The synthesis and biological testing of bacilysin analogues

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Title: The synthesis and biological testing of bacilysin analogues
Authors: Robertson, Keith
Murphy, Cormac D.
Paradisi, Francesca
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Date: Nov-2013
Online since: 2014-11-01T04:00:11Z
Abstract: A series of compounds based on the structure of bacilysin were synthesised and tested for antibacterial activity. The key steps in the syntheses are the coupling of an iodide to a diketopiperazine (DKP) and mono-lactim ether scaffold, respectively. The diastereoselectivity of the coupling reactions was dependant on the scaffold, with selectivity for DKP of about 4:1 and mono-lactim ether exceeding 98:2. Subsequent elaboration of the compounds to give open chain dipeptides and DKPs that mimic the structure of bacilysin but substitute the epoxy ketone for a saturated or unsaturated ketone is described. Overall yield from coupling to final product was between 5 and 21 %, with the yield of the saturated products notably higher. The open chain dipeptides demonstrated moderate antibacterial and antifungal activity.
Type of material: Journal Article
Publisher: Springer
Journal: Amino Acids
Volume: 45
Issue: 5
Start page: 1157
End page: 1168
Copyright (published version): 2013, Springer Vienna
Keywords: AnticapsinBacillus subtilisDiketopiterazine
DOI: 10.1007/s00726-013-1571-4
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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