Separation of amino acid enantiomers using supported liquid membrane extraction with chiral phosphates and phosphonates

Supported liquid membrane separation of amine and amino acid derivatives with chiral esters of phosphoric acids as carriers

“…All amino compounds were obtained as racemates. Chiral phosphoric carriers 2 -7 ( Figure 2) were synthesized according to the procedures described previously [8]. Carboxymethylb-cyclodextrin, b-cyclodextrin, and hydroxypropyl-bcyclodextrin used as chiral selectors in capillary electrophoretic analysis were obtained from Sigma-Aldrich, Poland.…”

“…The main goal of this study is to seek new possibilities for enantioselective transport of amines and non-typical amino acid derivatives (Figure 1) through SLM. The previously reported results concerned the possibility of application of this type of carriers for enantioselective transport of aromatic amino acids [8]. In the presented work, the experiments were extended for non-protein amino acids, amino acid esters, or amines using the same carriers ( Figure 2).…”

“…The most important group consists of macrocyclic compounds derived from crown ethers [4]. Other possibilities include the use of chiral complexes of transition metals [5], carriers with porphyrin or sapphyrin rings [6], macrocyclic pseudopeptides [7], chiral phosphoric acids esters [8], guanidine derivatives of sterols [9], or cinchonidine [10]. Although these carriers turned out to be more or less effective chiral selectors, their further application seems to be limited due to their moderate solubility in organic solvents.…”

Chiral Separation in Preparative Scale: A Brief Overview of Membranes as Tools for Enantiomeric Separation

“…Several liquid membranes containing different types of chiral selectors, including biomacromolecules such as human serum albumin [61,62] or enzymes [63], chiral crown ethers [64,65], cyclodextrins [66][67][68], chiral small molecules [69][70][71], and calixarenes [72,73], have been reported. Chiral liquid membrane is known as the combination of membrane separation and chiral extraction technology, which can carry out an effective real-time process to extract and recover compounds by a single unit operation.…”

Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid

“…The complexation and transport of racemic mixtures with chiral receptors has been pointed out as a smooth method for enantiomeric resolution, because it requires low concentrations of the receptor, which can be recovered at the end of the process. 17 In the literature, various types of chiral receptors bearing cyclodextrins (CDs), [18][19][20] tartaric acid derivatives, 21 crown ethers, [22][23][24] chiral complexes of transition metals, 25 carriers with porphyrin or sapphyrin rings, 26 macrocyclic pseudopeptides, 27 chiral phosphoric acids esters, 28,29 guanidine derivatives of sterols, 30,31 or cinchonidine, 32 have been reported on the chiral separation of amino acids. Although many calixarene derivatives have been synthesized as membrane carriers for anions, 33 cations, 34,35 and neutral molecules, [36][37][38] only a few investigations 39 have been reported for chiral guests.…”