168034-55-7Relevant articles and documents
Facile syntheses of conformationally constrained analogues of lysine and homoglutamic acid
Barkallah, Salim,Schneider, Stephen L.,McCafferty, Dewey G.
, p. 4985 - 4987 (2007/10/03)
A facile divergent synthesis of the novel amino acid trans-4-aminoethyl-l- proline and trans-4-carboxymethyl-l-proline from commercially available trans-4-hydroxy-l-proline was developed. These conformationally constrained analogues of l-lysine and l-homoglutamic acid are useful proline templated amino acids (PTAAs) with potential applications in protein engineering and de novo protein design.
Synthesis of all four diastereoisomers of 4-(carboxymethyl)proline, a conformationally constrained analogue of 2-aminoadipic acid
Pellicciari, Roberto,Arenare, Loredana,Caprariis, Paolo De,Natalini, Benedetto,Marinozzi, Maura,Galli, Alessandro
, p. 1251 - 1258 (2007/10/02)
The dirhodium(II) tetraacetate catalysed reaction of ethyl diazoacetate with 2,3-dihydropyrrole-2,2-dicarboxylate 5 afforded the useful 2-azabicyclohexane 6.Its conversion into the proline-γ-acetic acid equivalent 9 as well as into the four isomers constituting the 4-(carboxymethyl)proline 13 (16a-19a) whose absolute configuration was established by an alternative asymmetric synthesis of two of them is described.Preliminary data concerning the affinity of compounds 16a-19a for the NMDA site of the NMDA receptor complex are also reported.
Synthesis of (2S,4S)-2-Carboxy-4-Pyrrolidine Acetic Acid, a Conformationally Constrained 2-Amino Adipic Acid Analogue
Langlois, Nicole,Rojas, Anne
, p. 2477 - 2480 (2007/10/02)
(2S,4S)-2-carboxy-4-pyrrolidine acetic acid was synthesized from (S)-pyroglutamic acid in 26 percent overall yield by a regiospecific deprotonation of the N-methoxycarbonyl benzylester 4. Key Words: pyroglutamic acid, excitatory amino-acids, alkyl bromoacetate, sodium cyanoborohydride.
