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Synthesis of Free and N α ‐Fmoc‐/ N γ ‐Boc‐Protected (2 S ,4 S )‐ and (2 S ,4 R )‐4‐Aminopipecolic Acids
Author(s) -
Machetti Fabrizio,
Cordero Franca M.,
De Sarlo Francesco,
Papini Anna M.,
Alcaro Maria C.,
Brandi Alberto
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400045
Subject(s) - chemistry , enantiopure drug , reductive amination , peptide synthesis , carboxylate , peptide , amino acid , solid phase synthesis , protecting group , piperidine , stereochemistry , amination , organic chemistry , enantioselective synthesis , catalysis , biochemistry , alkyl
The preparation of (2 S ,4 S )‐ and (2 S ,4 R )‐4‐aminopipecolic acid, a conformationally constrained basic amino acid bearing orthogonal N α / N γ ‐protection suitable for solid‐phase peptide synthesis, is reported. These amino acids were synthesised from enantiopure ethyl (2 S )‐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)