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.

Microwave-assisted One-pot Synthesis of Amide Bond using WEB

2020 ◽  
Vol 7 (1) ◽  
pp. 50-59
Author(s):  
Kantharaju Kamanna ◽  
S.Y. Khatavi ◽  
P.B. Hiremath
Keyword(s):  
Carboxylic Acid ◽  
Microwave Irradiation ◽  
Primary Amine ◽  
Bond Formation ◽  
Amide Bond ◽  
Conventional Heating ◽  
Primary Amines ◽  
One Pot ◽  
Amide Bond Formation ◽  
One Pot Synthesis

Background: Amide bond plays a key role in medicinal chemistry, and the analysis of bioactive molecular database revealed that the carboxamide group appears in more than 25% of the existing database drugs. Typically amide bonds are formed from the union of carboxylic acid and amine; however, the product formation does not occur spontaneously. Several synthetic methods have been reported for amide bond formation in literature. Present work demonstrated simple and eco-friendly amide bond formation using carboxylic acid and primary amines through in situ generation of O-acylurea. The reaction was found to be more efficient, faster reaction rate; simple work-up gave pure compound isolation in moderate to excellent yield using microwave irradiation as compared to conventional heating. Methods: Developed one-pot synthesis of amide compounds using agro-waste derived greener catalyst under microwave irradiation. Results: Twenty amide bond containing organic compounds are synthesized from carboxylic acid with primary amine catalyzed by agro-waste derived medium under microwave irradiation. First, the reaction involved carboxylic acid activation using EDC.HCl, which is the required base for the neutralization and coupling. The method employed natural agro-waste derived from banana peel ash (WEB) for the coupling gave target amide product without the use of an external organic or inorganic base. Conclusion: In the present work, we demonstrated that agro-waste extract is an alternative greener catalytic medium for the condensation of organic carboxylic acid and primary amine under microwave irradiation. The method found several advantages compared to reported methods like solventfree, non-toxic, cheaper catalyst, and simple reaction condition. The final isolated product achieved chromatographically pure by simple recrystallization and did not require further purification.

A Multifunctional HBED-Type Chelator with Dual Conjugation Capabilities for Radiopharmaceutical Development

Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1795-1798
Author(s):  
Ata Makarem ◽  
Mohammadreza Kamali Sarvestani ◽  
Karel D. Klika ◽  
Klaus Kopka
Keyword(s):  
Nuclear Medicine ◽  
Carboxylic Acid ◽  
Tumor Imaging ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Amide Bond ◽  
Carboxylic Acid Groups ◽  
Amide Bond Formation ◽  
Click Coupling

Bifunctional HBED chelators are hexadentate complexing ligands (chelators) that tightly coordinate to trivalent gallium and, additionally, are able to bind to bioactive molecules. In nuclear medicine, HBED-based radiopharmaceuticals are used as powerful radiotracers for tumor imaging. Among variants of bifunctional HBED chelators, HBED-CC is the most well-known; it possesses two terminal carboxylic acid groups that are able to undergo bioconjugation by amide-bond formation. However, to permit bioconjugation through click coupling, we previously modified the structure of HBED-CC and introduced HBED-NN chelator bearing two azide functions. We have now combined the conjugation capabilities of HBED-CC and HBED-NN chelators in one molecule and have created HBED-NC, which possesses both azide and carboxylic acid groups. The advantage of HBED-NC is that it provides options for constructing either monomeric or heterodimeric radiolabeling precursors. This work describes the synthesis of HBED-NC by either of two pathways.

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.

Diethylphosphoryl-OxymaB (DEPO-B) as a Solid Coupling Reagent for Amide Bond Formation

2018 ◽  
Vol 16 (1) ◽  
pp. 30-33
Author(s):  
Ashish Kumar ◽  
Yahya E. Jad ◽  
Ayman El-Faham ◽  
Beatriz G. de la Torre ◽  
Fernando Albericio
Keyword(s):  
Bond Formation ◽  
Hydrolytic Stability ◽  
Solid Material ◽  
Amide Bond ◽  
Amide Bond Formation ◽  
Coupling Reagent

A new phosphonium based coupling reagent DEPO-B has been synthesized from 5- (hydroxyimino)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione (Oxyma B) and diethyl chlorophosphate in presence of base. It is a solid material and the hydrolytic stability and solubility was evaluated for confirming its capability for usage in automated peptide synthesizer.

A Review of Amide Bond Formation in Microwave Organic Synthesis

2014 ◽  
Vol 11 (4) ◽  
pp. 592-604 ◽  
Author(s):  
Natalia Lukasik ◽  
Ewa Wagner-Wysiecka
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Amide Bond ◽  
Amide Bond Formation

A computational study on the mechanism of ynamide-mediated amide bond formation from carboxylic acids and amines

2017 ◽  
Vol 15 (30) ◽  
pp. 6367-6374 ◽  
Author(s):  
Song-Lin Zhang ◽  
Hai-Xing Wan ◽  
Zhu-Qin Deng
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Computational Study ◽  
Bond Formation ◽  
Amide Bond ◽  
Reactivity Pattern ◽  
Amide Bond Formation ◽  
Coupling Reagent ◽  
Catalytic Effects ◽  
Acid Substrate

A detailed computational study is presented on the reaction mechanism of ynamide-mediated condensation of carboxylic acids with amines to produce amides, which elucidates the reactivity pattern of the coupling reagent ynamide and discloses crucial bifunctional catalytic effects of the carboxylic acid substrate during aminolysis.

Sign in / Sign up

Export Citation Format

Share Document