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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

X-ray structure of (R)-11-docosanoyl (1S,2S)-2-(anthracene-2,3-dicarboximido)cyclohexane carboxylate.
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f11-83_127: X-ray structure of (R)-11-docosanoyl (1S,2S)-2-(anthracene-2,3-dicarboximido)cyclohexane carboxylate.

Mentions: One of the characteristics of the anthracenedicarboximido reagents is that they give crystalline derivatives that are suitable for X-ray studies. The X-ray structure of the (1R, 2R)-7 ester of (S)-11-docosanol (17) is shown in Fig. 11. In Fig. 11, the shorter methylene chain of 17 is laid over the anthracenedicarboximido group to show that the preferred conformation (the 1,3-syn relationship between the carbonyl oxygen and hydrogen of the secondary alcohol and s-trans between the carbonyl oxygen and the α-hydrogen on the cyclohexane ring) continues to have a crystalline structure.


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)

X-ray structure of (R)-11-docosanoyl (1S,2S)-2-(anthracene-2,3-dicarboximido)cyclohexane carboxylate.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f11-83_127: X-ray structure of (R)-11-docosanoyl (1S,2S)-2-(anthracene-2,3-dicarboximido)cyclohexane carboxylate.
Mentions: One of the characteristics of the anthracenedicarboximido reagents is that they give crystalline derivatives that are suitable for X-ray studies. The X-ray structure of the (1R, 2R)-7 ester of (S)-11-docosanol (17) is shown in Fig. 11. In Fig. 11, the shorter methylene chain of 17 is laid over the anthracenedicarboximido group to show that the preferred conformation (the 1,3-syn relationship between the carbonyl oxygen and hydrogen of the secondary alcohol and s-trans between the carbonyl oxygen and the α-hydrogen on the cyclohexane ring) continues to have a crystalline structure.

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