6533b861fe1ef96bd12c4fc6
RESEARCH PRODUCT
Stereoselective synthesis of 1-aminoalkanephosphonic acids with two chiral centers and their activity towards leucine aminopeptidase
Małgorzata PawełczakMarcin DragPaweł Kafarskisubject
PharmacologyHypophosphorous acidChemistryStereochemistryOrganic ChemistryOrganophosphonatesDiastereomerAbsolute configurationMetalloendopeptidasesStereoisomerismStereoisomerismAminopeptidaseCatalysisAnalytical Chemistry2-PropanolLeucyl AminopeptidaseZincchemistry.chemical_compoundModels ChemicalDrug DiscoveryStereoselectivityLeucineChirality (chemistry)Spectroscopydescription
The stereoselective synthesis of 1-amino-2-alkylalkanephosphonic acids, namely, compounds bearing two chiral centers, was achieved by the condensation of hypophosphorous acid salts of (R)(+) or (S)(-)-N-alpha-methylbenzylamine with the appropriate aldehydes in isopropanol. Simultaneous deprotection and oxidation by the action of bromine water provided equimolar mixtures of the RS:RR and SR:SS diastereomers of desired acids. They appeared to act as moderate inhibitors of kidney leucine aminopeptidase with potency dependent on the absolute configuration of both centers of chirality.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-07-29 | Chirality |