Lipase-catalyzed synthesis of O-lauroyl l-serinamide and O-lauroyl l-threoninamide

Enzymatic acylation of polar dipeptides: Influence of reaction media and molecular environment of functional groups

“…This study demonstrated that it was possible to O-acylate the serine when its carboxylic group was implied in an amide bond. This results was in agreement with a previous study concerning the serinamide acylation [30]. Moreover, the O !…”

“…The electro-attractor effect of the serine carboxylic group may be diminished as this group is implied in an amide bond whereas in the Lys-Ser, it is free. This dipeptide exhibits two potential acylable sites among which the Na group was difficult to acylate as mentioned in several studies [13,30].…”

“…By amidification of serine carboxyl group, Zhang et al [30] developed an enzymatic process permitting an efficient conversion of this serinamide. The chemoselectivity of the reaction was in favour of the O-acylation showing an absence of reactivity of the Na group.…”

Amino Acids, Lactic Acid and Ascorbic Acid as Raw Materials for Biocompatible Surfactants

“…The main advantages associated with the use of biocatalysts are mild reaction conditions and high enzymatic specificity, which often eliminate the need for regioselective protection of multifunctional starting materials. This point has been clearly demonstrated by a number of recent reports dealing with the application of enzymes to synthesis and/or modification of amino acids, sugar fatty acid esters, phospholipids and alkyl glycosides [40][41][42][43][44].…”

Enzymatic acylation of the polar dipeptide, carnosine: Reaction performances in organic and aqueous media

“…However, the efficiency of these processes is often limited by the availability of polar substrates because of their low solubility in organic solvents. To overcome this limitation, several authors have proposed modifying the molecular structure of the dipeptides and free amino acids by attaching a hydrophobic group, improving solubility in reaction media [21,24,27,28]. Another strategy may be to use emerging media, such as ionic liquids.…”