Spiro[2.2]pentane as a Dissymmetric Scaffold for Conformationally Constrained Analogues of Glutamic Acid:  Focus on Racemic 1-Aminospiro[2.2]pentyl-1,4-dicarboxylic Acids

2002 ◽  
Vol 67 (16) ◽  
pp. 5497-5507 ◽  
Author(s):  
Roberto Pellicciari ◽  
Maura Marinozzi ◽  
Emidio Camaioni ◽  
Maria del Carmen Nùnez ◽  
Gabriele Costantino ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Dicarboxylic Acids ◽  
Conformationally Constrained

Synthesis of Conformationally Constrained Glutamic Acid Homologues and Investigation of Their Pharmacological Profiles

ChemMedChem ◽  
2007 ◽  
Vol 2 (11) ◽  
pp. 1639-1647 ◽  
Author(s):  
Paola Conti ◽  
Andrea Pinto ◽  
Lucia Tamborini ◽  
Giovanni Grazioso ◽  
Giovambattista De Sarro ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Conformationally Constrained ◽  
Pharmacological Profiles

scholarly journals Strecker degradation products of aspartic and glutamic acids and their amides

2013 ◽  
Vol 19 (No. 2) ◽  
pp. 41-45 ◽  
Author(s):  
J. Rössner ◽  
J. Velíšek ◽  
F. Pudil ◽  
J. Davídek
Keyword(s):  
Amino Acids ◽  
Glutamic Acid ◽  
Aspartic Acid ◽  
Degradation Products ◽  
Dicarboxylic Acids ◽  
Reaction Products ◽  
Degradation Reactions ◽  
Strecker Aldehydes ◽  
Volatile Products ◽  
Acid Acid

Aspartic and glutamic acids, asparagine and glutamine were oxidised with either potassium peroxodisulphate or glyoxal. Nonvolatile products were derivatised and analysed by GC/FID and GC/MS. Volatile reaction products were isolated and analysed by the same methods. It was found that the degradation reactions of amino acids are complex. Amino acids are principally degraded via the corresponding a-keto acids to Strecker aldehydes (aspartic acid to oxalacetic and 3-oxopropionic acids and glutamic acid to a-ketoglutaric and 4-oxobutyric acids), which are unstable and decomposed by decarboxylation to the corresponding aldehydes. Aspartic acid also eliminates ammonia and yields fumaric acid whereas glutamic acid gives rise to an imine, pyroglutamic acid. A recombination of free radicals leads to dicarboxylic acids (succinic acid from aspartic acid, succinic, glutaric and adipic acids from glutamic acid). The major volatile products (besides the aldehydes) are lower carboxylic acids (acetic acid from aspartic acid and propionic acid acid from glutamic acid) that can at least partly arise by radical reactions. In both quality and quantity terms, a higher amount of degradation products arises by oxidation of amino acids by peroxodisulphate.

ChemInform Abstract: Synthesis and Pharmacological Evaluation of Novel Conformationally Constrained Homologues of Glutamic Acid.

ChemInform ◽  
2008 ◽  
Vol 39 (1) ◽  
Author(s):  
Paola Conti ◽  
Antonio Caligiuri ◽  
Andrea Pinto ◽  
Gabriella Roda ◽  
Lucia Tamborini ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Conformationally Constrained ◽  
Pharmacological Evaluation

ChemInform Abstract: Synthesis of Conformationally Constrained Glutamic Acid Homologues and Investigation of Their Pharmacological Profiles.

ChemInform ◽  
2008 ◽  
Vol 39 (10) ◽  
Author(s):  
Paola Conti ◽  
Andrea Pinto ◽  
Lucia Tamborini ◽  
Giovanni Grazioso ◽  
Giovambattista De Sarro ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Conformationally Constrained ◽  
Pharmacological Profiles

Synthesis of two cyclic analogs of glutamic acid: cis- and trans-pyrrolidine-2,4-dicarboxylic acids

1991 ◽  
Vol 32 (26) ◽  
pp. 3049-3050 ◽  
Author(s):  
Frano̧is Trigalo ◽  
Christophe Molliex ◽  
Brigitte Champion ◽  
Robert Azerad
Keyword(s):  
Glutamic Acid ◽  
Dicarboxylic Acids ◽  
Cis And Trans

Synthesis of Unsaturated Analogues of Glutamic Acid: Amination of Trianions From Unsaturated Dicarboxylic Acids With Chloramine

1996 ◽  
Vol 49 (7) ◽  
pp. 785 ◽  
Author(s):  
RD Allan ◽  
RK Duke ◽  
TW Hambley ◽  
GAR Johnston ◽  
KN Mewett ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Double Bond ◽  
Glutamic Acid ◽  
Dicarboxylic Acid ◽  
Dicarboxylic Acids ◽  
Space Group ◽  
Conformationally Restricted ◽  
Convenient Synthesis

Trianions can be formed from dicarboxylic acids which contain a β,γ -double bond, and amination with chloramine yields β,γ-unsaturated α-amino acids. This methodology provides a convenient synthesis of amino acids that are inaccessible by other routes. (Z)-3-Phenylthiopent-2-enedioic acid and all four stable unsaturated analogues of the conformationally restricted glutamate analogue 1-aminocyclopentane-1,3-dicarboxylic acid have been synthesized to demonstrate the applicability of the method. The structure of one of the amino acid products, (�)-cis-1-aminocyclopent-4-ene-1,3-dicarboxylic acid (7), has been determined; it crystallizes in the space group P21/c, a 9.245(24), b 8.455(2), c 9.311(3) Ǻ, β 95.00(2)°, and the structure was refined to R 0.035 for 980 F.

ChemInform Abstract: Synthesis of Two Cyclic Analogs of Glutamic Acid: cis- and trans- Pyrrolidine-2,4-dicarboxylic Acids.

ChemInform ◽  
2010 ◽  
Vol 23 (14) ◽  
pp. no-no
Author(s):  
F. TRIGALO ◽  
C. MOLLIEX ◽  
B. CHAMPION ◽  
R. AZERAD
Keyword(s):  
Glutamic Acid ◽  
Dicarboxylic Acids ◽  
Cis And Trans

Synthesis and pharmacological evaluation of novel conformationally constrained homologues of glutamic acid

2007 ◽  
Vol 42 (8) ◽  
pp. 1059-1068 ◽  
Author(s):  
Paola Conti ◽  
Antonio Caligiuri ◽  
Andrea Pinto ◽  
Gabriella Roda ◽  
Lucia Tamborini ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Conformationally Constrained ◽  
Pharmacological Evaluation
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