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  • Title: Eight-membered ring-containing jadomycins: implications for non-enzymatic natural products biosynthesis.
    Author: Robertson AW, Martinez-Farina CF, Smithen DA, Yin H, Monro S, Thompson A, McFarland SA, Syvitski RT, Jakeman DL.
    Journal: J Am Chem Soc; 2015 Mar 11; 137(9):3271-5. PubMed ID: 25692677.
    Abstract:
    Jadomycin Oct (1) was isolated from Streptomyces venezuelae ISP5230 and characterized as a structurally unique eight-membered l-ornithine ring-containing jadomycin. The structure was elucidated through the semisynthetic derivatization of starting material via chemoselective acylation of the l-ornithine α-amino group using activated succinimidyl esters. Incorporation of 5-aminovaleric acid led to jadomycin AVA, a second eight-membered ring-containing jadomycin. These natural products illustrate the structural diversity permissible from a non-enzymatic step within a biosynthetic pathway and exemplifies the potential for discovery of novel scaffolds.
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