Monosaccharide-based water-soluble fluorescent tags.
Monosaccharides are fluorescently labeled under microwave irradiation by N-(coumarin-3-carbonyl)benzotriazole 4. 1,2:3,4-di- O-isopropylidene-alpha- d-galactopyranose 9 gives 12 (90%), 1,2:5,6-di- O-isopropylidene- d-glucose 10 gives 13 (89%), 2,3:5,6-di- O-isopropylidene-alpha- d-mannofuranose 11 gives 14 (65%) (all by O-acylation) and 2,3,4,5-tetra- O-pivaloyl-beta- d-galactopyranosylamine 15 gives 16 (60%) (by N-acylation). Similarly, the coumarin-containing activated lysine derivatives 7 and 8 afford the l-lysine-scaffold based coumarin labeled sugars 17, 18a, b, and 19 (67-85%) which, after removal of the diisopropylidene groups, provide water-soluble fluorescent derivatives.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Cusido
Janet
J
Narindoshvili
Tamari
T
D000215:Acylation; D000475:Alkenes / Q000737:chemistry; D003374:Coumarins / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry; D012995:Solubility; D014227:Triazines / Q000737:chemistry; D014867:Water / Q000737:chemistry*
D000475:Alkenes; D003374:Coumarins; D005456:Fluorescent Dyes; D009005:Monosaccharides; D010455:Peptides; D014227:Triazines; D014867:Water; C030123:coumarin; C013658:propylene