1490-08-0Relevant articles and documents
Catalytic asymmetric claisen rearrangement of enolphosphonates: Construction of vicinal tertiary and all-carbon quaternary centers
Tan, Jiajing,Cheon, Cheol-Hong,Yamamoto, Hisashi
supporting information; experimental part, p. 8264 - 8267 (2012/09/08)
A copper-catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all-carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α-ketophosphonate substituent in the products could be easily transformed into other functional groups. Copyright
α-Aminoalkylphosphonates as a tool in experimental optimisation of P1 side chain shape of potential inhibitors in S1 pocket of leucine- and neutral aminopeptidases
Drag, Marcin,Grembecka, Jolanta,Pawelczak, Malgorzata,Kafarski, Pawel
, p. 764 - 771 (2007/10/03)
The synthesis and biological activity studies of the series of structurally different α-aminoalkylphosphonates were performed in order to optimise the shape of the side chain of the potential inhibitors in S1 pocket of leucine aminopeptidase [E.C.3.4.11.1]. Analysis of a series of compounds with aromatic, aliphatic and alicyclic P1 side chains enabled to find out the structural features, optimal for that fragment of inhibitors of LAP. The most active among all investigated compounds were the phosphonic analogues of homo-tyrosine (Ki = 120:nM) and homo-phenylalanine (Ki = 140:nM), which even as racemic mixtures were better inhibitors in comparison with the best till now-phosphonic analogue of l-leucine (230 nM). Additional comparison of the inhibitory activity obtained for aminopeptidase N (APN, E.C.3.4.11.2) give insight into structural preferences of both enzymes.
