Pepticinnamins N, O, and P, Nonribosomal Peptides from the Soil-Derived Streptomyces mirabilis P8-A2

Cinnamoyl moiety containing nonribosomal peptides represented by pepticinnamin E are a growing family of natural products isolated from different Streptomyces species and possess diverse bioactivities. The soil bacterium Streptomyces mirabilis P8-A2 harbors a cryptic pepticinnamin biosynthetic gene...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2024-04, Vol.87 (4), p.1075-1083
Hauptverfasser:	Mohamed, Manar Magdy Mahmoud, Abboud, Maria Mahmoud, Maleckis, Matiss, Souza, Luciano D. O., Moreira, José M. A., Gotfredsen, Charlotte H., Weber, Tilmann, Ding, Ling
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Sprache:	eng
Schlagworte:	biosynthesis moieties multigene family nonribosomal peptides nuclear magnetic resonance spectroscopy prostatic neoplasms soil bacteria Streptomyces mirabilis
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container_title	Journal of natural products (Washington, D.C.)
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creator	Mohamed, Manar Magdy Mahmoud Abboud, Maria Mahmoud Maleckis, Matiss Souza, Luciano D. O. Moreira, José M. A. Gotfredsen, Charlotte H. Weber, Tilmann Ding, Ling
description	Cinnamoyl moiety containing nonribosomal peptides represented by pepticinnamin E are a growing family of natural products isolated from different Streptomyces species and possess diverse bioactivities. The soil bacterium Streptomyces mirabilis P8-A2 harbors a cryptic pepticinnamin biosynthetic gene cluster, producing azodyrecins as major products. Inactivation of the azodyrecin biosynthetic gene cluster by CRISPR-BEST base editing led to the activation and production of pepticinnamin E (1) and its analogues, pepticinnamins N, O, and P (2–4), the structures of which were determined by detailed NMR spectroscopy, HRMS data, and Marfey’s reactions. These new compounds did not show a growth inhibitory effect against the LNCaP and C4-2B prostate cancer lines, respectively.
doi_str_mv	10.1021/acs.jnatprod.4c00029
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subjects	biosynthesis moieties multigene family nonribosomal peptides nuclear magnetic resonance spectroscopy prostatic neoplasms soil bacteria Streptomyces mirabilis
title	Pepticinnamins N, O, and P, Nonribosomal Peptides from the Soil-Derived Streptomyces mirabilis P8-A2
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