Determination of the absolute configuration of synthetic pterocarpans by chiral HPLC using on-line CD detection

S. Z. Szarvas, G. Y. Szókán, M. Hollósi, L. Kiss, S. Antus

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Resolution of synthetic racemic pterocarpans was achieved by CD monitored HPLC using a chiral stationary phase. No sign of exciton coupling was seen in the CD spectra of the pterocarpan enantiomers. The predominance of the chromane chromophore was indicated by the high intensity of the 1Lb band. The chirality of both the chromane and dihydrobenzo[b]furane chromophores was found to be governed by the second chiral sphere. An oxygen atom in pseudoaxial position at the benzylic atom of the chroman ring system gave rise to an increased third-sphere contribution and the positive sign of the 1Lb and negative sign of the 1La band. This resulted in a general positive-negative-negative sign pattern of the 1Lb, 1La and 1Bb bands of the second-eluted enantiomer of P helicity suggesting homochirality and the same absolute configuration of the chiral centers.

Original languageEnglish
Pages (from-to)535-543
Number of pages9
JournalEnantiomer
Volume5
Issue number6
Publication statusPublished - 2000

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Pterocarpans
Enantiomers
Chromophores
Chromans
High Pressure Liquid Chromatography
Atoms
Chirality
Oxygen

Keywords

  • Absolute configuration
  • Chiral liquid chromatography
  • Circular dichroism
  • On-line HPLC-CD
  • Pterocarpans

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Determination of the absolute configuration of synthetic pterocarpans by chiral HPLC using on-line CD detection. / Szarvas, S. Z.; Szókán, G. Y.; Hollósi, M.; Kiss, L.; Antus, S.

In: Enantiomer, Vol. 5, No. 6, 2000, p. 535-543.

Research output: Contribution to journalArticle

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AU - Szókán, G. Y.

AU - Hollósi, M.

AU - Kiss, L.

AU - Antus, S.

PY - 2000

Y1 - 2000

N2 - Resolution of synthetic racemic pterocarpans was achieved by CD monitored HPLC using a chiral stationary phase. No sign of exciton coupling was seen in the CD spectra of the pterocarpan enantiomers. The predominance of the chromane chromophore was indicated by the high intensity of the 1Lb band. The chirality of both the chromane and dihydrobenzo[b]furane chromophores was found to be governed by the second chiral sphere. An oxygen atom in pseudoaxial position at the benzylic atom of the chroman ring system gave rise to an increased third-sphere contribution and the positive sign of the 1Lb and negative sign of the 1La band. This resulted in a general positive-negative-negative sign pattern of the 1Lb, 1La and 1Bb bands of the second-eluted enantiomer of P helicity suggesting homochirality and the same absolute configuration of the chiral centers.

AB - Resolution of synthetic racemic pterocarpans was achieved by CD monitored HPLC using a chiral stationary phase. No sign of exciton coupling was seen in the CD spectra of the pterocarpan enantiomers. The predominance of the chromane chromophore was indicated by the high intensity of the 1Lb band. The chirality of both the chromane and dihydrobenzo[b]furane chromophores was found to be governed by the second chiral sphere. An oxygen atom in pseudoaxial position at the benzylic atom of the chroman ring system gave rise to an increased third-sphere contribution and the positive sign of the 1Lb and negative sign of the 1La band. This resulted in a general positive-negative-negative sign pattern of the 1Lb, 1La and 1Bb bands of the second-eluted enantiomer of P helicity suggesting homochirality and the same absolute configuration of the chiral centers.

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