Issue 4, 2008
From the journal:

Organic & Biomolecular Chemistry

Synthesis and testing of chromogenic phenoxazinone substrates for β-alanyl aminopeptidase†

Andrey V. Zaytsev,a   Rosaleen J. Anderson,*a   Alexandre Bedernjak,a   Paul W. Groundwater,*a   Yongxue Huang,a   John D. Perry,b   Sylvain Orenga,c   Celine Roger-Dalbertc  and  Arthur Jamesd  

* Corresponding authors

a Pharmacy, Chemistry and Biomedical Sciences, University of Sunderland, Sunderland, U.K.
E-mail: paul.groundwater@sunderland.ac.uk
Fax: +44(0)191 515 3405
Tel: +44(0)191 515 2600

b Department of Microbiology, Freeman Hospital, Newcastle upon Tyne
E-mail: john.perry@nuth.northy.nhs.uk
Fax: +44(0)191 223 1224
Tel: +44(0)191 284 3111 × 26691

c R & D Microbiology, bioMerieux, 3 Route del Port Michaud, 28 390 La Balme-les-Grottes, France
E-mail: sylvain.orenga@eu.biomerieux.com
Fax: +33 (0)474 952 632
Tel: +33 (0)474 952 543

d School of Applied Sciences, Ellison Place, Northumbria University, Newcastle upon Tyne, U.K.

Abstract

Novel 7-N-(β-alanyl)aminophenoxazin-3-one salts 27a–d have been synthesized and tested as chromogenic substrates for β-alanyl aminopeptidase, which is present in Pseudomonas aeruginosa, the most common respiratory pathogen in patients with cystic fibrosis. The biological results show that 7-N-(β-alanyl)amino-1-pentylphenoxazin-3-one trifluoroacetate salt27a is a chromogenic substrate for this bacterium, with a low degree of diffusion in nutrient media for growing bacterial cultures and a bright red colour, making it easily distinguishable from the agar background.

Graphical abstract: Synthesis and testing of chromogenic phenoxazinone substrates for β-alanyl aminopeptidase

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Article information

DOI
https://doi.org/10.1039/B716978G
Article type
Paper
Submitted
02 Nov 2007
Accepted
06 Dec 2007
First published
04 Jan 2008

Org. Biomol. Chem., 2008,6, 682-692

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Synthesis and testing of chromogenic phenoxazinone substrates for β-alanyl aminopeptidase

A. V. Zaytsev, R. J. Anderson, A. Bedernjak, P. W. Groundwater, Y. Huang, J. D. Perry, S. Orenga, C. Roger-Dalbert and A. James, Org. Biomol. Chem., 2008, 6, 682 DOI: 10.1039/B716978G

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