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Trypanosomal Trans-sialidases: Valuable Synthetic Tools and Targets for Medicinal Chemistry

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SialoGlyco Chemistry and Biology II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 367))

Abstract

In contrast to the general hydrolases, trans-sialidase from Trypanosoma cruzi (TcTS) shows excellent regio- and stereoselectivity as well as high yields in transfer reactions. Discussed are the occurrence of trans-sialidases and studies on the transfer mechanism. In detail, the preparative use by chemoenzymatic syntheses with TcTS are outlined with emphasis on the design of modified donor and acceptor substrates. Another section focuses on attempts to develop inhibitors for TcTS, and these endeavors are based on donor- and acceptor-inspired modifications as well as on some completely different structures.

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References

  1. Morel CM, Lazdins J (2003) Nat Rev Microbiol 1:14

    Article  Google Scholar 

  2. Chagas C (1909) Mem Inst Oswaldo Cruz 1:159

    Article  Google Scholar 

  3. Marshall E (1995) Science 267:811

    Article  CAS  Google Scholar 

  4. Teixeira ARL, Nitz N, Guimaro MC, Gomes C, Santos-Buch CA (2006) Postgrad Med J 82:788

    Article  CAS  Google Scholar 

  5. Schauer R, Reuter G, Muehlpfordt H, Andrade AFB, Pereira MEA (1983) Hoppe-Seyler's Z Physiol Chem 364:1053

    Article  CAS  Google Scholar 

  6. Barrett MP, Burchmore RJS, Stich A, Lazzari JO, Frasch AC, Cazzulo JJ, Krishna S (2003) Lancet 362:1469

    Article  Google Scholar 

  7. Alves MJM, Colli W (2007) IUBMB Life 59:274

    Article  CAS  Google Scholar 

  8. Schenkman S, Jiang MS, Hart GW, Nussenzweig V (1991) Cell 65:1117

    Article  CAS  Google Scholar 

  9. Rubin-de-Celis SSC, Uemura H, Yoshida N, Schenkman S (2006) Cell Microbiol 8:1888

    Article  Google Scholar 

  10. Leguizamon MS, Mocetti E, Rivello HG, Argibay P, Campetella O (1999) J Infect Dis 180:1398

    Article  CAS  Google Scholar 

  11. Erdmann H, Steeg C, Koch-Nolte F, Fleischer B, Jacobs T (2009) Cell Microbiol 11:1600

    Article  CAS  Google Scholar 

  12. Pereira ME, Zhang K, Gong Y, Herrera EM, Ming M (1996) Infect Immun 64:3884

    CAS  Google Scholar 

  13. Amaya MF, Buschiazzo A, Nguyen T, Alzari PM (2003) J Mol Biol 325:773

    Article  CAS  Google Scholar 

  14. Buschiazzo A, Campetella O, Frasch ACC (1997) Glycobiology 7:1167

    Article  CAS  Google Scholar 

  15. Montagna G, Cremona ML, Paris G, Amaya MF, Buschiazzo A, Alzari PM, Frasch ACC (2002) Eur J Biochem 269:2941

    Article  CAS  Google Scholar 

  16. Koliwer-Brandl H, Gbem TT, Waespy M, Reichert O, Mandel P, Drebitz E, Dietz F, Kelm S (2011) BMC Biochem 12:39

    Google Scholar 

  17. Engstler M, Reuter G, Schauer R (1993) Mol Biochem Parasitol 61:1

    Article  CAS  Google Scholar 

  18. Nagamune K, Acosta-Serrano A, Uemura H, Brun R, Kunz-Renggli C, Maeda Y, Ferguson MAJ, Kinoshita T (2004) J Exp Med 199:1445

    Article  CAS  Google Scholar 

  19. Aguero F, Campo V, Cremona L, Jager A, Di Noia JM, Overath P, Sanchez DO, Frasch AC (2002) Infect Immun 70:7140

    Article  CAS  Google Scholar 

  20. Pereira ME (1983) Science 219:1444

    Article  CAS  Google Scholar 

  21. Previato JO, Andrade AFB, Pessolani MCV, Mendonca-Previato L (1985) Mol Biochem Parasitol 16:85

    Article  CAS  Google Scholar 

  22. Uemura H, Schenkman S, Nussenzweig V, Eichinger D (1992) EMBO J 11:3837

    CAS  Google Scholar 

  23. Scudder P, Doom JP, Chuenkova M, Manger ID, Pereira MEA (1993) J Biol Chem 268:9886

    CAS  Google Scholar 

  24. Schenkman S, Chaves LB, Pontes de Carvalho LC, Eichinger D (1994) J Biol Chem 269:7970

    Google Scholar 

  25. Buschiazzo A, Amaya MF, Cremona ML, Frasch AC, Alzari PM (2002) Mol Cell 10:757

    Article  CAS  Google Scholar 

  26. Amaya MF, Watts AG, Damager I, Wehenkel A, Nguyen T, Buschiazzo A, Paris G, Frasch AC, Withers SG, Alzari PM (2004) Structure 12:775

    Article  CAS  Google Scholar 

  27. Cremona ML, Sanchez DO, Frasch ACC, Campetella O (1995) Gene 160:123

    Article  CAS  Google Scholar 

  28. Watts AG, Damager I, Amaya ML, Buschiazzo A, Alzari P, Frasch AC, Withers SG (2003) J Am Chem Soc 125:7532

    Article  CAS  Google Scholar 

  29. Damager I, Buchini S, Amaya MF, Buschiazzo A, Alzari P, Frasch AC, Watts A, Withers SG (2008) Biochemistry 47:3507

    Article  CAS  Google Scholar 

  30. Todeschini AR, Mendonça-Previato L, Previato JO, Varki A, van Halbeek H (2000) Glycobiology 10:213

    Article  CAS  Google Scholar 

  31. Ribeirao M, Pereira-Chioccola VL, Eichinger D, Rodrigues MM, Schenkman S (1997) Glycobiology 7:1237

    Article  CAS  Google Scholar 

  32. Buschiazzo A, Tavares GA, Campetella O, Spinelli S, Cremona ML, Paris G, Amaya MF, Frasch ACC, Alzari PM (2000) EMBO J 19:16

    Article  CAS  Google Scholar 

  33. Paris G, Ratier L, Amaya MF, Nguyen T, Alzari PM, Frasch ACC (2005) J Mol Biol 345:923

    Article  CAS  Google Scholar 

  34. Lee S-G, Shin D-H, Kim B-G (2002) Enzyme Microb Technol 31:742

    Article  CAS  Google Scholar 

  35. Neubacher B, Schmidt D, Ziegelmüller P, Thiem J (2005) Org Biomol Chem 3:1551

    Article  CAS  Google Scholar 

  36. Neubacher B (2005) Chemoenzymatic syntheses of complex oligosaccharides employing trans-sialidase from Trypanosoma cruzi. PhD thesis, University of Hamburg

    Google Scholar 

  37. Ito Y, Paulson JC (1993) J Am Chem Soc 115:7862

    Article  CAS  Google Scholar 

  38. Schmidt D, Sauerbrei B, Thiem J (2000) J Org Chem 65:8518

    Article  CAS  Google Scholar 

  39. Kroeger L, Thiem J (2005) J Carbohydr Chem 24:717

    Article  CAS  Google Scholar 

  40. Scheppokat AM, Gerber A, Schroven A, Meinke S, Kopitzki S, Beketow E, Thimm J, Thiem J (2010) Eur J Cell Biol 89:39

    Article  CAS  Google Scholar 

  41. Kroeger L, Scudlo A, Thiem J (2006) Adv Synth Catal 348:1217

    Article  CAS  Google Scholar 

  42. Harrison JA, Kartha KPR, Fournier EJL, Lowary TL, Malet C, Nilsson UJ, Hindsgaul O, Schenkman S, Naismith JH, Field RA (2011) Org Biomol Chem 9:1653

    Article  CAS  Google Scholar 

  43. Campo VL, Carvalho I, Da Silva CHTP, Schenkman S, Hill L, Nepogodiev SA, Field RA (2010) Chem Sci 1:507

    Article  Google Scholar 

  44. Neubacher B, Scheid S, Kelm S, Frasch AC, Meyer B, Thiem J (2006) Chembiochem 7:896

    Article  CAS  Google Scholar 

  45. Cornforth JW, Firth ME, Gottschalk A (1958) Biochem J 68:57

    CAS  Google Scholar 

  46. Nakamura M, Furuhata K, Ogura H (1988) Chem Pharm Bull 36:4807

    Article  CAS  Google Scholar 

  47. Schroven A, Meinke S, Ziegelmüller P, Thiem J (2007) Chem Eur J 13:9012

    Article  CAS  Google Scholar 

  48. Schroven A (2007) Synthesis and investigations on modified neuraminic acid donors for regio- and stereoselective sialylation with trans sialidase (Trypanosoma cruzi). PhD thesis, University of Hamburg

    Google Scholar 

  49. Lauria-Pires L, Braga MS, Vexenat AC, Nitz N, Simoes-Barbosa A, Tinoco DL, Teixeira ARL (2000) Am J Trop Med Hyg 63:111

    CAS  Google Scholar 

  50. Schofield CJ, Jannin J, Salvatella R (2006) Trends Parasitol 22:583

    Article  Google Scholar 

  51. Neres J, Bryce RA, Douglas KT (2008) Drug Discov Today 13:110

    Article  CAS  Google Scholar 

  52. Buchini S, Buschiazzo A, Withers SG (2008) Angew Chem Int Ed 47:2700

    Article  CAS  Google Scholar 

  53. Carvalho ST, Sola-Penna M, Oliveira IA, Pita S, Goncalves AS, Neves BC, Sousa FR, Freire-de-Lima L, Kurogochi M, Hinou H, Nishimura S-i, Mendonca-Previato L, Previato JO, Todeschini AR (2010) Glycobiology 20:1034

    Google Scholar 

  54. Agusti R, Paris G, Ratier L, Frasch ACC, de Lederkremer RM (2004) Glycobiology 14:659

    Article  CAS  Google Scholar 

  55. Carvalho I, Andrade P, Campo VL, Guedes PMM, Sesti-Costa R, Silva JS, Schenkman S, Dedola S, Hill L, Rejzek M, Nepogodiev SA, Field RA (2010) Bioorg Med Chem 18:2412

    Article  CAS  Google Scholar 

  56. Giorgi ME, Ratier L, Agusti R, Frasch ACC, Lederkremer RM (2010) Glycoconjugate J 27:549

    Article  CAS  Google Scholar 

  57. Meindl P, Bodo G, Palese P, Schulman J, Tuppy H (1974) Virology 58:457

    Article  CAS  Google Scholar 

  58. Streicher H, Busse H (2006) Bioorg Med Chem 14:1047

    Article  CAS  Google Scholar 

  59. Busse H, Hakoda M, Stanley M, Streicher H (2007) J Carbohydr Chem 26:159

    Article  CAS  Google Scholar 

  60. Meinke S, Thiem J (2008) Carbohydr Res 343:1824

    Article  CAS  Google Scholar 

  61. Meinke S, Schroven A, Thiem J (2011) Org Biomol Chem 9:4487

    Article  CAS  Google Scholar 

  62. Engstler M, Ferrero-Garcia MA, Parodi AJ, Schauer R, Storz-Eckerlin T, Vasella A, Witzig C, Zhu X (1994) Helv Chim Acta 77:1166

    Article  CAS  Google Scholar 

  63. Neres J, Bonnet P, Edwards PN, Kotian PL, Buschiazzo A, Alzari PM, Bryce RA, Douglas KT (2007) Bioorg Med Chem 15:2106

    Article  CAS  Google Scholar 

  64. Neres J, Brewer ML, Ratier L, Botti H, Buschiazzo A, Edwards PN, Mortenson PN, Charlton MH, Alzari PM, Frasch AC, Bryce RA, Douglas KT (2009) Bioorg Med Chem Lett 19:589

    Article  CAS  Google Scholar 

  65. Kim JH, Ryu HW, Shim JH, Park KH, Withers SG (2009) Chembiochem 10:2475

    Article  CAS  Google Scholar 

  66. Arioka S, Sakagami M, Uematsu R, Yamaguchi H, Togame H, Takemoto H, Hinou H, Nishimura S-I (2010) Bioorg Med Chem 18:1633

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Sebastian Meinke & Joachim Thiem

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  1. Sebastian Meinke
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  2. Joachim Thiem
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Correspondence to Joachim Thiem .

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Editors and Affiliations

  1. Institute for Cellular Chemistry, Hannover, Germany

    Rita Gerardy-Schahn

  2. Lille University of Science and Technology, Villeneuve d'Ascq Cedex, France

    Philippe Delannoy

  3. Institute for Glycomics, Griffith University, Southport, Queensland, Australia

    Mark von Itzstein

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Meinke, S., Thiem, J. (2012). Trypanosomal Trans-sialidases: Valuable Synthetic Tools and Targets for Medicinal Chemistry. In: Gerardy-Schahn, R., Delannoy, P., von Itzstein, M. (eds) SialoGlyco Chemistry and Biology II. Topics in Current Chemistry, vol 367. Springer, Cham. https://doi.org/10.1007/128_2012_330

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