Enzymatically catalyzed synthesis of dipeptides of γ-carboxy-L-glutamic acid from benzyloxycarbonyl-γ-carboxy-DL-glutamic acid

1985 ◽  
Vol 50 (4) ◽  
pp. 878-884 ◽  
Author(s):  
Václav Čeřovský ◽  
Karel Jošt
Keyword(s):  
Amino Acids ◽  
Glutamic Acid ◽  
Protecting Groups ◽  
Enantioselective Reaction

Enantioselective reaction of benzyloxycarbonyl-γ-carboxy-DL-glutamic acid with phenylhydrazides of various amino acids and with leucine, protected with various carboxy-protecting groups, has been studied.

Enzymatic resolution of γ-carboxy-DL-glutamic acid

1984 ◽  
Vol 49 (11) ◽  
pp. 2562-2565 ◽  
Author(s):  
Václav Čeřovský ◽  
Karel Jošt
Keyword(s):  
Glutamic Acid ◽  
Optically Active ◽  
Protecting Groups ◽  
Subsequent Removal ◽  
Enzymatic Resolution ◽  
Enantioselective Reaction

Optically active γ-carboxy-L-glutamic acid was prepared by enantioselective reaction of benzyloxycarbonyl-γ-carboxy-DL-glutamic acid with phenylhydrazine, catalyzed by papain (E.C.3.4.22.2), and subsequent removal of the protecting groups from the obtained benzyloxycarbonyl-γ-carboxy-L-glutamic acid α-phenylhydrazide.

Vasopressin and oxytocin analogs with interchanged sequence of amino acids in positions 7 and 8. synthesis and biological effects

1981 ◽  
Vol 46 (9) ◽  
pp. 2136-2139 ◽  
Author(s):  
Ivo Bláha ◽  
Viktor Krchňák ◽  
Milan Zaoral
Keyword(s):  
Amino Acids ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Effects ◽  
Free Flow ◽  
Protecting Groups ◽  
Pressor Effect ◽  
Phase Synthesis ◽  
Antidiuretic Effect

p-Toluenesulfonyl-S-benzylcysteinyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteinyl-NG-p-toluenesulfanylarginyl-prolyl-glycineamide (I) and S-benzylcysteinyl-tyrosyl-isoleucyl-glutaminyl-asparaginyl-S-benzylcysteinyl-leucyl-prolyl-glycine amide (III) were prepared by solid phase synthesis. After removal of the protecting groups, closure of the disulfide ring, and purification by continuous free-flow electrophoresis [arginine7, proline8]vasopressin (II) and [leucine7, proline8]oxytocin (IV) were obtained. The antidiuretic effect of II is markedly higher than its pressor effect; IV possesses c. 6% of the uterotonic and c. 10% of the galactogogous effect of oxytocin.

ChemInform Abstract: Enantiocontrolled Synthesis of Two Amino Acids. (S)-Glutamic Acid and ( S)-2-Aminoadipic Acid.

ChemInform ◽  
2010 ◽  
Vol 25 (40) ◽  
pp. no-no
Author(s):  
S. TAKANO ◽  
T. KAMIKUBO ◽  
M. MORIYA ◽  
K. OGASAWARA
Keyword(s):  
Amino Acids ◽  
Glutamic Acid

EFFECTS OF HYPOGLYCIN A ON THE METABOLISM OF AMINO ACIDS BY LIVER SLICES

1964 ◽  
Vol 42 (1) ◽  
pp. 139-142 ◽  
Author(s):  
S. J. Patrick ◽  
L. C. Stewart
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Fatty Acid ◽  
Glutamic Acid ◽  
Rat Liver ◽  
Inhibitory Effects ◽  
Liver Slices

The effects of hypoglycin A on the metabolism of L-leucine-C14, L-alanine-C14, and L-glutamic-acid-C14 by rat liver slices have been investigated. Hypoglycin exerted markedly inhibitory effects on the conversion of leucine-C14 to fatty acid, cholesterol, and CO2. Conversion of alanine-C14 and glutamic acid-C14 to fatty acids was also inhibited by hypoglycin. No effects of hypoglycin on the conversion of C14-amino acids into protein or glycogen were demonstrated.

scholarly journals Amino Acids and Peptides. LIV. Application of 2-Adamantyl Derivatives as Protecting Groups to the Synthesis of Peptide Fragments Related to Sulfolobus solifataricus Ribnuclease. I.

1999 ◽  
Vol 47 (8) ◽  
pp. 1089-1096 ◽  
Author(s):  
Yoshio OKADA ◽  
Shima JOSHI ◽  
Noriyuki SHINTOMI ◽  
Yukihiro KONDO ◽  
Yuko TSUDA ◽  
...  
Keyword(s):  
Amino Acids ◽  
Protecting Groups ◽  
Peptide Fragments

scholarly journals Utilization in vivo of glucose and volatile fatty acids by sheep brain for the synthesis of acidic amino acids

1966 ◽  
Vol 101 (3) ◽  
pp. 591-597 ◽  
Author(s):  
R M O'Neal ◽  
R E Koeppe ◽  
E I Williams
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Glutamic Acid ◽  
Aspartic Acid ◽  
Free Amino Acids ◽  
Free Amino ◽  
Specific Activity ◽  
Tricarboxylic Acid Cycle ◽  
Sheep Brain ◽  
The Brain

1. Free glutamic acid, aspartic acid, glutamic acid from glutamine and, in some instances, the glutamic acid from glutathione and the aspartic acid from N-acetyl-aspartic acid were isolated from the brains of sheep and assayed for radioactivity after intravenous injection of [2-(14)C]glucose, [1-(14)C]acetate, [1-(14)C]butyrate or [2-(14)C]propionate. These brain components were also isolated and analysed from rats that had been given [2-(14)C]propionate. The results indicate that, as in rat brain, glucose is by far the best precursor of the free amino acids of sheep brain. 2. Degradation of the glutamate of brain yielded labelling patterns consistent with the proposal that the major route of pyruvate metabolism in brain is via acetyl-CoA, and that the short-chain fatty acids enter the brain without prior metabolism by other tissue and are metabolized in brain via the tricarboxylic acid cycle. 3. When labelled glucose was used as a precursor, glutamate always had a higher specific activity than glutamine; when labelled fatty acids were used, the reverse was true. These findings add support and complexity to the concept of the metabolic; compartmentation' of the free amino acids of brain. 4. The results from experiments with labelled propionate strongly suggest that brain metabolizes propionate via succinate and that this metabolic route may be a limited but important source of dicarboxylic acids in the brain.

The uptake of amino acids by mouse cells (strain LS) during growth in batch culture and chemostat culture: the influence of cell growth rate

1967 ◽  
Vol 168 (1013) ◽  
pp. 421-438 ◽  
Keyword(s):  
Amino Acids ◽  
Growth Rate ◽  
Amino Acid ◽  
Cell Growth ◽  
Glutamic Acid ◽  
Batch Culture ◽  
Amino Acid Uptake ◽  
Essential Amino Acids ◽  
Growth Yields ◽  
Acid Uptake

The uptake of thirteen essential amino acids by mouse LS cells in suspension culture was determined by bacteriological assay methods. Chemostat continuous-flow cultures were used to determine the effect of different cell growth rates on the quantitative amino acid requirements for growth. The growth yields of the cells ( Y = g cell dry weight produced/g amino acid utilized) were calculated for each of the essential amino acids. A mixture of the non-essential amino acids, serine, alanine and glycine increased the cell yield from the essential amino acids. The growth yields from nearly all the essential amino acids in batch culture were increased when glutamic acid was substituted for the glutamine in the medium. The growth yields from the amino acids in batch culture were much less at the beginning than at the end of the culture. The highest efficiencies of conversion of amino acids to cell material were obtained by chemostat culture. When glutamic acid largely replaced the glutamine in the medium the conversion of amino acid nitrogen to cell nitrogen was 100 % efficient (that is, the theoretical yield was obtained) at the optimum growth rate (cell doubling time, 43 h). The maximum population density a given amino acid mixture will support can be calculated from the data. It is concluded that in several routinely used tissue culture media the cell growth is limited by the amino acid supply. In batch culture glutamine was wasted by (1) its spontaneous decomposition to pyrrolidone carboxylic acid and ammonia, and (2) its enzymic breakdown to glutamic acid and ammonia, but also glutamine was used less efficiently than glutamic acid. Study of the influence of cell growth rate on amino acid uptake rates per unit mass of cells indicated that a marked change in amino acid metabolism occurred at a specific growth rate of 0.4 day -1 (cell doubling time, 43 h). With decrease in specific growth rate below 0.4 day -1 there was a marked stimulation of amino acid uptake rate per cell and essential amino acids were consumed increasingly for functions other than synthesis of cell material.

ChemInform Abstract: Amino Acids. Part 8. A Novel Synthesis of γ-Carboxy-L-glutamic Acid from L-5-Oxoproline Esters.

ChemInform ◽  
1990 ◽  
Vol 21 (40) ◽  
Author(s):  
F. EFFENBERGER ◽  
W. MUELLER ◽  
R. KELLER ◽  
W. WILD ◽  
T. ZIEGLER
Keyword(s):  
Amino Acids ◽  
Glutamic Acid ◽  
Novel Synthesis
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