The effect of temperature on the kinetics of enhanced amide bond formation from lactic acid and valine driven by deep eutectic solvents

2021 ◽  
Author(s):  
Yi-Ting Tsai ◽  
Cong-Wei Huang ◽  
Sheng-Sheng Yu
Keyword(s):  
Amino Acids ◽  
Lactic Acid ◽  
Bond Formation ◽  
Deep Eutectic Solvents ◽  
Amide Bond ◽  
Effect Of Temperature ◽  
Hydroxy Acids ◽  
Amide Bond Formation ◽  
Amide Exchange ◽  
Kinetics Of

Deep eutectic solvents have been found to facilitate the copolymerization of hydroxy acids and amino acids through ester-amide exchange reaction, and to drive the formation of amino acid-enriched oligomers with...

Kinetics of prebiotic depsipeptide formation from the ester–amide exchange reaction

2016 ◽  
Vol 18 (41) ◽  
pp. 28441-28450 ◽  
Author(s):  
Sheng-Sheng Yu ◽  
Ramanarayanan Krishnamurthy ◽  
Facundo M. Fernández ◽  
Nicholas V. Hud ◽  
F. Joseph Schork ◽  
...  
Keyword(s):  
Kinetic Model ◽  
Exchange Reaction ◽  
Bond Formation ◽  
Amide Bond ◽  
Amide Bond Formation ◽  
Amide Exchange ◽  
Kinetics Of

In this work, we introduce a kinetic model to study the effectiveness of ester-mediated amide bond formation under prebiotic conditions.

A simple and greener approach for the amide bond formation employing FeCl3 as a catalyst

2015 ◽  
Vol 39 (10) ◽  
pp. 7746-7749 ◽  
Author(s):  
Basavaprabhu Basavaprabhu ◽  
Krishnamurthy Muniyappa ◽  
Nageswara Rao Panguluri ◽  
Panduranga Veladi ◽  
Vommina V. Sureshbabu
Keyword(s):  
Amino Acids ◽  
Bond Formation ◽  
Amide Bond ◽  
Bromoacetic Acid ◽  
Amide Bond Formation ◽  
Glacial Acoh ◽  
Sterically Hindered

A protocol employing FeCl3 in the presence of glacial AcOH is described for the less nucleophilic aniline and its variants, bromoacetic acid and sterically hindered amino acids.

scholarly journals Unwanted hydrolysis or α/β-peptide bond formation: how long should the rate-limiting coupling step take?

RSC Advances ◽  
2019 ◽  
Vol 9 (53) ◽  
pp. 30720-30728 ◽  
Author(s):  
Viktória Goldschmidt Gőz ◽  
Adrienn Nagy ◽  
Viktor Farkas ◽  
Ernő Keszei ◽  
András Perczel
Keyword(s):  
Amino Acids ◽  
Bond Formation ◽  
Side Reaction ◽  
Peptide Bond ◽  
Amide Bond ◽  
Peptide Bond Formation ◽  
Active Esters ◽  
Amide Bond Formation ◽  
Rate Limiting ◽  
Hydrolysis Of

Parallel to the amide bond formation, the hydrolysis of the active esters of α/β-amino acids, as an unwanted side reaction limiting coupling efficacy, is studied.

scholarly journals Asymmetric biomimetic transamination of α-keto amides to peptides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Weiqi Cai ◽  
Xuelong Qiao ◽  
Hao Zhang ◽  
Bo Li ◽  
Jianhua Guo ◽  
...  
Keyword(s):  
Amino Acids ◽  
High Activity ◽  
Unnatural Amino Acids ◽  
Bond Formation ◽  
Amide Bond ◽  
Efficient Strategy ◽  
Amide Bond Formation ◽  
Axially Chiral ◽  
Catalytic Chemistry

AbstractPeptides are important compounds with broad applications in many areas. Asymmetric transamination of α-keto amides can provide an efficient strategy to synthesize peptides, however, the process has not been well developed yet and still remains a great challenge in both enzymatic and catalytic chemistry. For biological transamination, the high activity is attributed to manifold structural and electronic factors of transaminases. Based on the concept of multiple imitation of transaminases, here we report N-quaternized axially chiral pyridoxamines 1 for enantioselective transamination of α-keto amides, to produce various peptides in good yields with excellent enantio- and diastereoselectivities. The reaction is especially attractive for the synthesis of peptides made of unnatural amino acids since it doesn’t need great efforts to make chiral unnatural amino acids before amide bond formation.

(Chloromethylene)Dimethylammonium Chloride: A Highly Efficient Reagent for the Synthesis of β-Lactams from β-Amino Acids

2005 ◽  
Vol 2005 (11) ◽  
pp. 705-707 ◽  
Author(s):  
Seema Kanwar ◽  
Sain D. Sharma
Keyword(s):  
Amino Acids ◽  
Bond Formation ◽  
Water Soluble ◽  
Amide Bond ◽  
Dimethyl Formamide ◽  
Triethylamine Hydrochloride ◽  
Amide Bond Formation ◽  
Dimethylammonium Chloride ◽  
Reaction Proceeds ◽  
By Products

(Chloromethylene)dimethylammonium chloride 1, is a unique reagent that conveniently and efficiently mediates the amide bond formation in β-lactams via cyclodehydration of β-amino acids leading to β-lactam formation. The process involves the formation of a highly reactive activated ester of a β-amino acid which gets cyclised to the corresponding β-lactam in excellent yield. The reaction proceeds smoothly and cleanly as the by-products formed are the water soluble-dimethyl formamide and triethylamine hydrochloride.

scholarly journals Diffusion Enhanced Amide Bond Formation on Solid Support

2019 ◽  
Author(s):  
Johnny N Naoum ◽  
Israel Alshanski ◽  
Agata Gitlin-Domagalska ◽  
Moshe Bentolila ◽  
Chaim Gilon ◽  
...  
Keyword(s):  
Amino Acids ◽  
Bond Formation ◽  
Solid Support ◽  
Amide Bond ◽  
Coupling Reactions ◽  
Polystyrene Beads ◽  
Amide Bond Formation ◽  
The Common

Performing amino acids coupling reactions on solid support using fast overhead stirring is far more efficient than the common shaking mixing methods. Stirring does not harm the polystyrene beads and allows to decrease dramatically the amount of reagents used and wasted in these transformations.

scholarly journals Diffusion Enhanced Amide Bond Formation on Solid Support

2019 ◽  
Author(s):  
Johnny N Naoum ◽  
Israel Alshanski ◽  
Agata Gitlin-Domagalska ◽  
Moshe Bentolila ◽  
Chaim Gilon ◽  
...  
Keyword(s):  
Amino Acids ◽  
Bond Formation ◽  
Solid Support ◽  
Amide Bond ◽  
Coupling Reactions ◽  
Polystyrene Beads ◽  
Amide Bond Formation ◽  
The Common

Performing amino acids coupling reactions on solid support using fast overhead stirring is far more efficient than the common shaking mixing methods. Stirring does not harm the polystyrene beads and allows to decrease dramatically the amount of reagents used and wasted in these transformations.

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