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J. Biol. Chem., Vol. 277, Issue 48, 45935-45941, November 29, 2002
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From the The enzymatic synthesis of the complete
L-alanyl1-L-alanine2
side chain of the peptidoglycan precursors of Enterococcus
faecalis was obtained in vitro using purified
enzymes. The pathway involved alanyl-tRNA synthetase and two ligases,
BppA1 and BppA2, that specifically transfer alanine from Ala-tRNA to
the first and second positions of the side chain, respectively. The
structure of the UDP-N-acetylmuramoyl-L-Ala-
Synthesis of the L-Alanyl-L-alanine
Cross-bridge of Enterococcus faecalis Peptidoglycan*
§,,,
,**
Laboratoire de Recherche Moléculaire
sur les Antibiotiques, Unité de Formation et de Recherche
Broussais-Hôtel Dieu, Université Paris VI-INSERM E0004, 15 rue de l'Ecole de Médecine, Paris 75270, cedex 06, France,
the § Institut de Biochimie, Biophysique Moléculaire
et Cellulaire, UMR 8619 CNRS, Université Paris-Sud, Orsay
91405, France, and the ¶ Wyeth Research, Pearl River, New York
10965
-D-Glu-L-Lys(N
-L-Ala1-L-Ala2)-D-Ala-D-Ala
product of BppA1 and BppA2 was confirmed by mass spectrometry (MS) and
MS/MS analyses. The peptidoglycan structure of the wild-type E. faecalis strain JH2-2 was determined by tandem reverse-phase
high-pressure liquid chromatography-MS revealing that most muropeptides
contained two L-alanyl residues in the cross-bridges and in
the free N-terminal ends. Deletion of the bppA2 gene was
associated with production of muropeptides containing a single alanyl
residue at these positions. The relative abundance of monomers, dimers,
trimers, and tetramers in the peptidoglycan of the bppA2
mutant indicated that precursors containing an incomplete side chain
were efficiently used by the DD-transpeptidases in the
cross-linking reaction. However, the bppA2 deletion
impaired expression of intrinsic 
-lactam resistance suggesting that
the low affinity penicillin-binding protein 5 did not function
optimally with precursors substituted by a single alanine.
*
This work was supported by Wyeth Research, by the Program de
Recherche Fondamentale en Microbiologie et Maladies Infectieuses et
Parasitaires (MENRT), and by the Fondation pour la Recherche Médicale.The costs of publication of this
article were defrayed in part by the
payment of page charges. The article
must therefore be hereby marked
"advertisement" in
accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
Present address: Idenix Pharmaceuticals, 125 Cambridge Park
Dr., Cambridge, MA 02140.
**
To whom correspondence should be addressed. Tel.: 33-1-43-25-00-33;
Fax: 33-1-43-25-68-12; E-mail: michel.arthur@bhdc.jussieu.fr.
Copyright © 2002 by The American Society for Biochemistry and Molecular Biology, Inc.
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