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. 2009;48(4):725-7.
doi: 10.1002/anie.200804890.

The ammosamides: structures of cell cycle modulators from a marine-derived Streptomyces species

Chambers C Hughes  1 , John B MacMillan, Susana P Gaudêncio, Paul R Jensen, William Fenical
Affiliations

The ammosamides: structures of cell cycle modulators from a marine-derived Streptomyces species

Chambers C Hughes et al. Angew Chem Int Ed Engl. 2009.
No abstract available

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Figures

Figure 1
Figure 1
X-ray crystal structure of ammosamide A (1). Red O, blue N, yellow Cl, black C, white H.
Scheme 1
Scheme 1
Related metabolites from bacteria and sponges.
Scheme 2
Scheme 2
Possible tautomeric form of ammosamide A (1).
See this image and copyright information in PMC

References

    1. Fenical W, Jensen PR. Nat. Chem. Biol. 2006;2:666–673. - PubMed
    2. Koehn FE, Carter GT. Nat. Rev. Drug Discovery. 2005;4:206–220. - PubMed
    1. Feling RH, Buchanan GO, Mincer TJ, Kauffman CA, Jensen PR, Fenical W. Angew. Chem. 2003;115:369–371. - PubMed
    2. Angew. Chem. Int. Ed. 2003;42:355–357.
    3. Cho JY, Kwon HC, Williams PG, Jensen PR, Fenical W. Org. Lett. 2006;8:2471–2474. - PMC - PubMed
    4. Kwon HC, Kauffman CA, Jensen PR, Fenical W. J. Am. Chem. Soc. 2006;128:1622–1632. - PubMed

    1. Strain CNR-698 was isolated from a sediment sample collected at Little San Salvador, Bahamas. The strain does not require seawater for growth. Its partial 16S rRNA sequence (Genbank #EU863183) is 100% identical to another bacterium of the family Streptomycetaceae, also isolated from marine sediments (20 m) (#EU099411).

    1. X-ray measurements were made on a SMART CCD area detector with graphite monochromated MoKα radiation (λ=1.54178 Å). 1 (C12H10ClN5OS): crystal dimensions 0.30×0.20×0.10 mm, monoclinic, space group P21/c, a=9.3766(8), b=18.2930(12), c=7.0462(6) Å, V=1208.55(17) Å3, Z=4, ρcalcd=1.691 mg m−3, μ=4.456 mm−1, T=100(2) K, 2θmax=136.3°, 7060 measured reflections, 1872 independent reflections (Rint=0.0399), 183 parameters refined, R=0.0541 (for 4205 reflections with I>2.00σ(I)), Rw=0.1523, max/min residual peaks in the final difference map 0.495/−0.817 e Å−3. CCDC 694293 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

    1. Pretsch EP, Seibl J, Clerc T, Simon W, editors. Tables of Spectral Data for Structure Determination of Organic Compounds. 2nd ed. Springer; Berlin: 1989.

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