Furan and Lactam Jadomycin Biosynthetic Congeners Isolated from Streptomyces venezuelae ISP5230 Cultured with Nε-Trifluoroacetyl-l-lysine

Journal of Natural Products
Stephanie M ForgetDavid L Jakeman

Abstract

Angucycline antibiotics are composed of a classical four-ring angularly linked polyaromatic backbone. Differential cyclization chemistry of the A- and B-rings in jadomycin biosynthesis led to the discovery of two new furan analogues, while oxidation led to a ring-opened form of the jadomycin Nε-trifluoroacetyl-l-lysine (TFAL) congener. The compounds were isolated from Streptomyces venezuelae ISP5230 cultures grown with TFAL. Biosynthetic incorporation using d-[1-(13)C]-glucose in cultures enabled the unambiguous assignment of the aldehyde, alcohol, and amide functionalities present in these new congeners through NMR spectroscopy. Tandem mass spectrometry analysis of cultures grown with (15)Nα- or (15)Nε-lysine demonstrated the incorporation of Nα exclusively into the angucycline backbone, contrasting results with ornithine [J. Am. Chem. Soc. 2015, 137, 3271]. Compounds were evaluated against antimicrobial and cancer cell panels and found to possess good activity against Gram-positive bacteria.

References

Apr 9, 2004·Journal of the American Chemical Society·Uwe RixJürgen Rohr
Feb 17, 2005·Bioorganic & Medicinal Chemistry Letters·David L JakemanShannon C Timmons
Mar 19, 2005·Chembiochem : a European Journal of Chemical Biology·Uwe RixJürgen Rohr
Oct 28, 2005·Journal of Applied Toxicology : JAT·Nikolay V GoncharovAndrey S Radilov
Mar 29, 2006·Journal of Industrial Microbiology & Biotechnology·David L JakemanLeo C Vining
Feb 3, 2007·Natural Product Reports·Christian HertweckAndreas Bechthold
Jun 16, 2007·Chembiochem : a European Journal of Chemical Biology·Charles N BorissowDavid L Jakeman
Dec 17, 2008·Antimicrobial Agents and Chemotherapy·David L JakemanSusan E Douglas
Dec 22, 2011·Natural Product Reports·Madan K KharelJürgen Rohr
Apr 3, 2012·Current Opinion in Chemical Biology·Madan K Kharel, Jürgen Rohr
Apr 19, 2012·The Journal of Antibiotics·János Bérdy
Oct 30, 2012·Journal of the American Chemical Society·Nidhi TibrewalJürgen Rohr
Jul 23, 2014·ACS Medicinal Chemistry Letters·Vinayak S KhodadeHarinath Chakrapani
Sep 11, 2014·Natural Product Reports·Mark S ButlerMatthew A Cooper
Feb 19, 2015·Journal of the American Chemical Society·Andrew W RobertsonDavid L Jakeman
Jun 3, 2015·Journal of Natural Products·Camilo F Martinez-FarinaDavid L Jakeman
Jul 24, 2015·Journal of Natural Products·Andrew W RobertsonDavid L Jakeman
Aug 20, 2015·Chemical Communications : Chem Comm·Camilo F Martinez-Farina, David L Jakeman
Oct 27, 2015·Proceedings of the National Academy of Sciences of the United States of America·Maureen E HillenmeyerLouise K Charkoudian
Jun 9, 2016·Trends in Pharmacological Sciences·Mark G Moloney

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