Stereoselective synthesis of 1-aminoalkanephosphonic acids with two chiral centers and their activity towards leucine aminopeptidase.
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.
Drag
Marcin
M
Institute of Organic Chemistry, Biochemistry and Biotechnology, University of Technology, Wroclaw, Poland.
Pawelczak
Malgorzata
M
Kafarski
Pawel
P
D019840:2-Propanol / Q000737:chemistry; D007931:Leucyl Aminopeptidase / Q000737:chemistry*; D008666:Metalloendopeptidases / Q000737:chemistry; D008956:Models, Chemical; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000378:metabolism
D063065:Organophosphonates; D007931:Leucyl Aminopeptidase; D008666:Metalloendopeptidases; D015032:Zinc; D019840:2-Propanol