A novel series of milbemycin antibiotics from Streptomyces strain E225. II. Isolation, characterization, structure elucidation and solution conformations.

@article{Baker1990ANS,
  title={A novel series of milbemycin antibiotics from Streptomyces strain E225. II. Isolation, characterization, structure elucidation and solution conformations.},
  author={Geoffrey Harold Baker and Roderick J. J. Dorgan and Jeremy R. Everett and J. Douglas Hood and Mark Edward Poulton},
  journal={The Journal of antibiotics},
  year={1990},
  volume={43 9},
  pages={
          1069-76
        }
}
A novel series of milbemycin antibiotics were isolated from the fermentation broth of a Streptomyces species designated E225. The structures of the four main metabolites VM 44857 (1), VM 44864 (2), VM 44865 (3) and VM 44866 (4) were determined by NMR techniques. In addition we describe the solution conformations of the major metabolite VM 44857 (1). 

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References

SHOWING 1-10 OF 20 REFERENCES
A novel series of milbemycin antibiotics from Streptomyces strain E225. I. Discovery, fermentation and anthelmintic activity.
A novel series of milbemycin antibiotics were produced by soil isolate, strain E225 which was shown to be a Streptomyces species. The antibiotics displayed anthelmintic activity againstExpand
LL-F28249 antibiotic complex: a new family of antiparasitic macrocyclic lactones. Isolation, characterization and structures of LL-F28249 alpha, beta, gamma, lambda.
A new family of antiparasitic macrolides has been isolated from Streptomyces cyaneogriseus sp. noncyanogenus. The compounds, designated LL-F28249 alpha, beta, gamma and lambda, possess potentExpand
Milbemycins, a new family of macrolide antibiotics: fermentation, isolation and physico-chemical properties.
A search for novel insecticides has yielded the milbemycins, a new family of macrolide antibiotics with insecticidal and acaricidal activity. They are produced in submerged cultures of StreptomycesExpand
Milbemycins, a new family of macrolide antibiotics. Fermentation, isolation and physico-chemical properties of milbemycins D, E, F, G, and H.
TLDR
Physico-chemical characterization revealed that milbemycins D, E, F, G and H were new antibiotics possessing the 16-membered macrocyclic lactone with a 6,6- Membered spiroketal ring system. Expand
Structure determination of LL-F28249α, β, γ, and λ, potent antiparasitic macrolides from Streptomyces cyaneogriseus ssp. noncyanogenus
The structures of four antiparasitic macrocyclic lactones, LL-F28249α, λ, β, and γ(1)–(4) derived from the actinomycete Streptomyces cyaneogriseus ssp. noncyanogenus, were determined by spectroscopicExpand
Milbemycins, a new family of macrolide antibiotics. Fermentation, isolation, physico-chemical properties and bioconversion of milbemycins J and K.
Strain Rf-107, a mutant of Streptomyces hygroscopicus subsp. aureolacrimosus, obtained with ultraviolet irradiation, produced two new macrolide antibiotics, milbemycins J and K without production ofExpand
Milbemycins, a new family of macrolide antibiotics. Structure determination of milbemycins D, E, F, G, H, J and K.
TLDR
The milbemycins, a group of potent, broad-spectrum antiparasitic and pesticidal agents, are architecturally novel antibiotics of 16-membered macrocyclic lactone that have characteristically an isopropyl side chain at C-25 which differs from the known mil bemycin family bearing methyl or ethyl group atC-25. Expand
An investigation of the stereochemistry of a 22,23-dioxygenated milbemycin
Abstract We report NMR studies on a known 22,23-dioxygenated milbemycin which show that the 22 and 23 oxygen atoms are trans diequatorial (I) and not trans diaxial (II) as previously reported1. TheExpand
Milbemycins, a new family of macrolide antibiotics. Studies on the biosynthesis of milbemycins alpha 2, alpha 4 and D using 13C labeled precursors.
TLDR
It was shown that the methyl, ethyl and isopropyl groups at carbon 25 in milbemycins alpha 2, alpha 4 and D are derived from acetate, propionate and isobutyrate or DL-valine, respectively. Expand
CHEMICAL COMPOSITION OF CELL-WALL PREPARATIONS FROM STRAINS OF VARIOUS FORM-GENERA OF AEROBIC ACTINOMYCETES.
TLDR
Cell-wall preparations were made from more than 140 strains of aerobic actinomycetes representing most of the form-genera that have been proposed and contained as major constituents glucosamine, muramic acid, alanine, and glutamic acid. Expand
...
1
2
...