Reaction of N-acylated ?-amino acids with primary amines

1978 ◽  
Vol 27 (5) ◽  
pp. 963-969
Author(s):  
G. Ya. Kondrat'eva ◽  
M. A. Aitzhanova ◽  
V. S. Bogdanov ◽  
Z. N. Ivanova
Keyword(s):  
Amino Acids ◽  
Primary Amines

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Synthesis ◽  
2021 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Petr Beier ◽  
Maryam Khalili Foumeshi ◽  
Ali Alaei ◽  
Blanka Klepetářová
Keyword(s):  
Amino Acids ◽  
Carbon Disulfide ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Primary Amines ◽  
Oxidation Reactions ◽  
Michael Addition Reaction ◽  
Synthetic Utility ◽  
Reaction Proceeds

AbstractThiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

Titration syntheses of polyaminosubstituted phthalocyanines via nucleophilic aromatic substitutions on zinc(II) 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-hexadecafluorophthalocyanine

2007 ◽  
Vol 11 (07) ◽  
pp. 537-546 ◽  
Author(s):  
Clifford C. Leznoff ◽  
Annette Hiebert ◽  
Sibel Ok
Keyword(s):  
Amino Acids ◽  
Chain Length ◽  
Secondary Amines ◽  
Primary Amines ◽  
Tertiary Butyl ◽  
Butyl Esters ◽  
Mild Conditions ◽  
Nucleophilic Aromatic Substitutions

Primary amines, secondary amines and tertiary butyl esters of amino acids are used as nucleophiles with zinc(II) hexadecafluorophthalocyanine to provide mixtures of mono and disubstituted fluorinated phthalocyanines under mild conditions, or polyaminosubstituted phthalocyanines when using the amines as solvents. Diamines give cyclic substituted phthalocyanines, binuclear or trinuclear phthalocyanines or mixtures of both types, depending on the chain length or structure of the diamine.

Use of Dansyl Derivatives and Mass Spectrometry for Identification of Biogenic Amines

1968 ◽  
Vol 14 (4) ◽  
pp. 302-309 ◽  
Author(s):  
C R Creveling ◽  
K Kondo ◽  
J W Daly
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Biogenic Amines ◽  
Primary Amines ◽  
Mass Determination ◽  
Chromatographic System ◽  
Mammalian Heart ◽  
Heart Mass ◽  
Dansyl Derivatives ◽  
Derivatives Of

Abstract A useful technic for the isolation, separation, and identification of biogenic amines as fluores ent dansyl derivatives is described. A thin-layer chromatographic system is presented for the separation of the dansyl derivatives of phenethylamines from their corresponding β-hydroxyl derivatives, of primary amines from their corresponding N-alkylated derivatives, and of the components present in an extract of mammalian heart. Mass spectrums of dansyl derivatives of various amines and amino acids are presented to illustrate parent ion mass determination. This technic was applied to the identification of various amines present in mammalian heart. Identification was based on cochromatography and identity of parent ion mass with authentic compounds. Piperidine, dimethylamine, phenethylamine, methylamine, phenethanolamine, putrescine, spermidine, spermine, and tyramine were identified.

Current theories on the pathophysiology of equine laminitis – the link between the gut and foot

2009 ◽  
Vol 2009 ◽  
pp. 243-243
Author(s):  
J Elliott
Keyword(s):  
Amino Acids ◽  
Monoamine Oxidase ◽  
Primary Amines ◽  
Acid Decarboxylase ◽  
Similar Reaction ◽  
Bacterial Fermentation ◽  
Amino Acid Decarboxylase ◽  
Produce Amino Acid ◽  
The 1960S ◽  
Hypertensive Crises

Equine laminitis is a painful debilitating condition that seems to be a product of domestication of horses associated with the practice of feeding carbohydrate rich pasture in excess of requirements, particularly in ponies. We have been working on the hypothesis that caecal bacteria, when presented with carbohydrate in large quantities tend to ferment this. Fermentation by gram positive bacteria is associated with a fall in pH of the caecal liquor. As a means of providing themselves with increased intracellular buffering capacity, these bacteria produce amino acid decarboxylase enzymes which convert amino acids present in the caecal fluid into primary amines which can act as intracellular buffers. The reason we thought this might be the case was that foods formed by bacterial fermentation processes (e.g. cheese and wines) have a high content of amines. Primary amines derived from some amino acids have vasoactive properties. In the 1960s it was recognised that human patients taking drugs that inhibit the metabolism of amines (monoamine oxidase inhibitors) could suffer from severe hypertensive crises if they ate cheese or drank red wines with high tyramine content. This so called ‘cheese effect’ is the result of the indirect sympathomimetic effect of tyramine which displaces norepinephrine from sympathetic nerve endings leading to a rise in blood pressure. Monoamine oxidase enzymes present in the epithelial cells lining the gut wall and in liver cells normally protect individuals from suffering these hypertensive crises. We wondered whether amines released from the gut in response to ingestion of excessive amounts of carbohydrate might lead to a similar reaction in ponies whereby dietary amines caused vasoconstriction of the digital vasculature, leading to the prodromal phases of laminitis.

scholarly journals Well-Defined Construction of Functional Macromolecular Architectures Based on Polymerization of Amino Acid Urethanes

Biomedicines ◽  
2020 ◽  
Vol 8 (9) ◽  
pp. 317
Author(s):  
Takeshi Endo ◽  
Atsushi Sudo
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Primary Amines ◽  
Amino Groups ◽  
Molecular Weights ◽  
Antifouling Coatings ◽  
Onium Salts ◽  
Polypeptide Synthesis ◽  
Produce Amino Acid ◽  
Derivatives Of

Polypeptide synthesis was accomplished using the urethane derivatives of amino acids as monomers, which can be easily prepared, purified, and stored at ambient temperature without the requirement for special precautions. The urethanes of amino acids are readily synthesized by the N-carbamoylation of onium salts of amino acids using diphenyl carbonate (DPC). The prepared urethanes are then efficiently cyclized to produce amino acid N-carboxyanhydrides (NCAs). Thereafter, in the presence of primary amines, the ring-opening polymerization (ROP) of NCAs is initiated using the amines, to yield polypeptides with controlled molecular weights. The polypeptides have propagating chains bearing reactive amino groups and initiating chain ends endowed with functional moieties that originate from the amines. Aiming to benefit from these interesting characteristics of the polypeptide synthesis using the urethanes of amino acids, various macromolecular architectures containing polypeptide components have been constructed and applied as biofunctional materials in highly efficient antifouling coatings against proteins and cells, as biosensors for specific molecules, and in targeted drug delivery.

A Rapid and Sensitive Method for Chiroptical Sensing of a-Amino Acids via Click-like Labeling with o-Phthaladehyde and p-Toluenethiol

2020 ◽  
Author(s):  
Bo Li ◽  
Jie Zhang ◽  
Li Li ◽  
Gong Chen
Keyword(s):  
Amino Acids ◽  
High Sensitivity ◽  
Practical Method ◽  
High Reactivity ◽  
Primary Amines ◽  
The Novel ◽  
High Throughput Experimentation ◽  
Plate Reader ◽  
Reporting Mechanism ◽  
Sensitive Method

A highly practical method for comprehensive chiroptical sensing of free a amino acids with streamlined operation and high sensitivity via dual CD/UV measurements is developed. The assay takes advantage of an efficient and selective three-component labeling reaction of primary amines with <i>o</i>-phthalaldehyde and <i>p</i>-toluenethiol reagents, to derivatize the NH<sub>2</sub> group of analytes into an isoindole chromophore. The covalent labeling generates sensitive UV and CD readouts, both of which show excellent linear relationship with the concentration of analyte. The high reactivity and the novel chromogenic reporting mechanism allow fast and accurate measurement without background interference. The sensing assay works well for a remarkably broad range of analyte concentrations, with an unprecedented lower limit at 10 micromolar. We expect this method can be readily adapted for high throughput experimentation analysis using CD instrument equipped with a multiwell plate reader.

A Rapid and Sensitive Method for Chiroptical Sensing of a-Amino Acids via Click-like Labeling with o-Phthaladehyde and p-Toluenethiol

2020 ◽  
Author(s):  
Bo Li ◽  
Jie Zhang ◽  
Li Li ◽  
Gong Chen
Keyword(s):  
Amino Acids ◽  
High Sensitivity ◽  
Practical Method ◽  
High Reactivity ◽  
Primary Amines ◽  
The Novel ◽  
High Throughput Experimentation ◽  
Plate Reader ◽  
Reporting Mechanism ◽  
Sensitive Method

A highly practical method for comprehensive chiroptical sensing of free a amino acids with streamlined operation and high sensitivity via dual CD/UV measurements is developed. The assay takes advantage of an efficient and selective three-component labeling reaction of primary amines with <i>o</i>-phthalaldehyde and <i>p</i>-toluenethiol reagents, to derivatize the NH<sub>2</sub> group of analytes into an isoindole chromophore. The covalent labeling generates sensitive UV and CD readouts, both of which show excellent linear relationship with the concentration of analyte. The high reactivity and the novel chromogenic reporting mechanism allow fast and accurate measurement without background interference. The sensing assay works well for a remarkably broad range of analyte concentrations, with an unprecedented lower limit at 10 micromolar. We expect this method can be readily adapted for high throughput experimentation analysis using CD instrument equipped with a multiwell plate reader.

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