Streptazolin
Encyclopedia
Streptazolin is a antibiotic
and antifungal
substance isolated in 1981 from Streptomyces
viridochromogenes.
Because of its polymerisation tendency, it is not suitable for therapeutic use. 1,4-reduction of the conjugated diene
gives dihydrostreptazolin which is stable, but has very limited microbial properties.
The first total synthesis
of (racemic
) streptazolin was achieved in 1985 with the aid of a modified Ferrier rearrangement
.
Antibiotic
An antibacterial is a compound or substance that kills or slows down the growth of bacteria.The term is often used synonymously with the term antibiotic; today, however, with increased knowledge of the causative agents of various infectious diseases, antibiotic has come to denote a broader range of...
and antifungal
Antifungal
* Antifungal medication, a medication used to treat fungal infection s such as athlete's foot , ringworm, candidiasis, etc.* Antifungal protein, a protein family* an adjective referring to a fungicide compound...
substance isolated in 1981 from Streptomyces
Streptomyces
Streptomyces is the largest genus of Actinobacteria and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described. As with the other Actinobacteria, streptomycetes are gram-positive, and have genomes with high guanine and cytosine content...
viridochromogenes.
Because of its polymerisation tendency, it is not suitable for therapeutic use. 1,4-reduction of the conjugated diene
Diene
In organic chemistry a diene or diolefin is a hydrocarbon that contains two carbon double bonds.Conjugated dienes are functional groups, with a general formula of CnH2n-2. Dienes and alkynes are functional isomers...
gives dihydrostreptazolin which is stable, but has very limited microbial properties.
The first total synthesis
Total synthesis
In organic chemistry, a total synthesis is, in principle, the complete chemical synthesis of complex organic molecules from simpler pieces, usually without the aid of biological processes. In practice, these simpler pieces are commercially available in bulk and semi-bulk quantities, and are often...
of (racemic
Racemic
In chemistry, a racemic mixture, or racemate , is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule. The first known racemic mixture was "racemic acid", which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid.- Nomenclature :A...
) streptazolin was achieved in 1985 with the aid of a modified Ferrier rearrangement
Ferrier rearrangement
The Ferrier rearrangement is an organic reaction that involves a nucleophilic substitution reaction combined with an allylic shift in a glycal . It was discovered by the carbohydrate chemist Robert J...
.