A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid

A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid

The a-amino acid (S)-5 was synthesized using in the key step a chemoselective nucleophilic substitution between a diester derived from L-aspartic acid and 2-lithium pyridine. The overall yield (13%, 5 steps) was similar to those previously described by our group for the R isomer (the first exogen full agonist of the NMDA receptors) from D-mannitol (12%, 10 steps) and by Lovey and Copper for the racemic synthesis (17%, 5 steps).

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Main Authors: Lima,Evanoel Crizanto de, Lima,Paulo G. de, Souza,Carolina C. de, Maior,Marta C. L. S., Dias,Ayres G., Costa,Paulo R. R.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2010
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000500002
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spelling oai:scielo:S0103-505320100005000022010-07-13A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acidLima,Evanoel Crizanto deLima,Paulo G. deSouza,Carolina C. deMaior,Marta C. L. S.Dias,Ayres G.Costa,Paulo R. R. stereoselective synthesis chemoselective acyl substitution aspartic acid diester neuroactive amino acid NMDA L-tryptophan metabolism The a-amino acid (S)-5 was synthesized using in the key step a chemoselective nucleophilic substitution between a diester derived from L-aspartic acid and 2-lithium pyridine. The overall yield (13%, 5 steps) was similar to those previously described by our group for the R isomer (the first exogen full agonist of the NMDA receptors) from D-mannitol (12%, 10 steps) and by Lovey and Copper for the racemic synthesis (17%, 5 steps).info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.21 n.5 20102010-01-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000500002en10.1590/S0103-50532010000500002
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country Brasil
countrycode BR
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databasecode rev-scielo-br
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region America del Sur
libraryname SciELO
language English
format Digital
author Lima,Evanoel Crizanto de
Lima,Paulo G. de
Souza,Carolina C. de
Maior,Marta C. L. S.
Dias,Ayres G.
Costa,Paulo R. R.
spellingShingle Lima,Evanoel Crizanto de
Lima,Paulo G. de
Souza,Carolina C. de
Maior,Marta C. L. S.
Dias,Ayres G.
Costa,Paulo R. R.
A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid
author_facet Lima,Evanoel Crizanto de
Lima,Paulo G. de
Souza,Carolina C. de
Maior,Marta C. L. S.
Dias,Ayres G.
Costa,Paulo R. R.
author_sort Lima,Evanoel Crizanto de
title A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid
title_short A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid
title_full A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid
title_fullStr A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid
title_full_unstemmed A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid
title_sort new and concise strategy to the enantioselective synthesis of (s)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid
description The a-amino acid (S)-5 was synthesized using in the key step a chemoselective nucleophilic substitution between a diester derived from L-aspartic acid and 2-lithium pyridine. The overall yield (13%, 5 steps) was similar to those previously described by our group for the R isomer (the first exogen full agonist of the NMDA receptors) from D-mannitol (12%, 10 steps) and by Lovey and Copper for the racemic synthesis (17%, 5 steps).
publisher Sociedade Brasileira de Química
publishDate 2010
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000500002
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