Total structural assignment and absolute configuration of terreinol by 13C and 1H NMR.
Magn Reson Chem
; 43(3): 251-5, 2005 Mar.
Article
in En
| MEDLINE
| ID: mdl-15625725
ABSTRACT
The carbon-carbon connectivity of terreinol, a new metabolite isolated from Aspergillus terreus, and its previous (13)C assignments were confirmed by a two-dimensional INADEQUATE experiment using a few milligrams of the compound with natural (13)C abundance. The carbon-carbon correlations were determined by computational analysis (with >99% probability) of this experiment. Additionally, the absolute configuration of terreinol was achieved indirectly via its corresponding secondary alcohol by the modified Mosher method allied to conformational analysis. The shielding effect of the phenyl group of methoxytrifluoromethylphenylacetic acid (MTPA) on the substituents of the carbonylic centre gave a fully regular Deltadelta(SR) sign distribution, allowing reliable assignment of the R configuration for terreinol.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Aspergillus
/
Spiro Compounds
/
Algorithms
/
Magnetic Resonance Spectroscopy
/
Crystallography
/
Furans
Language:
En
Journal:
Magn Reson Chem
Journal subject:
QUIMICA
Year:
2005
Document type:
Article
Affiliation country:
Brazil