756486-12-1Relevant academic research and scientific papers
Synthesis of free and Nα-Fmoc-/Nγ-Boc- protected (2S,4S)- and (2S,4R)-4-aminopipecolic acids
Machetti, Fabrizio,Cordero, Franca M.,De Sarlo, Francesco,Papini, Anna M.,Alcaro, Maria C.,Brandi, Alberto
, p. 2928 - 2935 (2007/10/03)
The preparation of (2S,4S)- and (2S,4R)-4-aminopipecolic acid, a conformationally constrained basic amino acid bearing orthogonal N α/Nγ-protection suitable for solid-phase peptide synthesis, is reported. These amino acids were synthesised from enantiopure ethyl (2S)-4-oxo-1-(1-phenylethyl)-piperidine-2-carboxylate (1) with introduction of the side-chain amino group by reductive amination, followed by protection/deprotection of the functional groups. A mixture of Fmoc-Sly(Boc)-OH 6 and 7 was used to establish their compatibility in solid-phase peptide synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
