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Synlett 2004(10): 1784-1788
DOI: 10.1055/s-2004-829563
DOI: 10.1055/s-2004-829563
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Internally Fluorescence-Quenched Sugar Nucleotides
Weitere Informationen
Received
7 April 2004
Publikationsdatum:
15. Juli 2004 (online)
Publikationsverlauf
Publikationsdatum:
15. Juli 2004 (online)
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
- 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 LigandsTeeri 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