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The synthesis and biological testing of bacilysin analogues
Date Issued
2013-11
Date Available
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
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
File(s)
No Thumbnail Available
Name
Robertson_Amino_Acids_2013.doc
Size
949 KB
Format
Microsoft Word
Checksum (MD5)
07acc46f0721f23565faac1660cf0245
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