Synthesis of Internally Fluorescence-Quenched Sugar Nucleotides

Frank Schweizer; Ole Hindsgaul; Monica M. Palcic

doi:10.1055/s-2004-829563

LETTER

Synthesis of Internally Fluorescence-Quenched Sugar Nucleotides

Frank Schweizer*^a,b, Ole Hindsgaul*^a, Monica M. Palcic^a
^a Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada
^b Department of Chemistry, University of Manitoba, Winnipeg, Manitoba R3T 2N2, Canada
Fax: +1(204)4747608; e-Mail: schweize@ms.umanitoba.ca; e-Mail: hindsgaul@crc.dk;

Abstract

Alle Artikel dieser Rubrik

Abstract

The synthesis of intramolecularly quenched UDP-Gal analogues bearing a fluorescence emitter attached to the galactose moiety and a quencher on the uracil portion is described. The rate of transfer using several galactosyltransferases was examined. Our results demonstrate that galactose-modified, sugar-nucleotide-modified and double modified UDP-Gal analogues are recognized as weak substrates by three of the galactosyltransferases.

Key words

carbohydrates - nucleotides - glycosylations - enzymes - oligosaccharides

Volltext

Referenzen

References

1 Lee YC. Lee RT. Acc. Chem. Res. 1995, 28: 322

2 Elhalabi JM. Rice KG. Curr. Med. Chem. 1999, 6: 93

3a Sadler JE. Beyer TA. Oppenheimer CL. Paulson JC. Prieels J.-P. Rearick JI. Hill RL. Methods Enzymol. 1982, 83: 458

3b Palcic MM. Sujino K. Trends in Glycoscience and Glycotechnology 2001, 13: 361

4 Keshvara LM. Gosselin S. Palcic MM. Glycobiology 1993, 3: 416

5 Gosselin S. Alhussaini M. Streiff MB. Takabayashi K. Palcic MM. Anal. Biochem. 1994, 220: 92

6 See: Sujino K. Uchiyama T. Hindsgaul O. Seto NOL. Wakarchuk WW. Palcic MM. J. Am. Chem. Soc. 2000, 122: 1261 ; and references therein

7 Yaron A. Carmel A. Katchalski-Katzir E. Anal. Biochem. 1979, 95: 228

8a Mayatoshi ED. Wang GT. Krafft GA. Erickson J. Science 1990, 247: 954

8b Meldal M. Breddam K. Anal. Biochem. 1991, 195: 141

9 Bergstrom DE. Nucleosides, Nucleotides Nucleic Acids 1982, 1: 1

10 Hirota K. Isobe Y. Kitade Y. Maki Y. Synthesis 1987, 495

11 Yoshikawa M. Kato T. Takenishi T. Tetrahedron Lett. 1967, 5065

12 Wittmann V. Wong C.-H. J. Org. Chem. 1997, 62: 2144

13 Malet C. Hindsgaul O. J. Org. Chem. 1996, 61: 4649

14a Seto NOL. Palcic MM. Hindsgaul O. Bundle DR. Narang SA. Eur. J. Biochem. 1995, 234: 323

14b Seto NOL. Palcic MM. Compston CA. Li H. Bundle DR. Narang SA. J. Biol. Chem. 1997, 272: 14133

14c Seto NOL. Compston CA. Evans S. Bundle DR. Narang SA. Palcic MM. Eur. J. Biochem. 1999, 259: 770

14d Polakowski MSL. Seto NOL. Leinala E. Borisova S. Blancher A. Roubinet F. Evans SV. Palcic MM. J. Biol. Chem. 2003, 278: 12403

15 Fang YR. Sujino K. Lu A. Gregson J. Yeske R. Kamath VP. Ratcliffe RM. Shur MJ. Wakarchuk WW. Palcic MM. Carbohydrate Bioengineering, Interdisciplinary Approaches, In Chemi-enzymatic Synthesis of Toxin Binding Ligands Teeri TT. Svensson B. Gilbert HJ. Feizi T. Royal Society of Chemistry; Cambridge UK: 2002. p.127-134

16 Barker R. Olsen WK. Shaper JH. Hill RL. J. Biol. Chem. 1972, 247: 7135

17 Sando S. Kool ET. J. Am. Chem. Soc. 2002, 124: 2096

18 Washiya K. Furuike T. Nakajima F. Lee YC. Nishimura S.-I. Anal. Biochem. 2000, 283: 39