Improved microbiological hydroxylation of sesquiterpenoids: semisynthesis, structural determination and biotransformation studies of cyclic sulfite eudesmane derivatives.
Two new cyclic sulfite eudesmane derivatives have been investigated. Their (R) and (S) sulfur configuration and the structural arrangement of their "A" rings have been assigned by means of their 13C and 1H NMR chemical shifts and have been confirmed by single-crystal X-ray analyses. Microbial-transformation of these epimer cyclic sulfites and their dihydroxyeudesmane precursor have been studied using the hydroxylating fungus Rhizopus nigricans. Increased biocatalysis rates and considerable differences in the biotransformation of both cyclic sulfite eudesmanes have been found. Promising 8alpha,11-dihydroxy derivatives have been isolated from the (S)-diastereomer bioconversion.
García-Granados
Andrés
A
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071-Granada, Spain. agarcia@ugr.es
Gutiérrez
María C
MC
Rivas
Francisco
F
D001711:Biotransformation; D018360:Crystallography, X-Ray; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D015394:Molecular Structure; D015203:Reproducibility of Results; D012233:Rhizopus / Q000737:chemistry* / Q000378:metabolism; D045787:Sesquiterpenes, Eudesmane / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013447:Sulfites / Q000737:chemistry*; D013696:Temperature; D013997:Time Factors
D045787:Sesquiterpenes, Eudesmane; D013447:Sulfites