Preparation and use of a photoactivatable glucose-6-phosphate analogue.
A benzophenone-containing derivative of glucose-6-phosphate, 6-[(3-([2,3-3H2]-p-benzoyl dihydrocinnamidoylpropyl-1-oxy)phosphoryl]-D-glucopyranose ([3H]BZDC-Glc-6-P) was synthesized and employed to photoaffinity label proteins on intact rat liver microsomes. The use of a non-photoactivatable, UV-transparent desoxy analogue of BZDC, named p-benzyldihydrocinnamoyl (BnDC), is introduced as a general method to achieve competition when hydrophilic ligands are modified with hydrophobic photophores.
Peng
J
J
Department of Medicinal Chemistry, The University of Utah, Salt Lake City 84112-5820, USA.
Chen
P Y
PY
Marchase
R B
RB
Prestwich
G D
GD
D000818:Animals; D017920:Antiporters / Q000378:metabolism*; D019298:Glucose-6-Phosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D066298:In Vitro Techniques; D008565:Membrane Proteins / Q000378:metabolism; D008862:Microsomes, Liver / Q000378:metabolism; D009004:Monosaccharide Transport Proteins / Q000378:metabolism*; D019920:Photoaffinity Labels / Q000138:chemical synthesis*; D010777:Photochemistry; D051381:Rats; D013347:Subcellular Fractions / Q000378:metabolism
C408998:6-((3-benzoyl-2,3-dihydrocinnamidoylpropyl-1-oxy)phosphoryl)glucopyranose; D017920:Antiporters; D008565:Membrane Proteins; D009004:Monosaccharide Transport Proteins; D019920:Photoaffinity Labels; C503533:Slc37a4 protein, rat; C111261:glucose 6-phosphate(transporter); D019298:Glucose-6-Phosphate