ABSTRACT
Incubation of a communic acid-derived synthon with Cunninghamella elegans quantitatively affords 1 beta, 3 beta- and 7 beta- monohydroxylated derivatives.
Subject(s)
Fungi/metabolism , Lactones/metabolism , Terpenes/metabolism , Cunninghamella/chemistry , Cunninghamella/metabolism , Fungi/chemistry , Hydroxylation , Lactones/chemistry , Magnetic Resonance Spectroscopy , Terpenes/chemistryABSTRACT
Incubation of confertifolin and isodrimenin with Mucor plumbeus, Aspergillus niger or Rhizopus arrhizus gave in good yields the corresponding 3 beta-hydroxy derivatives. From isodrimenin, the known natural 7 alpha-hydroxy derivative (futronolide) was also obtained and its structure was definitely established by X-ray crystallographic study of its acetate derivative.
Subject(s)
Lactones/metabolism , Crystallography, X-Ray , Fungi/metabolism , Hydroxylation , Lactones/chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular StructureABSTRACT
The fluorescent diastereoisomeric adducts formed in a precolumn derivatization reaction of enantiomeric alpha-substituted amino acids with o-phthalaldehyde and N-acetyl-L-cysteine were separated by high-performance liquid chromatography on a conventional reversed-phase column. This method was particularly efficient for the complete analytical resolution of alpha-substituted glutamic acid analogues, such as 2-methylglutamic acid, and several cyclic analogues (1-amino-1,3-dicarboxycyclohexane, 1-amino-1,3-dicarboxy-2-cyclohexene and 1-amino-1,3-dicarboxycyclopentane). The order of elution from the column was correlated with the absolute configuration of the derivatives.
