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J Biol Chem, Vol. 273, Issue 35, 22773-22781, August 28, 1998
From Biochemie/Fachbereich Chemie, Philipps-Universität
Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany
Recently, considerable insight has been gained
into the modular organization and catalytic properties of nonribosomal
peptide synthetases. However, molecular and biochemical aspects of the condensation of two aminoacyl substrates or a peptidyl and an aminoacyl
substrate, leading to the formation of a peptide bond, have remained
essentially impenetrable. To investigate this crucial part of
nonribosomal peptide synthesis, an in vitro assay for a
dipeptide formation was developed. Two recombinant holomodules, GrsA
(PheATE), providing D-Phe, and a C-terminally truncated
TycB, corresponding to the first, L-Pro-incorporating
module (ProCAT), were investigated. Upon combination of the two
aminoacylated modules, a fast reaction is observed, due to the
formation of the linear dipeptide
D-Phe-L-Pro-S-enzyme on ProCAT, followed by a
noncatalyzed release of the dipeptide from the enzyme. The liberated
product was identified by TLC, high pressure liquid chromatography-mass spectrometry, 1H and 13C NMR, and comparison
with a chemically synthesized standard to be the expected
D-Phe-L-Pro diketopiperazine. Further
minimization of the two modules was not possible without a loss of
transfer activity. Likewise, a mutation in a proposed active-site motif (HHXXXDG) of the condensation domain giving ProCAT(H147V),
abolished the condensation reaction. These results strongly suggest the condensation domain to be involved in the catalysis of nonribosomal peptide bond formation with the histidine 147 playing a catalytic role.
Peptide Bond Formation in Nonribosomal Peptide Biosynthesis
CATALYTIC ROLE OF THE CONDENSATION DOMAIN
Copyright © 1998 by The American Society for Biochemistry and Molecular Biology, Inc.
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