130830-78-3Relevant academic research and scientific papers
An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles
Jones, Raymond C.F.,Howard, Kevin J.,Snaith, John S.,Blake, Alexander J.,Li, Wang-Shei,Steel, Peter J.
experimental part, p. 8925 - 8936 (2011/12/02)
Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral 4,5-dihydroimidazolium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g., naturally occurring and other optically active proline derivatives, and optically active pyrrolizidines and indolizidines.
Stereospecific synthesis of cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5-piperidinedicarboxylic acid
Arakawa, Yasushi,Yasuda, Mika,Ohnishi, Masafumi,Yoshifuji, Shigeyuki
, p. 255 - 259 (2007/10/03)
Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5- piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S,4S)-(-)-2,4-pyrrolidinedicarboxylic acid and (2R,4R)-(+)-2,4- pyrrolidinedicarboxylic acid were synthesized from (1S,4R)-(+)-2- azabicyclo[2.2.1]hept-5-en-3-one and (1R,4S)-(-)-2-azabicyclo[2.2.1]hept-5- en-3-one, respectively.
Asymmetric Synthesis of α-Amino Acids via Cationic Aza-Cope Rearrengements
Agami, Claude,Couty, Francois,Lin, Jing,Mikaeloff, Axelle,Poursoulis, Michel
, p. 7239 - 7250 (2007/10/02)
Ene-iminium intermediates resulting from reaction between glyoxal and β-amino alcohols rearrange by an aza-Cope process.Three different tandem reactions are thus carried out; their first component is this cationic rearrangement, the second step being either an iminium hydrolysis, a nucleophile-induced ene-iminium cyclization or a Mannich reaction.The last two sequences lead to homochiral proline derivatives.
Synthesis of two cyclic analogs of glutamic acid: cis- and trans-pyrrolidine-2,4-dicarboxylic acids
Trigalo, Franois,Molliex, Christophe,Champion, Brigitte,Azerad, Robert
, p. 3049 - 3050 (2007/10/19)
The tosyl ester 2 of tetraethyl 1-acetamido-4-hydroxybutane- 1,1,3,3-tetracarboxylate gave 4-methylene glutammic acid in 90% yield by refluxing with concentrated HC1. Treatment of 2 with NaOEt, then with refluxing concentrated HC1 gave a 54% yield of cis
Conformationally Defined Neurotransmitter Analogues. Selective Inhibition of Glutamate Uptake by One Pyrrolidine-2,4-dicarboxylate Diastereomer
Bridges, Richard J.,Stanley, Mark S.,Anderson, Michael W.,Cotman, Carl W.,Chamberlin, A. Richard
, p. 717 - 725 (2007/10/02)
In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared.These "conformer mimics", the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of -L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites.While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport.These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.
