, Plettenburg O, Wong CH (2001) J Am Chem Soc 123:10909

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  21. Zeng XX, Nakaaki Y, Murata T, Usui T (2000) Arch Biochem Biophys 383:28

    CAS  Google Scholar 

  22. Gambert U, Thiem J (1999) Eur J Org Chem 1999:107

    Google Scholar 

  23. George SK, Holm B, Reis CA, Schwientek T, Clausen H, Kihlberg J (2001) J Chem Soc Perkin Trans 1:880

    Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  26. Unverzagt C, Kunz H, Paulson JC (1990) J Am Chem Soc 112:9308

    CAS  Google Scholar 

  27. Unverzagt C, Kelm S, Paulson JC (1994) Carbohydr Res 251:285

    CAS  Google Scholar 

  28. Unverzagt C (1996) Angew Chem Int Ed Engl 35:2350

    CAS  Google Scholar 

  29. Unverzagt C (1997) Carbohydr Res 305:423

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  31. Wong CH, Schuster M, Wang P, Sears P (1993) J Am Chem Soc 115:5893

    CAS  Google Scholar 

  32. Tai VWF, Imperiali B (2001) J Org Chem 66:6217

    CAS  Google Scholar 

  33. Walsh CT, Losey HC, Meyers CLF (2003) Biochem Soc Trans 31:487

    CAS  Google Scholar 

  34. Walsh C, Meyers CLF, Losey HC (2003) J Med Chem 46:3425

    CAS  Google Scholar 

  35. Solenberg PJ, Matsushima P, Stack DR, Wilkie SC, Thompson RC, Baltz RH (1997) Chem Biol 4:195

    CAS  Google Scholar 

  36. Losey HC, Jiang JQ, Biggins JB, Oberthur M, Ye XY, Dong SD, Kahne D, Thorson JS, Walsh CT (2002) Chem Biol 9:1305

    CAS  Google Scholar 

  37. Fu X, Albermann C, Jiang JQ, Liao JC, Zhang CS, Thorson JS (2003) Nat Biotechnol 21:1467

    CAS  Google Scholar 

  38. Losey HC, Peczuh MW, Chen Z, Eggert US, Dong SD, Pelczer I, Kahne D, Walsh CT (2001) Biochemistry (Moscow) 40:4745

    CAS  Google Scholar 

  39. Watt GM, Lowden PAS, Flitsch SL (1997) Curr Opin Struct Biol 7:652

    CAS  Google Scholar 

  40. Crout DHG, Vic G (1998) Curr Opin Chem Biol 2:98

    CAS  Google Scholar 

  41. Palcic MM (1999) Curr Opin Biotechnol 10:616

    CAS  Google Scholar 

  42. Koeller KM, Wong CH (2000) Chem Rev 100:4465

    CAS  Google Scholar 

  43. Ajisaka K, Miyasato M (2000) Biosci Biotechnol Biochem 64:1743

    CAS  Google Scholar 

  44. Suzuki K, Fujimoto H, Ito Y, Sasaki T, Ajisaka K (1997) Tetrahedron Lett 38:1211

    CAS  Google Scholar 

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

    Google Scholar 

  46. Hokke CH, van den Eijnden DH (1997) Carbohydr Res 305:463

    CAS  Google Scholar 

  47. Jahn M, Withers SG (2003) Biocatal Biotransform 21:159

    CAS  Google Scholar 

  48. Perugino G, Trincone A, Rossi M, Moracci M (2004) Trends Biotechnol 22:31

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  51. Fujita K, Tanaka N, Sano M, Kato I, Asada Y, Takegawa K (2000) Biochem Biophys Res Commun 267:134

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  54. Wang LX, Song H, Liu S, Lu H, Jiang S, Ni J, Li H (2005) Chem Bio Chem 6:1068

    CAS  Google Scholar 

  55. Li B, Zeng Y, Hauser S, Song H, Wang LX (2005) J Am Chem Soc 127:9692

    CAS  Google Scholar 

  56. Yamamoto K (2001) J Biosci Bioeng 92:493

    CAS  Google Scholar 

  57. Haneda K, Inazu T, Yamamoto K, Kumagai H, Nakahara Y, Kobata A (1996) Carbohydr Res 292:61

    CAS  Google Scholar 

  58. Yamamoto K, Fujimori K, Haneda K, Mizuno M, Inazu T, Kumagai H (1997) Carbohydr Res 305:415

    CAS  Google Scholar 

  59. Haneda K, Inazu T, Mizuno M, Iguchi R, Yamamoto K, Kumagai H, Aimoto S, Suzuki H, Noda T (1998) Bioorg Med Chem Lett 8:1303

    CAS  Google Scholar 

  60. Mizuno M, Haneda K, Iguchi R, Muramoto I, Kawakami T, Aimoto S, Yamamoto K, Inazu T (1999) J Am Chem Soc 121:284

    CAS  Google Scholar 

  61. Haneda K, Inazu T, Mizuno M, Iguchi R, Tanabe H, Fujimori K, Yamamoto K, Kumagai H, Tsumori K, Munekata E (2001) Biochim Biophys Acta 1526:242

    CAS  Google Scholar 

  62. Saskiawan I, Mizuno M, Inazu T, Haneda K, Harashima S, Kumagai H, Yamamoto K (2002) Arch Biochem Biophys 406:127

    CAS  Google Scholar 

  63. Akaike E, Tsutsumida M, Osumi K, Fujita M, Yamanoi T, Yamamoto K, Fujita K (2004) Carbohydr Res 339:719

    CAS  Google Scholar 

  64. Kato T, Fujita K, Takeuchi M, Kobayashi K, Natsuka S, Ikura K, Kumagai H, Yamamoto Y (2002) Glycobiology 12:581

    CAS  Google Scholar 

  65. Muramatsu T (2000) Glycoconj J 17:577

    CAS  Google Scholar 

  66. Yamamoto S, Muramatsu H, Muramatsu T (2005) Glycoconj J 22:35

    CAS  Google Scholar 

  67. Trimble RB, Atkinson PH, Tarentino AL, Plummer TH, Maley F, Tomer KB (1986) J Biol Chem 261:2000

    Google Scholar 

  68. Bardales RM, Bhavanandan VP (1989) J Biol Chem 264:19893

    CAS  Google Scholar 

  69. Ashida H, Yamamoto K, Murata T, Usui T, Kumagai H (2000) Arch Biochem Biophys 373:394

    CAS  Google Scholar 

  70. Ishiikarakasa I, Iwase H, Hotta K, Tanaka Y, Omura S (1992) Biochem J 288:475

    CAS  Google Scholar 

  71. Ajisaka K, Miyasato M, Ishii-Karakasa I (2001) Biosci Biotechnol Biochem 65:1240

    CAS  Google Scholar 

  72. Ishido K, Takagaki K, Iwafune M, Yoshihara S, Sasaki M, Endo M (2002) J Biol Chem 277:11889

    CAS  Google Scholar 

  73. Witte K, Sears P, Martin R, Wong CH (1997) J Am Chem Soc 119:2114

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  75. Malet C, Planas A (1998) FEBS Lett 440:208

    CAS  Google Scholar 

  76. Faijes M, Fairweather JK, Driguez H, Planas A (2001) Chem Eur J 7:4651

    CAS  Google Scholar 

  77. Faijes M, Perez X, Perez O, Planas A (2003) Biochemistry (Moscow) 42:13304

    CAS  Google Scholar 

  78. Faijes M, Ima T, Bulone V, Planas A (2004) Biochem J 380:635

    CAS  Google Scholar 

  79. van Lieshout J, Faijes M, Nieto J, van der Oost J, Planas A (2004) Archaea 1:285

    Google Scholar 

  80. Bordusa F (2002) Chem Rev 102:4817

    CAS  Google Scholar 

  81. Jackson DY, Burnier J, Quan C, Stanley M, Tom J, Wells JA (1994) Science 266:243

    CAS  Google Scholar 

  82. Sears P, Schuster M, Wang P, Witte K, Wong CH (1994) J Am Chem Soc 116:6521

    CAS  Google Scholar 

  83. Moree WJ, Sears P, Kawashiro K, Witte K, Wong CH (1997) J Am Chem Soc 119:3942

    CAS  Google Scholar 

  84. Nakatsuka T, Sasaki T, Kaiser ET (1987) J Am Chem Soc 109:3808

    CAS  Google Scholar 

  85. Abrahmsen L, Tom J, Burnier J, Butcher KA, Kossiakoff A, Wells JA (1991) Biochemistry (Moscow) 30:4151

    CAS  Google Scholar 

  86. Zhong ZY, Wong CH (1991) Biomed Biochim Acta 50:S9

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  88. Tolbert TJ, Wong CH (2004) Methods Mol Biol 283:267

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  90. Dawson PE, Kent SBH (2000) Ann Rev Biochem 69:923

    CAS  Google Scholar 

  91. Erlanson DA, Chytil M, Verdine GL (1996) Chem Biol 3:981

    CAS  Google Scholar 

  92. Muir TW (2001) Synlett:733

    Google Scholar 

  93. Harris JL, Backes BJ, Leonetti F, Mahrus S, Ellman JA, Craik CS (2000) Proc Natl Acad Sci USA 97:7754

    CAS  Google Scholar 

  94. Matthews DJ, Wells JA (1993) Science 260:1113

    CAS  Google Scholar 

  95. Tolbert TJ, Wong CH (2002) Angew Chem Int Ed 41:2171

    CAS  Google Scholar 

  96. Tolbert TJ, Wong CH (2004) Methods Mol Biol 283:255

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  98. Kadereit D, Waldmann H (2001) Chem Rev 101:3367

    CAS  Google Scholar 

  99. Ishii H, Funabashi K, Mimura Y, Inoue Y (1990) Bull Chem Soc Jpn 63:3042

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  101. Cantacuzene D, Attal S, Bay S (1991) Biomed Biochim Acta 50:S231

    CAS  Google Scholar 

  102. Eberling J, Braun P, Kowalczyk D, Schultz M, Kunz H (1996) J Org Chem 61:2638

    CAS  Google Scholar 

  103. Tokuda Y, Takahashi Y, Matoishi K, Ito Y, Sugai T (2002) Synlett:57

    Google Scholar 

  104. Hermann P (1991) Biomed Biochim Acta 50:S19

    CAS  Google Scholar 

  105. Schultz M, Hermann P, Kunz H (1992) Synlett:37

    Google Scholar 

  106. Reissmann S, Greiner G (1992) Int J Pept Protein Res 40:110

    CAS  Google Scholar 

  107. Attal S, Bay S, Cantacuzene D (1992) Tetrahedron 48:9251

    CAS  Google Scholar 

  108. Reetz MT (2002) Curr Opin Chem Biol 6:145

    CAS  Google Scholar 

  109. Koeller KM, Wong CH (2001) Nature 409:232

    CAS  Google Scholar 

  110. Pathak T, Waldmann H (1998) Curr Opin Chem Biol 2:112

    CAS  Google Scholar 

  111. Margolin AL, Klibanov AM (1987) J Am Chem Soc 109:3802

    CAS  Google Scholar 

  112. Gewehr M, Kunz H (1997) Synthesis:1499

    Google Scholar 

  113. Eisele F, Owen DJ, Waldmann H (1999) Bioorg Med Chem 7:193

    CAS  Google Scholar 

  114. Waldmann H, Braun P, Kunz H (1991) Biomed Biochim Acta 50:S243

    CAS  Google Scholar 

  115. Braun P, Waldmann H, Kunz H (1992) Synlett:39

    Google Scholar 

  116. Braun P, Waldmann H, Kunz H (1993) Bioorg Med Chem 1:197

    CAS  Google Scholar 

  117. Braun P, Davies GM, Price MR, Williams PM, Tendler SJB, Kunz H (1998) Bioorg Med Chem 6:1531

    CAS  Google Scholar 

  118. Kunz H, Kowalczyk D, Braun P, Braum G (1994) Angew Chem Int Ed Engl 33:336

    Google Scholar 

  119. Sander J, Waldmann H (1999) Angew Chem Int Ed 38:1250

    CAS  Google Scholar 

  120. Sander J, Waldmann H (2000) Chem Eur J 6:1564

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  122. Bowman KG, Bertozzi CR (1999) Chem Biol 6:R9

    CAS  Google Scholar 

  123. Chapman E, Best MD, Hanson SR, Wong CH (2004) Angew Chem Int Ed 43:3526

    CAS  Google Scholar 

  124. Burkart MD, Izumi M, Wong CH (1999) Angew Chem Int Ed 38:2747

    CAS  Google Scholar 

  125. Burkart MD, Wong CH (1999) Anal Biochem 274:131

    CAS  Google Scholar 

  126. Burkart MD, Izumi M, Chapman E, Lin CH, Wong CH (2000) J Org Chem 65:5565

    CAS  Google Scholar 

  127. Kruger RG, Lu W, Oberthur M, Tao JH, Kahne D, Walsh CT (2005) Chem Biol 12:131

    CAS  Google Scholar 

  128. Ramos D, Rollin P, Klaffke W (2000) Angew Chem Int Ed 39:396

    CAS  Google Scholar 

  129. Ramos D, Rollin P, Klaffke W (2001) J Org Chem 66:2948

    CAS  Google Scholar 

  130. Ohta T, Miura N, Fujitani N, Nakajima F, Niikura K, Sadamoto R, Guo CT, Suzuki T, Suzuki Y, Monde K, Nishimura SI (2003) Angew Chem Int Ed 42:5186

    CAS  Google Scholar 

  131. Sato M, Sadamoto R, Niikura K, Monde K, Kondo H, Nishimura SI (2004) Angew Chem Int Ed 43:1516

    CAS  Google Scholar 

  132. Sato M, Furuike T, Sadamoto R, Fujitani N, Nakahara T, Niikura K, Monde K, Kondo H, Nishimura SI (2004) J Am Chem Soc 126:14013

    CAS  Google Scholar 

  133. Lin H, Thayer DA, Wong CH, Walsh CT (2004) Chem Biol 11:1635

    CAS  Google Scholar 

  134. Lin H, Walsh CT (2004) J Am Chem Soc 126:13998

    CAS  Google Scholar 

  135. Wang L, Schultz PG (2004) Angew Chem Int Ed Engl 44:34

    Google Scholar 

  136. Liu H, Wang L, Brock A, Wong CH, Schultz PG (2003) J Am Chem Soc 125:1702

    CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  139. Wildt S, Gerngross TU (2005) Nat Rev Microbiol 3:119

    CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the National Institutes for Health for research support. D.A.T. is supported by the Norton B. Gilula Graduate Student fellowship.

Author information

Authors and Affiliations

  1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd., 92037, La Jolla, California, USA

    Desiree A. Thayer & Chi-Huey Wong

Authors
  1. Desiree A. Thayer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chi-Huey Wong
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chi-Huey Wong .

Editor information

Valentin Wittmann

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Thayer, D.A., Wong, CH. (2006). Enzymatic Synthesis of Glycopeptides and Glycoproteins. In: Wittmann, V. (eds) Glycopeptides and Glycoproteins. Topics in Current Chemistry, vol 267. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_032

Download citation

Publish with us

Policies and ethics

Search

Navigation