77. Synthese d'une sonde biotinylee a bras clivable allonge pour l'isolement des recepteurs de l'angiotensine II

Article abstract of DOI:10.1002/hlca.19890720409

We have synthesized a new biotinylated probe for angiotensin II receptors studies; biotinyl-NH(CH2)2-SS-(CH2)2-CO-Gly-εAhx-1,Phe(4N3)⁸>angiotensin II (5).This molecule can be photoactivated through an arylazido group. 1H-NMR studies suggest that it adopts an extended conformation which should allow a simultaneous recognition of both streptavidin and hormone receptor.It has a good affinity for receptors (K_d= 1 nM) and hence is a promising tool in their detection (autoradiography, gold-, ferritin-, enzyme-, or fluorescent streptavidin derivatives) and separation (cell sorting, affinity chromatography).It can be monoiodinated <*> at its tyrosine residue without a significant loss of affinity.Its extended cleavable arm allows an easy recovery of the probe-receptor'complex from streptavidin.An HPLC monitoring of the synthesis is described, particularly of the segment coupling 1+2 in presence of (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP).This method can be used as well for synthesis of the D-Phe⁸ derivative that has antagonist properties.