Biologically Inspired Total Synthesis of Ulbactin F, an Iron-Binding Natural Product.
Shapiro JA1, Morrison KR1, Chodisetty SS1, Musaev DG2, Wuest WM1,3.
Org Lett. 2018 Sep 10. doi: 10.1021/acs.orglett.8b02599
Abstract
Natural products from environmental microbiomes provide exquisite templates for elucidating biological activity in the search for new drugs. A recently discovered marine Brevibacillus sp. metabolite, ulbactin F, was found to inhibit tumor cell migration
and invasion at IC50 < 3 μM. Herein, we disclose the first total synthesis of ulbactin F and epi-ulbactin F, which was modeled after the biosynthetic pathway. The scaffold bears structural similarity to siderophores of human pathogens but contains a
novel tricyclic ring system derived from cysteine. We have found that ulbactin F forms low-affinity metal complexes, with a preference for Fe3+ and Cu2+, which may hint both at its environmental role and its antimetastatic mechanism of action.
PMID: 30199265 DOI: 10.1021/acs.orglett.8b02599
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