Self-induced chiral recognition in the association of enantiomeric mixtures on silica gel chromatography

Dobashi, Akira; Motoyama, Yuuichi.; Kinoshita, Kyo.; Hara, Shoji; Fukasaku, Noboru

doi:10.1021/ac00144a043

Cited by 58 publications

(17 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A scalemic mixture of binaphthol could be split into two fractions where one contained only the optically pure enantiomer which was in excess and the other was composed of a nearly racemic mixture. Such a behavior has been reported several times in the literature for nonracemic feed on achiral support (Cundy et al, 1983;Tsai et al, 1985;Dobashi et al, 1987;Jung and Schurig, 1992;Diter et al, 1994;Kurganov, 1996;Nicoud et al, 1996;Takahata, 1996;Stephani and Cesare 1998).…”

Section: Molecular Modelingsupporting

confidence: 55%

Enantiorecognition on solid chiral selectors using microbatch technology: an example of limitation in case of strong association in the racemate

Roussel¹,

Rafii²,

Río³

et al. 2005

Biomedical Chromatography

View full text Add to dashboard Cite

When they were independently tested, the enantiomers of N,N'-bis(salicylidene)-trans-1,2-cyclohexanediamine showed a large difference in adsorption on new chiral selectors using microbatch technology. Surprisingly, when these enantiomers were applied on the same supports as a racemic mixture, no discrimination was observed even though suitable adsorption existed. When a mixture enriched in one enantiomer (scalemic mixture) was applied, the resulting supernatant contained the racemic form and the enantiomer in excess was adsorbed on the support together with a part of racemate. This behavior, which militates in favor of a strong heterochiral dimer formation in the racemate, was revealed using microbatch technology but remained hidden on classical column chromatography on chiral support. Molecular dynamics calculations corroborate this hypothesis, showing a favorite binding mode of the heterochiral dimer, which is stabilized by various inter- and intramolecular interactions. Our findings may be considered as a new limitation of microbatch technology, but they may have some inference in case of chiral amplification using the N,N'-bis(salicylidene)-trans-1,2-cyclohexanediamine enantiomers as chiral ligands.

show abstract

Section: Molecular Modelingsupporting

confidence: 55%

Enantiorecognition on solid chiral selectors using microbatch technology: an example of limitation in case of strong association in the racemate

Roussel¹,

Rafii²,

Río³

et al. 2005

Biomedical Chromatography

View full text Add to dashboard Cite

show abstract

“…3 Soon thereafter, Dreiding et al reported 4 that chromatography on silica gel of a chiral hydrindandione also gave fractions that showed dispersion of ees. The similar chromatographic behaviour of a mixture of 14 C-labeled racemic N-acetylvaline tert-butyl ester with the unlabeled (S)-enantiomer on silica gel was described by Hara et al 5 and for a cineole derivative by Carman. 6 With (aminopropyl)silica gel as the stationary phase the same chromatographic behaviour was observed for 1,1'-binaphthol, 1-anthryl-2,2,2-trifluoroethanol, N-benzoylalanine methyl ester, a benzodiazepine, and chloromezanone.…”

Section: Introductionsupporting

confidence: 57%

Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

Drabowicz¹,

Koprowski²,

Wzorek³

et al. 2017

Arkivoc

View full text Add to dashboard Cite

This review presents a comprehensive, critical treatment of all the literature data related to the phenomenon of the SDE taking place during gravity-driven achiral chromatography of scalemic compounds bearing sulfoxide and thioamide functionalities. The discussion is focused on the SDE magnitude as a function of the structure iof the compound, composition of eluent and stationary phase, including some mechanistic details. An apparent possibility of application of the SDE phenomenon via achiral chromatography as a novel, emerging unconventional enantiomeric purification technique is also discussed.

show abstract

“…In 1985, Tsai et al 3 reported that, in the case of a bicyclic monounsaturated dione, an enantiomeric excess could induce enantiomer enrichment. More recently, Dobashi et al 4 investigated the similar chromatographic behavior of a mixture of 14C-labeled racemic Nacetylvaline tert-butylester with the unlabelled (S)-enantiomer on silica gel. In 1989, Matusch and Coors5 used aminopropylsilica gel as the stationary phase for the separation of the excess enantiomer of five different molecules such as chiral shift reagents and drugs.…”

mentioning

confidence: 99%

Enantiomeric enrichment of non-racemic mixtures of binaphthol with non-chiral packings

Nicoud¹,

Jaubert²,

Rupprecht³

et al. 1996

Chirality

View full text Add to dashboard Cite

Self-induced chiral recognition in the association of enantiomeric mixtures on silica gel chromatography

Cited by 58 publications

References 14 publications

Enantiorecognition on solid chiral selectors using microbatch technology: an example of limitation in case of strong association in the racemate

Enantiorecognition on solid chiral selectors using microbatch technology: an example of limitation in case of strong association in the racemate

Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

Enantiomeric enrichment of non-racemic mixtures of binaphthol with non-chiral packings

Contact Info

Product

Resources

About