The preparation of (2S,4S)- and (2S,4R)-4-aminopipecolic acid, a conformationally constrained basic amino acid bearing orthogonal Nα/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.
Synthesis of free and Nalpha-Fmoc/Ngamma-Boc protected (2S, 4S)- and (2S, 4R)-4-aminopipecolic acids / F. Machetti; F. M. Cordero; F. De Sarlo; A.M. Papini; M.C. Alcaro; A. Brandi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 13:(2004), pp. 2928-2935. [10.1002/ejoc.200400045]
Synthesis of free and Nalpha-Fmoc/Ngamma-Boc protected (2S, 4S)- and (2S, 4R)-4-aminopipecolic acids
MACHETTI, FABRIZIO;CORDERO, FRANCA MARIA;F. De Sarlo;PAPINI, ANNA MARIA;M. C. Alcaro;BRANDI, ALBERTO
2004
Abstract
The preparation of (2S,4S)- and (2S,4R)-4-aminopipecolic acid, a conformationally constrained basic amino acid bearing orthogonal Nα/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.File | Dimensione | Formato | |
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