Development of Tartaric Acid Derived Chiral Guanidines and Their Application to Catalytic Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds

2013 ◽  
Vol 15 (12) ◽  
pp. 3106-3109 ◽  
Author(s):  
Liwei Zou ◽  
Baomin Wang ◽  
Hongfang Mu ◽  
Huanrui Zhang ◽  
Yuming Song ◽  
...  
Keyword(s):  
Tartaric Acid ◽  
Dicarbonyl Compounds

ChemInform Abstract: Development of Tartaric Acid Derived Chiral Guanidines and Their Application to Catalytic Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds.

ChemInform ◽  
2013 ◽  
Vol 44 (47) ◽  
pp. no-no
Author(s):  
Liwei Zou ◽  
Baomin Wang ◽  
Hongfang Mu ◽  
Huanrui Zhang ◽  
Yuming Song ◽  
...  
Keyword(s):  
Tartaric Acid ◽  
Dicarbonyl Compounds

Dicarbonyl derived post-translational modifications: chemistry bridging biology and aging-related disease

2020 ◽  
Vol 64 (1) ◽  
pp. 97-110
Author(s):  
Christian Sibbersen ◽  
Mogens Johannsen
Keyword(s):  
Mass Spectrometry ◽  
Future Research ◽  
Amino Acid Residues ◽  
Post Translational Modification ◽  
Dicarbonyl Compounds ◽  
Protein Targets ◽  
Post Translational Modifications ◽  
Reactive Protein ◽  
Glycation End Products ◽  
Direct Mass Spectrometry

Abstract In living systems, nucleophilic amino acid residues are prone to non-enzymatic post-translational modification by electrophiles. α-Dicarbonyl compounds are a special type of electrophiles that can react irreversibly with lysine, arginine, and cysteine residues via complex mechanisms to form post-translational modifications known as advanced glycation end-products (AGEs). Glyoxal, methylglyoxal, and 3-deoxyglucosone are the major endogenous dicarbonyls, with methylglyoxal being the most well-studied. There are several routes that lead to the formation of dicarbonyl compounds, most originating from glucose and glucose metabolism, such as the non-enzymatic decomposition of glycolytic intermediates and fructosyl amines. Although dicarbonyls are removed continuously mainly via the glyoxalase system, several conditions lead to an increase in dicarbonyl concentration and thereby AGE formation. AGEs have been implicated in diabetes and aging-related diseases, and for this reason the elucidation of their structure as well as protein targets is of great interest. Though the dicarbonyls and reactive protein side chains are of relatively simple nature, the structures of the adducts as well as their mechanism of formation are not that trivial. Furthermore, detection of sites of modification can be demanding and current best practices rely on either direct mass spectrometry or various methods of enrichment based on antibodies or click chemistry followed by mass spectrometry. Future research into the structure of these adducts and protein targets of dicarbonyl compounds may improve the understanding of how the mechanisms of diabetes and aging-related physiological damage occur.

ANTIPHYTOPATHOGENIC EFFECT OF TARTARIC ACID SYNTHETIC DERIVATIVES

2020 ◽  
pp. 3-6
Author(s):  
B. G. Babayan ◽  
S. A. Bagdasaryan ◽  
M. A. Melkumyan ◽  
A. R. Mikaelyan
Keyword(s):  
Tartaric Acid ◽  
Synthetic Derivatives

Enzymatic Iodination of Maleic and Fumaric Acids Diethyl Esters

2009 ◽  
Vol 59 (12) ◽  
pp. 1400-1404
Author(s):  
Marius Tudorascu ◽  
Spiridon Oprea ◽  
Afrodita Doina Marculescu ◽  
Stefania Tudorascu
Keyword(s):  
Hydrogen Peroxide ◽  
Tartaric Acid ◽  
Disperse System ◽  
Hydrogen Peroxide Solution ◽  
Ultrasonic Pretreatment ◽  
Tartaric Acids ◽  
Inactive Form ◽  
Generating System ◽  
Sole Product

The mechanism of the enzymatic iodination process of diethylmaleate and diethylfumarate (which present no miscibility with water) in the presence of lactoperoxidase, both in diluted hydrogen peroxide solution and in a generating system of hydrogen peroxide using ammonium and calcium iodides as halide sources in disperse system (after an ultrasonic pretreatment) was studied. The obtained sole product (diethyl-2, 3-diiodosuccinate) after the enzymatic iodination process was directly hydrolyzed to a tartaric acid present in an optically inactive form. The mechanism of obtaining the intermediate and final products and respectively, the existence of both D, L-tartaric acid and meso-tartaric acids (as lithium bitartrates) were also investigated.

Synthesis and Kinetics of Highly Substituted Piperidines in the Presence of Tartaric Acid as a Catalyst

2018 ◽  
Vol 21 (4) ◽  
pp. 302-311
Author(s):  
Younes Ghalandarzehi ◽  
Mehdi Shahraki ◽  
Sayyed M. Habibi-Khorassani
Keyword(s):  
Ambient Temperature ◽  
Tartaric Acid ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Rate Determining Step ◽  
State Approximation ◽  
Solvent Free Conditions ◽  
Steady State Approximation ◽  
Absorbance Changes ◽  
The One

Aim & Scope: The synthesis of highly substituted piperidine from the one-pot reaction between aromatic aldehydes, anilines and β-ketoesters in the presence of tartaric acid as a catalyst has been investigated in both methanol and ethanol media at ambient temperature. Different conditions of temperature and solvent were employed for calculating the thermodynamic parameters and obtaining an experimental approach to the kinetics and mechanism. Experiments were carried out under different temperature and solvent conditions. Material and Methods: Products were characterized by comparison of physical data with authentic samples and spectroscopic data (IR and NMR). Rate constants are presented as an average of several kinetic runs (at least 6-10) and are reproducible within ± 3%. The overall rate of reaction is followed by monitoring the absorbance changes of the products versus time on a Varian (Model Cary Bio- 300) UV-vis spectrophotometer with a 10 mm light-path cell. Results: The best result was achieved in the presence of 0.075 g (0.1 M) of catalyst and 5 mL methanol at ambient temperature. When the reaction was carried out under solvent-free conditions, the product was obtained in a moderate yield (25%). Methanol was optimized as a desirable solvent in the synthesis of piperidine, nevertheless, ethanol in a kinetic investigation had none effect on the enhancement of the reaction rate than methanol. Based on the spectral data, the overall order of the reaction followed the second order kinetics. The results showed that the first step of the reaction mechanism is a rate determining step. Conclusion: The use of tartaric acid has many advantages such as mild reaction conditions, simple and readily available precursors and inexpensive catalyst. The proposed mechanism was confirmed by experimental results and a steady state approximation.

Influence of substrate on modified oscillation reactions of the Belousov-Zhabotinskii type

1983 ◽  
Vol 48 (11) ◽  
pp. 3223-3228 ◽  
Author(s):  
Peter Ševčík ◽  
Ľubica Adamčíková
Keyword(s):  
Oxalic Acid ◽  
Kinetic Parameters ◽  
Tartaric Acid ◽  
Bz Reaction ◽  
Oscillation Cycle ◽  
Influence Of Substrate

The kinetic parameters of the reaction steps of the oscillation cycle and the parameters of modified oscillation reactions of the Belousov-Zhabotinskii (BZ) type with oxalic acid, tartaric acid, and hypophosphite ions were compared with predictions of Edelson's analysis based on the mechanism of the classical BZ reaction.

ChemInform Abstract: CONDENSATION OF O-AMINOPHENOL AND α-DICARBONYL COMPOUNDS. PART 1. BENZOXAZINES

1978 ◽  
Vol 9 (18) ◽  
Author(s):  
E. BELGODERE ◽  
R. BOSSIO ◽  
V. PARRINI ◽  
R. PEPINO
Keyword(s):  
Dicarbonyl Compounds

scholarly journals Stereoselective Tandem Iridium-Catalyzed Alkene Isomerization-Cope Rearrangement of ω-diene Epoxides: Efficient Access to Acyclic 1,6-Dicarbonyl Compounds

2021 ◽  
Author(s):  
Rahul Suresh ◽  
Itai Massad ◽  
Ilan Marek
Keyword(s):  
Bond Cleavage ◽  
Cope Rearrangement ◽  
Dicarbonyl Compounds ◽  
Alkene Isomerization ◽  
Efficient Access

The Cope rearrangement of 2,3-divinyloxiranes, a rare example of epoxide C-C bond cleavage, results in 4,5-dihydrooxepines which are amenable to hydrolysis, furnishing 1,6-dicarbonyl compounds containing two contiguous stereocenters at the 3- and 4- positions. We employ...

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