Absolute configuration of hypothemycin and 5′-O-methylhypothemycin from Phoma sp.-a test case for solid state CD/TDDFT approach

Hidayat Hussain, Karsten Krohn, Ulrich Flörke, Barbara Schulz, Siegfried Draeger, Gennaro Pescitelli, Piero Salvadori, S. Antus, T. Kurtán

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Two metabolites, the known antitumor macrolide hypothemycin 1 and its new 5′-O-methyl ether, 5′-O-methylhypothemycin 2, and the known steroid ergosterol 3, were isolated from a Phoma sp. The structures were elucidated by means of spectroscopic data analysis, and the absolute configuration of hypothemycin 1 was confirmed by single crystal X-ray analysis in combination with the new solid-state CD/TDDFT methodology. Since the solid-state CD spectrum shows contributions from intermolecular interactions in the crystal, 1 represents a critical test case for our solid-state CD/TDDFT approach.

Original languageEnglish
Pages (from-to)925-930
Number of pages6
JournalTetrahedron Asymmetry
Volume18
Issue number8
DOIs
Publication statusPublished - May 16 2007

Fingerprint

solid state
Ergosterol
Methyl Ethers
Macrolides
configurations
steroids
metabolites
Steroids
X ray analysis
X-Rays
Metabolites
Ethers
ethers
Single crystals
methodology
Crystals
single crystals
crystals
hypothemycin
x rays

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Absolute configuration of hypothemycin and 5′-O-methylhypothemycin from Phoma sp.-a test case for solid state CD/TDDFT approach. / Hussain, Hidayat; Krohn, Karsten; Flörke, Ulrich; Schulz, Barbara; Draeger, Siegfried; Pescitelli, Gennaro; Salvadori, Piero; Antus, S.; Kurtán, T.

In: Tetrahedron Asymmetry, Vol. 18, No. 8, 16.05.2007, p. 925-930.

Research output: Contribution to journalArticle

Hussain, Hidayat ; Krohn, Karsten ; Flörke, Ulrich ; Schulz, Barbara ; Draeger, Siegfried ; Pescitelli, Gennaro ; Salvadori, Piero ; Antus, S. ; Kurtán, T. / Absolute configuration of hypothemycin and 5′-O-methylhypothemycin from Phoma sp.-a test case for solid state CD/TDDFT approach. In: Tetrahedron Asymmetry. 2007 ; Vol. 18, No. 8. pp. 925-930.
@article{436b29183bdd4605b8e15cda43e2ab72,
title = "Absolute configuration of hypothemycin and 5′-O-methylhypothemycin from Phoma sp.-a test case for solid state CD/TDDFT approach",
abstract = "Two metabolites, the known antitumor macrolide hypothemycin 1 and its new 5′-O-methyl ether, 5′-O-methylhypothemycin 2, and the known steroid ergosterol 3, were isolated from a Phoma sp. The structures were elucidated by means of spectroscopic data analysis, and the absolute configuration of hypothemycin 1 was confirmed by single crystal X-ray analysis in combination with the new solid-state CD/TDDFT methodology. Since the solid-state CD spectrum shows contributions from intermolecular interactions in the crystal, 1 represents a critical test case for our solid-state CD/TDDFT approach.",
author = "Hidayat Hussain and Karsten Krohn and Ulrich Fl{\"o}rke and Barbara Schulz and Siegfried Draeger and Gennaro Pescitelli and Piero Salvadori and S. Antus and T. Kurt{\'a}n",
year = "2007",
month = "5",
day = "16",
doi = "10.1016/j.tetasy.2007.04.005",
language = "English",
volume = "18",
pages = "925--930",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "8",

}

TY - JOUR

T1 - Absolute configuration of hypothemycin and 5′-O-methylhypothemycin from Phoma sp.-a test case for solid state CD/TDDFT approach

AU - Hussain, Hidayat

AU - Krohn, Karsten

AU - Flörke, Ulrich

AU - Schulz, Barbara

AU - Draeger, Siegfried

AU - Pescitelli, Gennaro

AU - Salvadori, Piero

AU - Antus, S.

AU - Kurtán, T.

PY - 2007/5/16

Y1 - 2007/5/16

N2 - Two metabolites, the known antitumor macrolide hypothemycin 1 and its new 5′-O-methyl ether, 5′-O-methylhypothemycin 2, and the known steroid ergosterol 3, were isolated from a Phoma sp. The structures were elucidated by means of spectroscopic data analysis, and the absolute configuration of hypothemycin 1 was confirmed by single crystal X-ray analysis in combination with the new solid-state CD/TDDFT methodology. Since the solid-state CD spectrum shows contributions from intermolecular interactions in the crystal, 1 represents a critical test case for our solid-state CD/TDDFT approach.

AB - Two metabolites, the known antitumor macrolide hypothemycin 1 and its new 5′-O-methyl ether, 5′-O-methylhypothemycin 2, and the known steroid ergosterol 3, were isolated from a Phoma sp. The structures were elucidated by means of spectroscopic data analysis, and the absolute configuration of hypothemycin 1 was confirmed by single crystal X-ray analysis in combination with the new solid-state CD/TDDFT methodology. Since the solid-state CD spectrum shows contributions from intermolecular interactions in the crystal, 1 represents a critical test case for our solid-state CD/TDDFT approach.

UR - http://www.scopus.com/inward/record.url?scp=34248660226&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34248660226&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2007.04.005

DO - 10.1016/j.tetasy.2007.04.005

M3 - Article

AN - SCOPUS:34248660226

VL - 18

SP - 925

EP - 930

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 8

ER -