Skip to main content
SpringerLink
Log in

Glycosyltransferase-Catalyzed Synthesis of Non-Natural Oligosaccharides

  • Chapter
  • First Online:
Biocatalysis - From Discovery to Application

Part of the book series: Topics in Current Chemistry ((4143,volume 200))

Abstract

Enzymes are indispensable tools in modern organic synthesis. Recent progress in cloning techniques, microbiology and protein purification supply an ever growing number and quantity of preparatively useful biocatalysts. Initially used to synthesize compounds found in nature, enzymes are now probed on non-natural substrates to an increasing degree. They work on highly functional and unprotected substrates under mild and environmentally friendly conditions. In addition, they exhibit an excellent chemo-, regio- and stereoselectivity. The following article will focus on the application of glycosyltransferases in the area of molecular glycobiology. Selected reactions with non-natural substrates will be discussed.

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

Access this chapter

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight 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.

Similar content being viewed by others

References

  1. Kennedy JF (1988) Carbohydrate chemistry. Clarendon Press, Oxford

    Google Scholar 

  2. Aspinall GO (1982-1985) The polysaccharides, vols I–III. Academic Press, New York

    Google Scholar 

  3. Sandhoff K, Yussuf HKM (1991) TIGG 3(11):152

    CAS  Google Scholar 

  4. Fukuda M (1994) In: Fukuda M, Hindsgaul O (eds) Molecular glycobiology. IRL-Press, Oxford, p 1

    Google Scholar 

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

    Article  CAS  Google Scholar 

  6. Miller DJ, Macek MB (1992) Nature 357:589

    Article  CAS  Google Scholar 

  7. Singhal A, Hakomori S-I (1990) Bioassays 12:223

    Article  CAS  Google Scholar 

  8. Fukuda M (1992) In: Fukuda M (ed) Cell surface carbohydrates and cell development. CRC Press, Boca Raton, p 127

    Google Scholar 

  9. Carbone FR, Gleesen FA (1997) Glycobiology 7:725

    Article  CAS  Google Scholar 

  10. Sandrin MS, McKenzie IFC (1994) Immunol Rev 141:169

    Article  CAS  Google Scholar 

  11. Varki A (1993) Glycobiology 3:97

    Article  CAS  Google Scholar 

  12. Haywood AM (1994) J Virol 68:1

    CAS  Google Scholar 

  13. Karlsson K-A (1995) Carbohydr Eur 14

    Google Scholar 

  14. McCoy JJ, Mann BJ, Petri WA (1994) Infect Immunol 62:3045

    CAS  Google Scholar 

  15. Muramatsu T (1993) Glycobiology 3:291

    Article  CAS  Google Scholar 

  16. Witzcak ZI (1995) Curr Med Chem 1:392

    Google Scholar 

  17. McAuliffe JC, Hindsgaul O (1997) Chem Ind 3:170

    Google Scholar 

  18. Lowe JB (1994) In: Fukuda M, Hindsgaul O (eds) Molecular glycobiology. IRL-Press, Oxford, p 163

    Google Scholar 

  19. Giannis A (1994) Angew Chem Int Ed Engl 33:178

    Article  Google Scholar 

  20. Weinhold EG, Knowles JR (1992) J Am Chem Soc 114:9270

    Article  CAS  Google Scholar 

  21. Roy R, Andersson FO, Harms G, Kelm S, Schazer R (1992) Angew Chem Int Ed Engl 31:1478

    Article  Google Scholar 

  22. Parker W, Lateef J, Everet ML, Platt JL (1996) Glycobiology 6:499

    Article  CAS  Google Scholar 

  23. Neethling FA, Joziasse D, Bovin N, Cooper DKC, Oriol R (1996) Transplant Int 9:98

    Article  CAS  Google Scholar 

  24. Kanie O, Hindsgaul O (1992) Curr Opin Struct Biol 2:674

    Article  CAS  Google Scholar 

  25. a Khan SH, Hindsgaul O (1994) In: Fukuda M, Hindsgaul O (eds) Molecular glycobiology. IRL-Press, Oxford, p 206

    Google Scholar 

  26. b Schachter H (1994) In: Fukuda M, Hindsgaul O (eds) Molecular glycobiology. IRLPress, Oxford, p 88

    Google Scholar 

  27. Wong C-H, Haynie SL, Whitesides GM (1982) J Org Chem 47:5416

    Article  CAS  Google Scholar 

  28. Augé C, Mathieu C, Mérienne C (1986) Carbohydr Res 151:147

    Article  Google Scholar 

  29. Ichikawa J (1997) In: Large DG, Warren CD (eds) Glycopeptides and related Ccompounds. Marcel Dekker, New York, p 79

    Google Scholar 

  30. Fukuda M, Hindsgaul O (1994) Molecular glycobiology. IRL-Press, Oxford

    Google Scholar 

  31. Wong C-H, Whitesides GM (1994) Enzymes in synthetic organic chemistry. Tetrahedron Organic Chem Series, vol 12. Pergamon Press, Oxford

    Google Scholar 

  32. Large DG, Warren CD (1997) Glycopeptides and related compounds. Marcel Dekker, New York

    Google Scholar 

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

    Article  CAS  Google Scholar 

  34. Leloir LF (1971) Science 172:1299

    Article  CAS  Google Scholar 

  35. Unverzagt C, Kunz H, Paulson JC (1990) J Am Chem Soc 112:5893

    Article  Google Scholar 

  36. Ichikawa Y, Liu JL-C, Shen G-J, Wong C-H (1991) J Am Chem Soc 113:6300

    Article  CAS  Google Scholar 

  37. Heidlas JE, Williams KW, Whitesides GM (1992) Acc Chem Res 25:307

    Article  CAS  Google Scholar 

  38. YAMASA-Corporation 1-23-8, Nihonbashi-Kakigaracho, Chou-ku, Tokyo 103, Japan

    Google Scholar 

  39. Chappell MD, Halcomb RL (1997) Tetrahedron 53:11,109

    Article  CAS  Google Scholar 

  40. Kajihara Y, Ebata T, Koseki K, Kodama H, Matsushita H, Hashimoto H (1995) J Org Chem 60:5732

    Article  CAS  Google Scholar 

  41. Kittelmann M, Klein T, Kragl U, Wandrey C, Ghisalba O (1995) Appl Microbiol Biotechnol 44:59

    CAS  Google Scholar 

  42. Adelhorst K, Whitesides GM (1993) Carbohydr Res 242:69

    Article  CAS  Google Scholar 

  43. Wittmann V, Wong C-H (1997) J Org Chem 62:2144

    Article  CAS  Google Scholar 

  44. Baisch G, Öhrlein R (1997) Bioorg Med Chem 5:383

    Article  CAS  Google Scholar 

  45. Pallanca JE, Turner NJ (1993) J Chem Soc Perkin TransI 3017

    Google Scholar 

  46. DeLuca C, Lansing M, Creszenzi F, Martini I, Shen G-J, O’Regan M, Wong C-H (1996) Bioorg Med Chem 4:131

    Article  CAS  Google Scholar 

  47. Ko JH, Shin H-S, Kim YS, Lee DS, Kim C-H (1996) Appl Biochem Biotechnol 60:41

    CAS  Google Scholar 

  48. Yamazaki T, Warren CD, Herscovic A, Jeanloz RW (1981) Can J Chem 59:2247

    Article  CAS  Google Scholar 

  49. Gambert U, Thiem J (1997) Top Curr Chem 186:21

    CAS  Google Scholar 

  50. Palcic MM, Hindsgaul O (1996) TIGG 8:37

    CAS  Google Scholar 

  51. Guilbert B, Davis NJ, Pearce M, Aplin RT, Flitsch SL (1994) Tetrahedron Asymmetry 5:2163

    Article  CAS  Google Scholar 

  52. Baisch G, Öhrlein R (1996) Angew Chem Int Ed Engl 35:1812

    Article  CAS  Google Scholar 

  53. Öhrlein R, Ernst B, Berger EG (1992) Carbohydr Res 236:335

    Article  Google Scholar 

  54. Baisch G, Öhrlein R, Ernst B (1996) Bioorg Med Chem Lett 6:749

    Article  CAS  Google Scholar 

  55. Hayashi M, Tanaka M, Miyauchi H (1996) J Org Chem 61:2938

    Article  CAS  Google Scholar 

  56. Guilbert B, Khan TH, Flitsch SL (1992) J Chem Soc Chem Commun 1526

    Google Scholar 

  57. Goodridge GM, Guilbert B, Flitsch S, Revers L, Webberley MC, Wilson IB (1994) Bioorg Med Chem 2:1243

    Article  Google Scholar 

  58. Öhrlein R (1997) Biotrans ‘97, Abstract C10, La Grande Motte, France

    Google Scholar 

  59. Kren V, Augé C, Sedmera P, Havlícek V (1994) J Chem Soc Perkin I 2481

    Google Scholar 

  60. Schultz M, Kunz H (1993) Tetrahedron Asymmetry 4:1205

    Article  CAS  Google Scholar 

  61. Wong C-H, Schuster M, Wang P, Sears P (1993) J Am Chem Soc 115:5893

    Article  CAS  Google Scholar 

  62. Danieli B, Luisetti M, Schubert-Zsilavecz M, Likussar W, Steurer S, Riva S, Monti D, Reiner J (1997) Helv Chim Acta 80:1153

    Article  CAS  Google Scholar 

  63. Baisch G, Öhrlein R (1998) Bioorg Med Chem (in print)

    Google Scholar 

  64. Kajihara Y, Endo T, Ogasawara H, Kodama H, Hashimoto H (1995) Carbohydr Res 269:273

    Article  CAS  Google Scholar 

  65. Do K-Y, Cummings RD (1995) J Biol Chem 270:18,447

    Article  CAS  Google Scholar 

  66. Tsuruta O, Shinohara G, Yuasa H, Hashimoto H (1997) Bioorg Med Chem Lett 7:2523

    Article  CAS  Google Scholar 

  67. Gautheron-LeNarvor C, Wong C-H (1991) J Chem Soc Chem Commun 1130

    Google Scholar 

  68. Panza L, Chiappini Pl, Russo G, Monti D, Riva S (1997) J Chem Soc Perkin I 1255

    Google Scholar 

  69. Palcic MM (1994) Methods Enzymol 230:300

    CAS  Google Scholar 

  70. Yu L, Cabrera R, Ramirez J, Malinoskii VA, Brew K, Wang PG (1995) Tetrahedron Lett 36:2897

    Article  CAS  Google Scholar 

  71. Sasaki J, Mizoue K, Morimoto S, Omura S (1996) J Antibiotics 49:1110

    CAS  Google Scholar 

  72. Wiemann T, Taubken N, Zehave U, Thiem J (1994) Carbohydr Res 257:C1–C6

    Article  CAS  Google Scholar 

  73. Köpper S (1994) Carbohydr Res 265:161

    Article  Google Scholar 

  74. Schuster M, Wang P, Paulson JC, Wong C-H (1994) J Am Chem Soc 116:1135

    Article  CAS  Google Scholar 

  75. Granovsky M, Bielfeldt T, Peters S, Paulsen H, Meldal M, Brockhausen J, Brockhausen I (1994) Eur J Biochem 221:1039

    Article  CAS  Google Scholar 

  76. Miyazaki H, Fukumoto S, Okada M, Hasegawa T, Furukawa K (1997) J Biol Chem 272:24, 794

    Article  CAS  Google Scholar 

  77. Kolbinger F, Streiff M, Katopodis A (1998) J Biol Chem 273:433

    Article  CAS  Google Scholar 

  78. Baisch G, Öhrlein R, Streiff M, Kolbinger F (1998) Bioorg Med Chem Lett 8:751

    Article  CAS  Google Scholar 

  79. Lowary TL, Hindsgaul O (1993) Carbohydr Res 249:163

    Article  CAS  Google Scholar 

  80. Helland A-C, Hindsgaul O, Palcic MM, Stults CLM, Macher BA (1995) Carbohydr Res 276:91

    Article  CAS  Google Scholar 

  81. Gustaffson K, Strahan K, Preece A (1994) Immunol Rev 141:59

    Article  Google Scholar 

  82. Joziasse DH, Shaper NL, Salyer L, Van den Eijnden DH, Van der Poel AC (1990) Eur J Biochem 191:75

    Article  CAS  Google Scholar 

  83. Baisch G, Öhrlein R, Kolbinger F, Streiff M (1998) Biorg Med Chem Lett 8:1575

    Article  CAS  Google Scholar 

  84. Kochetkov NK, Shibaev VN (1974) Izv Akad Nauk SSSR Ser Khim 5:1169

    Google Scholar 

  85. Staudacher E (1996) TIGG 8:391

    CAS  Google Scholar 

  86. Koszdin KL, Bowen BR (1992) Biochem Biophys Res Commun 187:152

    Article  CAS  Google Scholar 

  87. Ge Z, Chan NWC, Palcic MM, Taylor DE (1997) J Biol Chem 272:21,357

    Article  CAS  Google Scholar 

  88. Kashem MA, Wlasichuk KB, Gregson JM, Venot AP (1993) Carbohydr Res 250:129

    Article  CAS  Google Scholar 

  89. Ball GE, O’Neill RA, Shultz JE, Lowe JB, Weston BW, Nagy JO, Brown EG, Hobbs CJ, Bednarsky MD (1992) J Am Chem Soc 114:5449

    Article  CAS  Google Scholar 

  90. Baisch G, Öhrlein R, Katopodis A, Ernst B (1996) Bioorg Med Chem Lett 6:759

    Article  CAS  Google Scholar 

  91. Baisch G, Öhrlein R, Streiff M, Katopodis A, Kolbinger F (1997) Bioorg Med Chem Lett 7:2447

    Article  CAS  Google Scholar 

  92. Hällgren C, Hindsgaul O (1995) J Carbohydr Chem 14:453

    Article  Google Scholar 

  93. Baisch G, Öhrlein R, Katopodis A, (1997) Bioorg Med Chem Lett 7:2431

    Article  CAS  Google Scholar 

  94. Du M, Hindsgaul O (1996) Carbohydr Res 286:87

    Article  CAS  Google Scholar 

  95. Sasaki K, Kurata K, Funayama K, Nagata M, Watanabe E, Ohta S, Hanai N, Nishi T (1994) J Biol Chem 269:13,730

    Google Scholar 

  96. Baisch G, Öhrlein R, Streiff M, Kolbinger F (1998) Bioorg Med Chem Lett 8:161

    Article  CAS  Google Scholar 

  97. Baisch G, Öhrlein R (1998) Carbohydr Res in print

    Google Scholar 

  98. Baisch G, Öhrlein R, Streiff M, Kolbinger F (1998) Bioorg Med Chem Lett 8:755

    Article  CAS  Google Scholar 

  99. Murray BW, Wittmann V, Burkhart MD, Hung S-C, Wong C-H (1997) Biochemistry 36:823

    Article  CAS  Google Scholar 

  100. Baisch G, Öhrlein R, Katopodis A (1996) Bioorg Med Chem Lett 6:2953

    Article  CAS  Google Scholar 

  101. Sasaki K (1996) TIGG 8:195

    CAS  Google Scholar 

  102. Brossmer R, Gross HJ (1994) Methods Enzymol 247:153

    Article  CAS  Google Scholar 

  103. Chappell MD, Halcomb RL (1997) Tetrahedron 53:11, 109

    Article  CAS  Google Scholar 

  104. Wen DX, Livingston BD, Medziharadszky MF, Kelm S, Burlingame AL, Paulson JC (1992) J Biol Chem 267:21, 011

    CAS  Google Scholar 

  105. Baisch G, Öhrlein R, Streiff M, Ernst B (1996) Bioorg Med Chem Lett 6:755

    Article  CAS  Google Scholar 

  106. Baisch G, Öhrlein R, Streiff M (1998) Bioorg Med Chem Lett 8:157

    Article  CAS  Google Scholar 

  107. Öhrlein R, Hindsgaul O, Palcic MM (1993) Carbohydr Res 244:149

    Article  Google Scholar 

  108. Gross HJ, Brossmer R (1995) Glycoconjugate J 12:739

    Article  CAS  Google Scholar 

  109. Van Dorst JALM, Tikkanen JM, Krezdorn CH, Streiff M, Berger EG, van Kuik JA, Kamerling JP, Viegenthart JFG (1996) Eur J Biochem 242:674

    Article  Google Scholar 

  110. Crawley SC, Palcic MM (1996) Modern Methods Carbohydr Synth 492

    Google Scholar 

  111. Paulsen H, Meinjohanns E, Reck F, Brockhausen I (1993) Liebigs Ann 737

    Google Scholar 

  112. Reck F, Meinjohanns E, Tan J, Grey AA, Paulsen H, Schachter H (1995) Carbohydr Res 275:221

    Article  CAS  Google Scholar 

  113. Alton G, Srivastava G, Kaur KJ, Hindsgaul O (1994) Bioorg Med Chem 2:675

    Article  CAS  Google Scholar 

  114. Ogawa S, Furuya T, Tsunoda H, Hindsgaul O, Stangier K, Palcic MM (1995) Carbohydr Res 271:197

    Article  CAS  Google Scholar 

  115. Watt GM, Revers L, Webberley MC, Wilson IBH, Flitsch S (1997) Angew Chem Int Ed Engl 36:2354

    Article  CAS  Google Scholar 

  116. Herrmann GF, Wang P, Shen G-J, Garcia-Junceda E, Khan S, Matta KL, Wong C-H (1994) J Am Chem Soc 59:6356

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. S-507.702, NOVARTIS Pharma AG, CH-4002, Basle, Switzerland

    Reinhold Öhrlein

Authors
  1. Reinhold Öhrlein
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut für Organische Chemie, Technische Universität Darmstadt, Petersenstratße 22, D-64287, Darmstadt, Germany

    Wolf-Dieter Fessner

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Öhrlein, R. (1999). Glycosyltransferase-Catalyzed Synthesis of Non-Natural Oligosaccharides. In: Fessner, WD., et al. Biocatalysis - From Discovery to Application. Topics in Current Chemistry, vol 200. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-68116-7_8

Download citation

  • DOI: https://doi.org/10.1007/3-540-68116-7_8

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-64942-7

  • Online ISBN: 978-3-540-68116-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation