Convenient amidation of carboxyl group of carboxyphenylboronic acids

2016 ◽  
Vol 0 (0) ◽  
Author(s):  
Julia Nowak-Jary
Keyword(s):  
Bond Formation ◽  
Amide Bond ◽  
Protecting Groups ◽  
Nucleophilic Attack ◽  
Carboxyl Groups ◽  
Coupling Reagents ◽  
Mild Conditions ◽  
Amide Bond Formation ◽  
One Step ◽  
New Compounds

AbstractThe use of catalysts in the activation of carboxyl groups towards nucleophilic attack and the protection of other functional groups by suitable protecting groups are standard and necessary procedures in amide bond formation. In contrast to the usual methods, various new compounds, amides of APTES ((3-aminopropyl)triethoxysilane, 3-triethoxysilylpropylamine) and carboxyphenylboronic acids, as well as the amides of aniline and carboxyphenylboronic acids, were obtained in good yields by a one-step synthesis under mild conditions without using any coupling reagents or additional catalysts.

“Calix[4]-box” cages promote the formation of amide bonds in water in the absence of coupling reagents

2018 ◽  
Vol 54 (70) ◽  
pp. 9738-9740 ◽  
Author(s):  
Wei-Xu Feng ◽  
Liya Dai ◽  
Shao-Ping Zheng ◽  
Arie van der Lee ◽  
Cheng-Yong Su ◽  
...  
Keyword(s):  
Template Synthesis ◽  
Bond Formation ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Amide Bonds ◽  
Amide Bond Formation

Calix[4]box cages promote template synthesis via accelerated amide bond formation upon encapsulation in water.

scholarly journals Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

1976 ◽  
Vol 160 (3) ◽  
pp. 745-755 ◽  
Author(s):  
S Hayakawa ◽  
S Hashimoto ◽  
T Onaka
Keyword(s):  
Cholic Acid ◽  
Bond Formation ◽  
Valeric Acid ◽  
Amide Bond ◽  
Side Chain ◽  
Mechanism Of Formation ◽  
Partial Synthesis ◽  
Degradative Pathway ◽  
Amide Bond Formation ◽  
New Compounds

The metabolism of cholic acid (I) by Streptomyces rubescens was investigated. This organism effected ring A cleavage, side-chain shortening and amide bond formation and gave the following metabolites: (4R)-4-[4α-(2-carboxyethyl)-3aα-hexahydro-7aβ-methyl-5-oxoindan-1 β-yl]valeric acid (IIa) and its mono-amide (valeramide) (IIb); and 2,3,4,6, 6aβ,7,8,9,9aα,9bβ-decahydro-6aβ-methyl-1H-cyclopenta[f]quinoline-3,7-dione(IIIe)and its homologues with the β-oriented side chains, valeric acid, valeramide, butanone and propionic acid, in the place of the oxo group at C-7, i.e.compounds (IIIa), (IIIb), (IIIc) and (IIId) respectively. All the nitrogenous metabolites were new compounds, and their structures were established by partial synthesis except for the metabolite (IIIc). The mechanism of formation of these metabolites is considered. A degradative pathway of cholic acid (I) into the metabolites is also tentatively proposed.

scholarly journals One-Step Biocatalytic Synthesis of Sustainable Surfactants Using Selective Amide Bond Formation

2021 ◽  
Author(s):  
Max Lubberink ◽  
Christian Schnepel ◽  
Christopher Baldwin ◽  
Nicholas Turner ◽  
Sabine Flitsch
Keyword(s):  
Fatty Acids ◽  
Carboxylic Acid ◽  
Enzymatic Synthesis ◽  
Bond Formation ◽  
Amide Bond ◽  
Esterification Reaction ◽  
Amide Bond Formation ◽  
Selective Strategy ◽  
One Step ◽  
Acyl Phosphate

N-alkanoyl-N-methylglucamides (MEGAs) are non-toxic surfactants widely used in pharmaceutical and biochemical applications and hence more sustainable syntheses towards these compounds are highly desired. Here we present an aqueous, enzymatic synthesis route towards MEGAs and analogues using carboxylic acid reductase (CAR), which has been engineered to catalyse amide bond formation (CAR-A). Compared to lipase catalysed reactions, this biocatalyst is capable of selective amide bond formation between amino-polyols and fatty acids without the competing esterification reaction being observed. The wide substrate scope of CAR-A catalysed amidation was exemplified by the synthesis of 16 amides including several commercially relevant targets. The ATP co-factor could be recycled from cheap polyphosphate using a kinase. This work establishes acyl-phosphate mediated chemistry as a selective strategy for biocatalytic amide bond formation in the presence of competing alcohol functionalities.

Amide bond formation: beyond the myth of coupling reagents

2009 ◽  
Vol 38 (2) ◽  
pp. 606-631 ◽  
Author(s):  
Eric Valeur ◽  
Mark Bradley
Keyword(s):  
Bond Formation ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Amide Bond Formation

scholarly journals Microbiological degradation of bile acids. Metabolites formed from 3-(3a α-hexahydro-7a β-methyl-1,5-dioxoindan-4 α-yl) propionic acid by Streptomyces rubescens

1977 ◽  
Vol 164 (3) ◽  
pp. 715-726 ◽  
Author(s):  
S Hashimoto ◽  
S Hayakawa
Keyword(s):  
Propionic Acid ◽  
Bond Formation ◽  
Amide Bond ◽  
Side Chain ◽  
Carbonyl Groups ◽  
Dioic Acid ◽  
Amide Bond Formation ◽  
Alpha Beta ◽  
Compound Ii ◽  
New Compounds

1. The metabolism of 3-(3a alpha-hexahydro-7a beta-methyl-1,5-dioxoindan-4 alpha-yl)propionic acid (III), which is a possible precursor of 2,3,4,6,6a beta, 7,8,9,9a alpha,9b beta-decahydro-6a beta-methyl-1H-cyclopenta[f]quinoline-3,7-dione (II) formed from cholic acid (I) by streptomyces rubescens, was investigated by using the same organism. 2. This organism effected amide bond formation, reduction of the carbonyl groups, trans alpha beta-desaturation and R-oriented beta-hydroxylation of the propionic acid side chain and skeleton cleavage, and the following metabolites were isolated as these forms or their derivatives: compound (II), 1,2,3,4 a beta,-5,6,6a beta,7,8,9a alpha,9b beta-dodecahydro-6a beta -methylcyclopental[f][1]benzopyran-3,7-dione (IVa), (1R)-1,2,3,4a beta,5,6,6a beta,7,8,9.9a alpha,9b beta-dodecahydro-1-hydroxy-6a beta-methylcyclopenta[f][1]benzopyran-3,7-dione (IVb), (E)-3-(3aalpha-hexahydro-5 alpha-hydroxy-7a beta-methyl-l-oxo-indan-4 alpha-yl)prop-2-enoic acid (V), (+)-(5R)-5-methyl-4-oxo-octane-1,8-dioic acid (VI), 3-(4-hydroxy-5-methyl-2-oxo-2H-pyran-6-yl)propionic acid (VII) and 3-(3a alpha-hexahydro-1 beta-hydroxy-7a beta-methyl-5-oxoindan-4 alpha-yl)propionic acid (VIII). The metabolites (IVb), (V), (VI) and (VII) were new compounds, and their structures were established by chemical synthesis. 3. The question of whether these metabolites are true degradative intermediates is discussed, and a degradative pathway of compound (III) to the possible precursor of compound (VII), 7-carboxy-4-methyl-3,5-dioxoheptanoyl-CoA (IX), is tentatively proposed. The further degradation of compound (IX) to small fragments is also considered.

scholarly journals A CO2-Catalyzed Transamidation Reaction

2020 ◽  
Author(s):  
Yang Yang ◽  
Jian Liu ◽  
JIWOONG LEE
Keyword(s):  
Transition State ◽  
Bond Formation ◽  
Metal Catalysts ◽  
Amide Bond ◽  
Secondary Amines ◽  
Coupling Reagents ◽  
Reaction Conditions ◽  
Amide Bond Formation ◽  
Primary And Secondary Amines ◽  
Bond Formation Reactions

<div> <div> <div> <p>Amide bond formation reactions are often mediated by reactive substrates in the presence of over-stoichiometric activating reagents and/or catalysts. Here we report a CO2-promoted transamidation reaction without additive metal catalysts or coupling reagents. The reaction forms byproducts, ammonia, primary and secondary amines, which can form adducts with CO2, thereby shifting the equilibrium in the desired direction. A comparison of Hammett studies under CO2 and N2 atmospheres suggests that the reaction transition state can be stabilized by electrophilic CO2. Selective modification of peptides was demonstrated, showing that CO2 can be utilized to control the nature of the electrophilicity and nucleophilicity of reaction partners under practical reaction conditions. </p> </div> </div> </div>

scholarly journals A CO2-Catalyzed Transamidation Reaction

2020 ◽  
Author(s):  
Yang Yang ◽  
Jian Liu ◽  
JIWOONG LEE
Keyword(s):  
Transition State ◽  
Bond Formation ◽  
Metal Catalysts ◽  
Amide Bond ◽  
Secondary Amines ◽  
Coupling Reagents ◽  
Reaction Conditions ◽  
Amide Bond Formation ◽  
Primary And Secondary Amines ◽  
Bond Formation Reactions

<div> <div> <div> <p>Amide bond formation reactions are often mediated by reactive substrates in the presence of over-stoichiometric activating reagents and/or catalysts. Here we report a CO2-promoted transamidation reaction without additive metal catalysts or coupling reagents. The reaction forms byproducts, ammonia, primary and secondary amines, which can form adducts with CO2, thereby shifting the equilibrium in the desired direction. A comparison of Hammett studies under CO2 and N2 atmospheres suggests that the reaction transition state can be stabilized by electrophilic CO2. Selective modification of peptides was demonstrated, showing that CO2 can be utilized to control the nature of the electrophilicity and nucleophilicity of reaction partners under practical reaction conditions. </p> </div> </div> </div>

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