Advertisement

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Biological Chemistry

Antibiotics From The Deep

January 28, 2008 | A version of this story appeared in Volume 86, Issue 4

Structure of marinopyrrole

A veritable treasure trove of medicinally relevant compounds has once again been found by plumbing the oceans' depths. William Fenical and coworkers at Scripps Institution of Oceanography have identified an unusual pair of antibiotics isolated from bacteria that inhabit ocean sediments. The compounds, dubbed marinopyrrole A (shown) and B, possess an N,C2-linked bispyrrole motif that's never been observed in natural products (Org. Lett., DOI: 10.1021/ol702952n). Postdoc Chambers C. Hughes isolated the chiral molecules as single atropo-enantiomers, suggesting that their biosynthesis involves a critical enzyme-mediated pyrrole coupling. Fenical and his team were able to isomerize marinopyrrole A to its nonnatural atropo-enantiomer by heating it. This enantiomer, along with the natural marinopyrroles, exhibits promising antimicrobial activity against methicillin-resistant Staphylococcus aureus. By focusing a synthetic effort on the marinopyrroles' novel bispyrrole structure, Fenical says, chemists might discover new compounds for fighting drug-resistant infections.

Article:

This article has been sent to the following recipient:

0 /1 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.