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. 2012 Apr 27;75(4):644-9.
doi: 10.1021/np200886x. Epub 2012 Mar 22.

Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp

Zhenjian Lin  1 , Malem Flores, Imelda Forteza, Niel M Henriksen, Gisela P Concepcion, Gary Rosenberg, Margo G Haygood, Baldomero M Olivera, Alan R Light, Thomas E Cheatham 3rd, Eric W Schmidt
Affiliations

Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp

Zhenjian Lin et al. J Nat Prod. .

Abstract

Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.

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Figures

Figure 1
Figure 1
Selected 1H-1H COSY, HMBC and NOESY correlations for 1.
Figure 2
Figure 2
Molecular modeling of FDLA derivatives of Phg, DHPhg, and ClPhg with lowest quantum mechanical energy.
Figure 3
Figure 3
Key NOESY correlations and rotational model for the polyketide unit in totopotensamide A (1).
See this image and copyright information in PMC

References

    1. Gil-Turnes MS, Hay ME, Fenical W. Science. 1989;4926:116–118. - PubMed
    1. Jensen PR, Fenical W. Ann Rev Microbiol. 1994;48:559–584. - PubMed
    1. Piel J. Nat Prod Rep. 2009;26:338–362. - PubMed
    1. Lin Z, Reilly CA, Antemano R, Hughen RW, Marett L, Concepcion GP, Haygood MG, Olivera BM, Light A, Schmidt EW. J Med Chem. 2011;54:3746–3755. - PMC - PubMed
    1. Lin Z, Antemano RR, Hughen RW, Tianero MDB, Peraud O, Haygood MG, Concepcion GP, Olivera BM, Light A, Schmidt EW. J Nat Prod. 2010;73:1922–1926. - PMC - PubMed

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