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Development of highly potent chiral discrimination methods that solve the problems of the diastereomer method.

Ohrui H - Proc. Jpn. Acad., Ser. B, Phys. Biol. Sci. (2007)

Bottom Line: The development of highly potent chiral discrimination methods that solve the problems of the diastereomer method, in which it is impossible to discriminate the diastereomers having chiral centers separated by more than four bonds, is described.On the basis of the results obtained, a new hypothesis, Induced Chiral Fields that the achiral reversed phase can provide chiral fields depending on the structures of the eluents, is proposed to explain the significant results of separation of the diastereomers derived from newly developed chiral and fluorescent labeling reagents and optical isomers by reversed-phase HPLC, which was hitherto impossible.

View Article: PubMed Central - PubMed

Affiliation: Yokohama College of Pharmacy, Kanagawa, Japan .

ABSTRACT
The development of highly potent chiral discrimination methods that solve the problems of the diastereomer method, in which it is impossible to discriminate the diastereomers having chiral centers separated by more than four bonds, is described. On the basis of the results obtained, a new hypothesis, Induced Chiral Fields that the achiral reversed phase can provide chiral fields depending on the structures of the eluents, is proposed to explain the significant results of separation of the diastereomers derived from newly developed chiral and fluorescent labeling reagents and optical isomers by reversed-phase HPLC, which was hitherto impossible.

No MeSH data available.


Related in: MedlinePlus

Difference of the mode of interaction with the reversed phase between derivatives labeled with the nonpolar cyclohexane reagent and those labeled with polar sugar reagent.
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f17-83_127: Difference of the mode of interaction with the reversed phase between derivatives labeled with the nonpolar cyclohexane reagent and those labeled with polar sugar reagent.

Mentions: The non-polar diastereomers derived from 7 and 16 will interact with the methylene chains of the reversed phase in two ways, as shown in Fig. 17; one is cyclohexane part of the molecule directed to the mobile phase, and the other is the cyclohexane part directed to silica gel (upside down). The mechanism of chiral discrimination between the two ways will be different. Therefore, good separation of diastereomers cannot be attained.


Development of highly potent chiral discrimination methods that solve the problems of the diastereomer method.

Ohrui H - Proc. Jpn. Acad., Ser. B, Phys. Biol. Sci. (2007)

Difference of the mode of interaction with the reversed phase between derivatives labeled with the nonpolar cyclohexane reagent and those labeled with polar sugar reagent.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3756875&req=5

f17-83_127: Difference of the mode of interaction with the reversed phase between derivatives labeled with the nonpolar cyclohexane reagent and those labeled with polar sugar reagent.
Mentions: The non-polar diastereomers derived from 7 and 16 will interact with the methylene chains of the reversed phase in two ways, as shown in Fig. 17; one is cyclohexane part of the molecule directed to the mobile phase, and the other is the cyclohexane part directed to silica gel (upside down). The mechanism of chiral discrimination between the two ways will be different. Therefore, good separation of diastereomers cannot be attained.

Bottom Line: The development of highly potent chiral discrimination methods that solve the problems of the diastereomer method, in which it is impossible to discriminate the diastereomers having chiral centers separated by more than four bonds, is described.On the basis of the results obtained, a new hypothesis, Induced Chiral Fields that the achiral reversed phase can provide chiral fields depending on the structures of the eluents, is proposed to explain the significant results of separation of the diastereomers derived from newly developed chiral and fluorescent labeling reagents and optical isomers by reversed-phase HPLC, which was hitherto impossible.

View Article: PubMed Central - PubMed

Affiliation: Yokohama College of Pharmacy, Kanagawa, Japan .

ABSTRACT
The development of highly potent chiral discrimination methods that solve the problems of the diastereomer method, in which it is impossible to discriminate the diastereomers having chiral centers separated by more than four bonds, is described. On the basis of the results obtained, a new hypothesis, Induced Chiral Fields that the achiral reversed phase can provide chiral fields depending on the structures of the eluents, is proposed to explain the significant results of separation of the diastereomers derived from newly developed chiral and fluorescent labeling reagents and optical isomers by reversed-phase HPLC, which was hitherto impossible.

No MeSH data available.


Related in: MedlinePlus