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. 2009 Feb 5;11(3):633-6.
doi: 10.1021/ol802709x.

Mycangimycin, a polyene peroxide from a mutualist Streptomyces sp

Dong-Chan Oh  1 , Jarrod J Scott, Cameron R Currie, Jon Clardy
Affiliations

Mycangimycin, a polyene peroxide from a mutualist Streptomyces sp

Dong-Chan Oh et al. Org Lett. .

Abstract

A mutualist actinomycete of the southern pine beetle, Dendroctonus frontalis, produces a polyene peroxide with pronounced antifungal activity. Its structure, absolute configuration, and biological activity were determined by spectral analysis, chemical modification followed by the modified Mosher method, and growth inhibitory assays, respectively.

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Figures

Figure 1
Figure 1
(a) 3,5-Dihydroxy-icosa-7,9,11,13,15,17,19-heptaenoic acid like structure constructed by gCOSY, TOCSY, and gHMBC correlations. (b) Observed D2O exchangeable proton in DMSO-d6 and ROESYcorrelations of the conjugated polyene. (c) Key ROESY correlations of the peroxide ring.
Scheme 1
Scheme 1. Reaction Sequence for Determination of the Absolute Configuration of Mycangimycin
Figure 2
Figure 2
Delta values (ΔδS−R) in ppm for bis-S- and bis-R-MTPA esters (4a and 4b).
See this image and copyright information in PMC

References

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