475504-29-1Relevant academic research and scientific papers
Use of hydrolases for the synthesis of cyclic amino acids
Lloyd, Richard C.,Lloyd, Michael C.,Smith, Mark E. B.,Holt, Karen E.,Swift, Jonathan P.,Keene, Philip A.,Taylor, Stephen J. C.,McCague, Raymond
, p. 717 - 728 (2007/10/03)
The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. I
Chemoenzymatic synthesis of the four diastereoisomers of 4-hydroxypipecolic acid from N-acetyl-(R,S)-allylglycine: Chiral scaffolds for drug discovery
Lloyd, Richard C.,Smith, Mark E. B.,Brick, Dean,Taylor, Stephen J. C.,Chaplin, David A.,McCague, Raymond
, p. 762 - 766 (2013/09/06)
All four diastereoisomers of 4-hydroxypipecolic acid were prepared in a form conveniently protected for drug discovery applications with the use of industrially scaleable methodology. Resolution of the racemic starting material using proprietary acylases followed by an acyliminium ion cyclisation gave diastereomeric mixtures of 4-formyloxypipecolic acid, which were differentiated using an enzyme-catalysed hydrolysis. The products were separated by partition, and by following a sequence of straightforward chemical steps, the individual stereoisomers of the protected 4-hydroxypipecolates were crystallized to optical purity in 100 g quantities.
