Exploitation of the Arndt-Eistert Homologation of N-Methyl-±-Amino Acids for Concomitant Ester and N-Methyl Peptide Formation

2008 ◽  
Vol 61 (2) ◽  
pp. 131 ◽  
Author(s):  
Andrew B. Hughes ◽  
Brad E. Sleebs
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Acid Formation ◽  
Wolff Rearrangement ◽  
Peptide Formation ◽  
Amide Formation

Results from studies of the Arndt–Eistert homologation of N-methyl-α-amino acids with concomitant ester and amide formation is discussed. The applicability of the use of ultrasound was investigated in the Wolff rearrangement of diazoketones for the production of esters and amides. This methodology was then applied to a novel ‘N-methyl coupling’ that allows simultaneous β-amino acid formation. Conventional ‘PyBroP N-methyl couplings’ were also performed as a comparison to establish the validity of the method.

scholarly journals Synthesis of Organic Matter in Aqueous Environments Simulating Small Bodies in the Solar System and the Effects of Minerals on Amino Acid Formation

Life ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 32
Author(s):  
Walaa Elmasry ◽  
Yoko Kebukawa ◽  
Kensei Kobayashi
Keyword(s):  
Amino Acids ◽  
Organic Matter ◽  
Amino Acid ◽  
Solar System ◽  
Acid Formation ◽  
Gel Chromatography ◽  
Small Bodies ◽  
Enhanced Production ◽  
Aqueous Environments ◽  
Heating Duration

The extraterrestrial delivery of organics to primitive Earth has been supported by many laboratory and space experiments. Minerals played an important role in the evolution of meteoritic organic matter. In this study, we simulated aqueous alteration in small bodies by using a solution mixture of H2CO and NH3 in the presence of water at 150 °C under different heating durations, which produced amino acids after acid hydrolysis. Moreover, minerals were added to the previous mixture to examine their catalyzing/inhibiting impact on amino acid formation. Without minerals, glycine was the dominant amino acid obtained at 1 d of the heating experiment, while alanine and β-alanine increased significantly and became dominant after 3 to 7 d. Minerals enhanced the yield of amino acids at short heating duration (1 d); however, they induced their decomposition at longer heating duration (7 d). Additionally, montmorillonite enhanced amino acid production at 1 d, while olivine and serpentine enhanced production at 3 d. Molecular weight distribution in the whole of the products obtained by gel chromatography showed that minerals enhanced both decomposition and combination of molecules. Our results indicate that minerals affected the formation of amino acids in aqueous environments in small Solar System bodies and that the amino acids could have different response behaviors according to different minerals.

scholarly journals Substrate specificity of l-δ-(α-aminoadipoyl)-l-cysteinyl-d-valine synthetase from Cephalosporium acremonium: demonstration of the structure of several unnatural tripeptide products

1994 ◽  
Vol 301 (2) ◽  
pp. 367-372 ◽  
Author(s):  
J E Baldwin ◽  
C Y Shiau ◽  
M F Byford ◽  
C J Schofield
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Substrate Specificity ◽  
Electrospray Ionization ◽  
Peptide Synthesis ◽  
Thiol Group ◽  
Cephalosporium Acremonium ◽  
Peptide Synthetases ◽  
Peptide Formation ◽  
Combined Use

Potential substrates for L-delta-(alpha-aminoadipoyl)-L-(cysteinyl)-D-valine (ACV) synthetase were initially identified using both the amino-acid-dependent ATP<-->pyrophosphate exchange reaction catalysed by the enzyme and the incorporation of 14C-radiolabelled cysteine and valine into potential peptide products. S-Carboxymethylcysteine was an effective substitute for alpha-aminoadipate and both allylglycine and vinylglycine could substitute for cysteine, indicating that the thiol group of cysteine is not essential for peptide formation. L-allo-Isoleucine but not L-isoleucine substituted effectively for valine. The structures of the presumed peptide products derived from these amino acids were confirmed by combined use of electrospray-ionization m.s. (e.s.m.s.) and 1H n.m.r. These results clearly indicate that, in common with other peptide synthetases, but in contrast with ribosomal peptide synthesis, ACV synthetase has a relatively broad substrate specificity.

AMINO ACID FORMATION FROM GLUCOSE IN THE ISOLATED ADRENOCORTICAL AND THYROID TISSUE OF THE RABBIT

1963 ◽  
Vol 44 (1) ◽  
pp. 128-132 ◽  
Author(s):  
Hans Hammar ◽  
Bo Hellman ◽  
Stig Larsson
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Glutamic Acid ◽  
Adrenal Cortex ◽  
Aspartic Acid ◽  
Thyroid Tissue ◽  
Acid Formation ◽  
Isoleucine Leucine ◽  
The Individual

ABSTRACT Quantitative paper-radiochromatography was used for measuring the amino acid formation from uniformly labelled 14C-glucose in slices from the isolated adrenal cortex and the thyroid. In both these organs glucose was utilized in the synthesis of the following amino acids: alanine, aspartic acid, glutamic acid, glutamine, arginine, proline, glycine and isoleucine/leucine. Distinct differences were noted in the rate of formation of the individual amino acids; the value for alanine being no less than 5 times higher in the thyroid than in the adrenocortical tissue. While TSH had no effect on the conversion of glucose in the thyroid, there was a tendency for a lower amino acid (glutamine) formation, when the adrenal cortex was incubated with ACTH.

EFFECTS OF SODIUM PHENYLPYRUVATE ON AMINO ACID FORMATION IN BRAIN

1965 ◽  
Vol 43 (7) ◽  
pp. 835-840 ◽  
Author(s):  
T. Itoh
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Brain Cortex ◽  
Acid Formation ◽  
Potassium Ions ◽  
Inhibitory Effects ◽  
High Potassium ◽  
Brain Cortex Slices ◽  
Cortex Slices ◽  
Intracellular Labelling

Rat brain cortex slices were incubated with glucose-U-C14 in normal Krebs–Ringer phosphate media and also media 105 mM in potassium ions. Intracellular labelling of amino acids, such as glutamic acid, glutamine, γ-aminobutyric acid, aspartic acid, and alanine, was estimated by radioautography according to the method of Kini and Quastel. The respiration of brain cortex slices was little affected by the presence of phenylpyruvate. However, the formation of these amino acids was strongly suppressed. Moreover, in high-potassium media, the inhibitory effects of phenylpyruvate were greatly magnified. The addition of phenylalanine had no significant effect either on the oxygen consumption or on the amino acid formation when brain cortex slices were incubated with glucose-U-C14.

Dietary intake of tryptophan tied emotion-related impulsivity in humans

2019 ◽  
pp. 1-8 ◽  
Author(s):  
Florian Javelle ◽  
Descartes Li ◽  
Philipp Zimmer ◽  
Sheri L. Johnson
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Food Intake ◽  
Essential Amino Acid ◽  
Food Habits ◽  
Psychological Disorder ◽  
Serotonin Synthesis ◽  
Amino Acid Tryptophan ◽  
Pass Through ◽  
Three Factor

Abstract. Emotion-related impulsivity, defined as the tendency to say or do things that one later regret during periods of heightened emotion, has been tied to a broad range of psychopathologies. Previous work has suggested that emotion-related impulsivity is tied to an impaired function of the serotonergic system. Central serotonin synthesis relies on the intake of the essential amino acid, tryptophan and its ability to pass through the blood brain barrier. Objective: The aim of this study was to determine the association between emotion-related impulsivity and tryptophan intake. Methods: Undergraduate participants (N = 25, 16 women, 9 men) completed a self-rated measure of impulsivity (Three Factor Impulsivity Index, TFI) and daily logs of their food intake and exercise. These data were coded using the software NutriNote to evaluate intakes of tryptophan, large neutral amino acids, vitamins B6/B12, and exercise. Results: Correlational analyses indicated that higher tryptophan intake was associated with significantly lower scores on two out of three subscales of the TFI, Pervasive Influence of Feelings scores r =  –.502, p < . 010, and (lack-of) Follow-Through scores, r =  –.407, p < . 050. Conclusion: Findings provide further evidence that emotion-related impulsivity is correlated to serotonergic indices, even when considering only food habits. It also suggests the need for more research on whether tryptophan supplements might be beneficial for impulsive persons suffering from a psychological disorder.

Purification of Antihemophilic Factor (Factor VIII) by Amino Acid Precipitation*

1964 ◽  
Vol 11 (01) ◽  
pp. 064-074 ◽  
Author(s):  
Robert H Wagner ◽  
William D McLester ◽  
Marion Smith ◽  
K. M Brinkhous
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Factor Viii ◽  
Plasma Protein ◽  
Acid Precipitation ◽  
Aminobutyric Acid ◽  
Gamma Aminobutyric Acid ◽  
Specific Procedure ◽  
Beta Alanine ◽  
Antihemophilic Factor

Summary1. The use of several amino acids, glycine, alpha-aminobutyric acid, alanine, beta-alanine, and gamma-aminobutyric acid, as plasma protein precipitants is described.2. A specific procedure is detailed for the preparation of canine antihemophilic factor (AHF, Factor VIII) in which glycine, beta-alanine, and gammaaminobutyric acid serve as the protein precipitants.3. Preliminary results are reported for the precipitation of bovine and human AHF with amino acids.

Complete Covalent Structure of Human Platelet Factor 4

1979 ◽  
Vol 42 (05) ◽  
pp. 1652-1660 ◽  
Author(s):  
Francis J Morgan ◽  
Geoffrey S Begg ◽  
Colin N Chesterman
Keyword(s):  
Amino Acids ◽  
Molecular Weight ◽  
Amino Acid ◽  
Amino Acid Sequence ◽  
Human Platelet ◽  
Platelet Factor 4 ◽  
Platelet Factor ◽  
Disulphide Bonds ◽  
Covalent Structure

SummaryThe amino acid sequence of the subunit of human platelet factor 4 has been determined. Human platelet factor 4 consists of identical subunits containing 70 amino acids, each with a molecular weight of 7,756. The molecule contains no methionine, phenylalanine or tryptophan. The proposed amino acid sequence of PF4 is: Glu-Ala-Glu-Glu-Asp-Gly-Asp-Leu-Gln-Cys-Leu-Cys-Val-Lys-Thr-Thr-Ser- Gln-Val-Arg-Pro-Arg-His-Ile-Thr-Ser-Leu-Glu-Val-Ile-Lys-Ala-Gly-Pro-His-Cys-Pro-Thr-Ala-Gin- Leu-Ile-Ala-Thr-Leu-Lys-Asn-Gly-Arg-Lys-Ile-Cys-Leu-Asp-Leu-Gln-Ala-Pro-Leu-Tyr-Lys-Lys- Ile-Ile-Lys-Lys-Leu-Leu-Glu-Ser. From consideration of the homology with p-thromboglobulin, disulphide bonds between residues 10 and 36 and between residues 12 and 52 can be inferred.

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