ChemInform Abstract: Ester Ammoniolysis: A New Enzymatic Reaction.

Abstract

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Enzymatic strategies and biocatalysts for amide bond formation: tricks of the trade outside of the ribosome

“…In principle, an enzymatic transformation involving an amine nucleophile is highly exothermic and thereby thermodynamically favorable. 60 …”

“…94–96 CalB has also been used to convert triolein (olive oil) to its corresponding oleamide by using ammonia as the acyl acceptor (Figure 10B). 60 The scope of acyl donor variability of CalB has been extensively examined, revealing the enzyme can use a diverse range of esters 97–101 as well as dialkyl and dibenzyl carbonates. 102 Intramolecular aminolysis is also possible with lipases, as PPL has been shown to catalyze the synthesis of both small lactam rings from 4- and 5- amino-alkanoic esters (Figure 10C) and macrocyclic bislactams via condensation of diamines and diesters (Figure 10D).…”

“…10B). 60 The scope of acyl donor variability of CalB has been extensively examined, revealing the enzyme can use a diverse range of esters [97][98][99][100][101] as well as dialkyl and dibenzyl carbonates. 102 Intramolecular aminolysis is also possible with lipases, as PPL has been shown to catalyze the synthesis of both small lactam rings from 4-and 5-amino-alkanoic esters (Fig.…”

Efficient method for the synthesis of fatty acid amide from soybean oil methyl ester catalysed by modified CaO

“…Nowadays, the interest in substituting petrochemical products by natural‐derived surfactants enhances the investigation of fatty acid amide based surfactants . Among these fatty acid amides, alkylol amide, such as monoethanolamide, has a high dispersion and a positive effect on the stability of W/O foam without any toxicity, which induces a pressing need for developing an efficient method to synthesise fatty acid ethanolamide …”

Racemization-free and scalable amidation of l-proline in organic media using ammonia and a biocatalyst only

“…11 Previous biocatalytic amidation efforts mostly employed lipases as catalyst transforming activated carboxylic acid derivatives, e.g. esters [12][13][14][15] and anhydrides, 16 or lipophilic substrates, such as long chain fatty acids, with amines. [17][18][19][20][21] For instance the amidation of octanoic acid was performed via the ester intermediate, since direct ammonolysis led to the formation of salts instead of the desired octanamide.…”