Syntheses and properties of photoactivatable sugar derivatives designed to probe the sugar-binding site of melibiose permease.
Three new photoreactive sugar analogues bearing an azido, a diazonium salt or a diazirine group as the photophore as well as a tritium atom were developed. Two of these new photoactivatable compounds gave excellent preliminary results, with a high affinity for the melibiose permease of Escherichia coli.
Ambroise
Y
Y
Service des Molécules Marquées, Département de Biologie Cellulaire et Moléculaire, CEA/Saclay, Gif sur Yvette, France.
Mioskowski
C
C
Leblanc
G
G
Rousseau
B
B
D001386:Azides / Q000138:chemical synthesis* / Q000378:metabolism*; D001389:Azirines / Q000138:chemical synthesis* / Q000378:metabolism*; D001665:Binding Sites; D050260:Carbohydrate Metabolism; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D005697:Galactosides / Q000138:chemical synthesis* / Q000378:metabolism*; D026901:Membrane Transport Proteins / Q000737:chemistry / Q000378:metabolism*; D009598:Nitrophenylgalactosides / Q000737:chemistry; D019920:Photoaffinity Labels / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D027981:Symporters
C413744:3-trifluoromethyldiazirin-3-yl galactopyranoside; C413743:4-azidophenyl galactopyranoside; D001386:Azides; D001389:Azirines; D002241:Carbohydrates; D005697:Galactosides; D026901:Membrane Transport Proteins; D019920:Photoaffinity Labels; D027981:Symporters; D009598:Nitrophenylgalactosides; C021548:melibiose permease