Avermectin biosynthesis. Intact incorporation of a diketide chain-assembly intermediate into the polyketide macrocyclic ring

Incorporation experiments in Streptomyces avermitilis with synthetic analogues of the proposed diketide intermediate support the processive mechanism of chain assembly in the biosynthesis of the polyketide core of the avermectin structure. Specific incorporation of a 13C labelled precursor was estab...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 2; pp. 327 - 330
Main Authors Dutton, Christopher J., Hooper, Antony M., Leadlay, Peter F., Staunton, James
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 1994
Elsevier
Subjects
Antibiotics (antibacterial agents, antifungal agents)
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Applied microbiology
avermectins
Biological and medical sciences
biosynthesis
Fundamental and applied biological sciences. Psychology
isotope labeling
Microbiology
precursors
Streptomyces
Streptomyces avermitilis
Actinomycetales
Reaction intermediate
Antibiotic
Streptomycetaceae
Parasiticid
Streptomyces
Avermectins
Bacteria
Actinomycetes
Biosynthesis
Macrolide
Online AccessGet full text

Cover

More Information
Summary:Incorporation experiments in Streptomyces avermitilis with synthetic analogues of the proposed diketide intermediate support the processive mechanism of chain assembly in the biosynthesis of the polyketide core of the avermectin structure. Specific incorporation of a 13C labelled precursor was established by 13C NMR; intact incorporation of two deuterium-labelled analogues was established by electrospray mass spectrometry (ESMS). The diketide analogue ( 6) incorporates intact into the polyketide core of avermectin ( 2b) showing that chain assembly follows the processive mode
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)76544-0