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.
|Permanent link:||http://hdl.handle.net/10197/4988||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:||Anticapsin; Bacillus subtilis; Diketopiterazine||DOI:||10.1007/s00726-013-1571-4||Language:||en||Status of Item:||Peer reviewed|
|Appears in Collections:||Chemistry Research Collection|
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