[en] Various peptidoglycan fragments were synthesized from two anhydro-muramic acid derivatives protected with a Bn or a PMB group at the 4th position, in homogenate phase or on a solid support. In order to facilitate HPLC detection, a chromophoric group was attached to the peptide chain. The periplasmic amidase sAmiD of Escherichia coli was used to cleave the amide bond between the lactyl group of the MurNAc and the alpha-amino group of L-Ala where the peptide chain was at least a dipeptide (L-Ala-gamma-D-Glu) amidated by benzylamine on the gamma-carboxyl group of D-Glu. In the presence of a tripeptide chain (L-Ala-gamma-D-Glu-L-Lys) or a tetrapeptide chain (L-Ala-gamma-D-Glu-m-A(2)pm-D-Ala) higher hydrolysis rates were observed. We have also demonstrated that the presence of TNB on the epsilon-amino group of L-Lys only has a small influence on the hydrolysis capacity of sAmiD.
Research center :
GIGA CRC (Cyclotron Research Center) In vivo Imaging-Aging & Memory - ULiège CIP - Centre d'Ingénierie des Protéines - ULiège
Mercier, Frédéric ; Université de Liège - ULiège > Centre de recherches du cyclotron
Zervosen, Astrid ; Université de Liège - ULiège > Centre de recherches du cyclotron
Teller, Nathalie; Université de Liège - ULiège > Centre de recherche du Cyclotron
Frère, Jean-Marie ; Université de Liège - ULiège > Centre d'ingénierie des protéines
Herman, Raphaël ; Université de Liège - ULiège > Centre d'ingénierie des protéines
Pennartz, Anne; Université de Liège - ULiège > Centre d'ingénierie des protéines
Joris, Bernard ; Université de Liège - ULiège > Département des sciences de la vie > Physiologie et génétique bactériennes - Centre d'ingénierie des protéines
Luxen, André ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique de synthèse - Centre de recherches du cyclotron
Language :
English
Title :
1,6-AnhMurNAc derivatives for assay development of amidase AmiD.
Publication date :
2010
Journal title :
Bioorganic and Medicinal Chemistry
ISSN :
0968-0896
eISSN :
1464-3391
Publisher :
Elsevier Science, Oxford, United Kingdom
Volume :
18
Issue :
21
Pages :
7422-31
Peer reviewed :
Peer Reviewed verified by ORBi
Name of the research project :
Belgian Program on Interuniversity Poles of Attraction initiated by the Belgian state
Commentary :
Copyright (c) 2010 Elsevier Ltd. All rights reserved.
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