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4 Aminobutyric Acid

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Dieter Rewicki – One of the best experts on this subject based on the ideXlab platform.

Roland Tressl – One of the best experts on this subject based on the ideXlab platform.

  • Mechanistic Studies on the Formation of Maillard Products from [1-13C]-D-Fructose
    Maillard Reactions in Chemistry Food and Health, 2005
    Co-Authors: Dieter Rewicki, Evelyn Kersten, Bernd Helak, C. Nittka, Roland Tressl
    Abstract:

    Ketoses are known to react with amino compounds via ketimines to form the so-called Heyns compounds (2-aminoaldoses), which are assumed to undergo subsequent transformations parallel to those observed with the corresponding Amadori compounds. Until now, this assumption was not established by separate mechanistic studies. Therefore, we prepared [1- 13 C]-D-fructose from [1- 13 C]-D-glucose by enzymatic methods. In a series of model experiments [1- 13 C]-D-fructose was heated with 4Aminobutyric Acid (Strecker inactive), L-isoleucine (Strecker active), and L-proline (secondary amine type), respectively. The labeled products were analyzed by capillary GC/MS and NMR spectroscopy and the labeling characteristics were examined from MS data. Compared to corresponding experiments with [1- 13 C]-D-glucose, the significant results are: (1) With 4Aminobutyric Acid only trace amounts of 3-deoxyaldoketose products are formed in the D-fructose system, whereas 1-deoxydiketose products were generated in comparable amounts from D-glucose and D-fructose; and (2) With L-isoleucine both D-glucose and D-fructose form 3-deoxyaldoketose- and 1-deoxydiketose products in comparable amounts; but with D-fructose the most effective reaction is the formation of pyrazines initiated by a retro aldol cleavage into C 3 +C 3 fragments. This cleavage is also responsible for the formation of mixtures of isotopomeric products in D-fructose systems.

  • Structure and potential cross-linking reactivity of a new pentose-specific Maillard product
    Journal of Agricultural and Food Chemistry, 1994
    Co-Authors: Roland Tressl, Evelyn Kersten, Georg T. Wondrak, Dieter Rewicki
    Abstract:

    The Maillard reaction of model compounds for peptide-bound lysine (4Aminobutyric Acid, 6-aminocaproic Acid, N α -acetyl-L-lysine) with reducing sugars (D-ribose, D-xylose, D-arabinose, D-glucose, D-fructose, D-glyceraldehyde) was investigated under both stringent and mild conditions. With pentoses the corresponding ω-(dimethylmaleimido)carboxylic Acids 1-3 were identified as substantial, hitherto unknown components by GC/MS and NMR. Their structure was confirmed by synthesis. A pathway to compounds 1-3 was derived from the results of 4Aminobutyric Acid/[ 13 C]-D-arabinose isotopic labeling experiments

  • Formation of pyrroles, 2-pyrrolidones, and pyridones by heating of 4Aminobutyric Acid and reducing sugars
    Journal of Agricultural and Food Chemistry, 1993
    Co-Authors: Roland Tressl, Evelyn Kersten, Dieter Rewicki
    Abstract:

    The Maillard reaction of 4Aminobutyric Acid with reducing sugar (D-arabinose, D-glucose, L-rhamnose, D-fructose, maltose) was investigated in slightly Acidic aqueous media. Eight pyrroles, 14 2-pyrrolidones, and 2 4-pyridones were characterized and quantified by capillary GC/MS. For structure elucidation the compounds were separated by preparative GC or synthesized and investigated by MS, IR, and 1 H NMR spectroscopy. Due to a blocked Strecker degradation, the 4Aminobutyric Acid specific Maillard products are comparable to those of peptide-bound L-lysine. Thus, the title compounds generated in D-glucose and maltose/4Aminobutyric Acid model experiments are structurally related to E-pyrrolonorleucine and maltosine, respectively

S.s. Jayabalakrishnan – One of the best experts on this subject based on the ideXlab platform.

Alcira M. Del C. Batlle – One of the best experts on this subject based on the ideXlab platform.

  • Evidence that 4Aminobutyric Acid and 5-aminolevulinic Acid share a common transport system into Saccharomyces cerevisiae.
    The international journal of biochemistry & cell biology, 1995
    Co-Authors: Mariana Bermudez Moretti, Susana Correa Garcia, Mónica S. Chianelli, Eugenia Ramos, James R. Mattoon, Alcira M. Del C. Batlle
    Abstract:

    It has been previously reported that 5-aminolevulinic Acid (ALA) and 4Aminobutyric Acid (GABA) share a common permease in Saccharomyces cerevisiae (Bermudez Moretti et al., 1993). The aim of the present work was to determine the relationship between the transport of these compounds in isolated cells. Assessment of amino Acid incorporation was performed in S. cerevisiae using 14C-ALA or 3H-GABA. Initial rates of ALA incorporation in cells grown in the presence of 5 mM ALA and 5 mM GABA, were three to four times lower than in cells grown without supplements. Kinetic studies indicate that GABA competitively inhibits ALA transport. During the growth phase GABA uptake was also inhibited by 74% and 60% in the presence of ALA and GABA, respectively. These findings indicate that in S. cerevisiae the structurally related compounds, ALA and GABA, may be incorporated into the cells by a common carrcarrier protprotein. Should this occur in other lukaryotic cells it may explain the neurotoxic effect attributed to ALA in the pathogenesis of acute porphyrias.

Jordi Puiggalí – One of the best experts on this subject based on the ideXlab platform.