Repository logo
  • Log In
    New user? Click here to register.Have you forgotten your password?
University College Dublin
    Colleges & Schools
    Statistics
    All of DSpace
  • Log In
    New user? Click here to register.Have you forgotten your password?
  1. Home
  2. College of Science
  3. School of Chemistry
  4. Chemistry Research Collection
  5. The synthesis and biological testing of bacilysin analogues
 
  • Details
Options

The synthesis and biological testing of bacilysin analogues

Author(s)
Robertson, Keith  
Murphy, Cormac D.  
Paradisi, Francesca  
Uri
http://hdl.handle.net/10197/4988
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
Subjects

Anticapsin

Bacillus subtilis

Diketopiterazine

DOI
10.1007/s00726-013-1571-4
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
https://creativecommons.org/licenses/by-nc-nd/3.0/ie/
File(s)
No Thumbnail Available
Name

Robertson_Amino_Acids_2013.doc

Size

949 KB

Format

Microsoft Word

Checksum (MD5)

07acc46f0721f23565faac1660cf0245

Owning collection
Chemistry Research Collection

Item descriptive metadata is released under a CC-0 (public domain) license: https://creativecommons.org/public-domain/cc0/.
All other content is subject to copyright.

For all queries please contact research.repository@ucd.ie.

Built with DSpace-CRIS software - Extension maintained and optimized by 4Science

  • Cookie settings
  • Privacy policy
  • End User Agreement