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Abstract
Marine micro-organisms represent an under explored resource for the discovery of novel
antiviral agents. Here, we describe a series of peptides designated halovirs A-E (1-5)
that are produced during the saline fermentation of a marine-derived fungus of the
genus Scytalidium. These lipophilic, linear peptides are potent in vitro inhibitors
of the herpes simplex viruses 1 and 2. Evidence is presented that the halovirs directly
inactivate herpes viruses, a mechanism of action that could be applicable in the prevention
of HSV transmission. The total structures of these new compounds were established
by a combination of spectral and chemical techniques. Salient structural features
of the halovir hexapeptides include a nitrogen terminus acylated by myristic (C14)
or lauric (C12) acid, an unusual Aib-Hyp dipeptide segment, and a carboxyl terminus
reduced to a primary alcohol. A qualitative analysis of the secondary structures of
these molecules using variable temperature NMR experiments and NOE analyses is also
reported.