919122-99-9Relevant articles and documents
Diastereoselective alkylation of schiff bases for the synthesis of lipidic unnatural Fmoc-protected α-amino acids
Papini, Anna Maria,Nardi, Elena,Nuti, Francesca,Uziel, Jacques,Ginanneschi, Mauro,Chelli, Mario,Brandi, Alberto
, p. 2736 - 2741 (2007/10/03)
Peptides with increased lipophilicity can cross cell membranes more easily and have longer half -life times. For these reasons, the synthesis of enantiomerically pure Fmoc-protected lipidic α-amino acids is a relevant goal. Schiff bases originating from the reaction between the two enantiomers of 2-hydroxypinan-3-one with Gly-OtBu were alkylated with a series of long alkyl halides. Diastereomeric excesses were determined by reversed-phase HPLC, under conditions carefully chosen for such lipophilic substrates. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.