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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.


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Structures of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (20) and sugar reagents.
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f15-83_127: Structures of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (20) and sugar reagents.

Mentions: In order to examine the effect of the polarity of the labeling reagents on the reversed-phase HPLC separation, 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(anthracene-2,3-dicarboximido)-β-D-glucopyranose (21), its O-benzoyl (22), and the O-methyl analog (23) were prepared as fluorescent and chiral labeling reagents (Fig. 15).22)


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)

Structures of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (20) and sugar reagents.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f15-83_127: Structures of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (20) and sugar reagents.
Mentions: In order to examine the effect of the polarity of the labeling reagents on the reversed-phase HPLC separation, 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(anthracene-2,3-dicarboximido)-β-D-glucopyranose (21), its O-benzoyl (22), and the O-methyl analog (23) were prepared as fluorescent and chiral labeling reagents (Fig. 15).22)

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