131102-03-9Relevant articles and documents
1-Aminocyclopentane-1,2,4-tricarboxylic acids screening on glutamatergic and serotonergic systems
Gelmi, Maria Luisa,Caputo, Francesco,Clerici, Francesca,Pellegrino, Sara,Giannaccini, Gino,Betti, Laura,Fabbrini, Laura,Schmid, Lara,Palego, Lionella,Lucacchini, Antonio
, p. 7581 - 7589 (2008/04/05)
Enantiopure constrained 1-aminocyclopentane-1,2,4-tricarboxylic acids containing the glutamic acid skeleton were prepared as two diastereomers characterized by having the carboxylic groups in position two and four cis-oriented to each other and trans with respect to 1-carboxylic group and all cis-oriented carboxylic groups, respectively. A biochemical screening of activity of the above amino acids was investigated on glutamate and 5-HT receptors to find a possible metabotropic agonist, acting on the serotoninergic system.
N-Fmoc-dehydroalanine: A versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids
Burkett,Chai
, p. 6661 - 6664 (2007/10/03)
The synthesis of polymer-supported N-Fmoc-dehydroalanine starting from S-protected cysteine via an oxidation/elimination strategy is described. Cycloaddition with a range of dienes afforded a range of conformationally constrained amino acids in moderate yields. The potential applications of this methodology to combinatorial libraries is discussed. (C) 2000 Elsevier Science Ltd.
The Diels-Alder reactions of polymer bound dehydroalanine derivatives
Burkett, Brendan A.,Chai, Christina L. L.
, p. 7035 - 7038 (2007/10/03)
The synthesis and Diels-Alder cycloadditions of a number of polymer bound dehydroalanine derivatives are described. The studies compare methodologies for accessing polymer bound dehydroalanines and establish the versatility and efficiency of solid phase Diels-Alder reactions in the synthesis of carbocyclic amino acids. These studies nicely complement the growing repertoire of methodologies for the functionalisation of amino acid derivatives.
A two-step synthesis of 2-exo-substituted 2-endo-aminonorbornenes from 2-acetamidonorbornene-2-carboxylic acids
Yamazaki,Horikawa,Nishitani,Iwasaki,Okamura,Date
, p. 541 - 548 (2007/10/02)
2-exo-Substituted 2-endo-acetamidonorbornenes (3) were synthesized in a two-step procedure from 2-acetamidonorbornene-2-carboxylic acids (1, 1') with exceedingly high exo-selectivities based on a new approach involving anodic decarboxylation followed by o
Asymmetric synthesis of 2-Aminonorbornane-2-carboxylic acids by Diels-Alder reaction
Cativiela,Lopez,Mayoral
, p. 61 - 64 (2007/10/02)
Reaction of (-)-menthyl N-acetyl-α,β-dehydroalaninate with cyclopentadiene takes place with good chemical yields and diastereofacial selectivity. The cycloadducts are easily transformed into the corresponding amino acids.
ASYMMETRIC SYNTHESIS OF CYCLOALIPHATIC α-AMINO ACIDS WITH A NORBORNANE SKELETON
Cativiela, Carlos,Lopez, Pilar,Mayoral, Jose A.
, p. 379 - 388 (2007/10/02)
The asymmetric synthesis of endo and exo 2-aminonorbornane-2-carboxylic acids is carried out via the Diels-Alder reaction between cyclopentadiene and (-)-menthyl N-acetyl-α,β-dehydroalaninate.It is shown that this dienophile is more reactive than the corresponding methyl ester, which opens the way for the use of chiral N-acetyl-α,β-dehydroalaninates as dienophiles in asymmetric Diels-Alder reactions.As high diastereofacial selectivity is obtained with what was previously considered a mediocre chiral auxiliary, the acetamido group must play an important role, which is discussed.
