The Nw-phospho-l-arginine energy-buffering system is mainly
present in invertebrates for regulating energy requirements
when it is highly needed, such as in the flight muscles of an
insect or when energy supply fluctuates, as in the medically
important protozoa Trypanosoma brucei, Trypanosoma cruzi,
and Leishmania major. The lack of availability of this important
metabolite was due to a tedious chemical procedure, by which
Nw-phospho-l-arginine was prepared in over 5 reaction steps
in a low yield. Therefore, we aimed at improving the synthetic
methodology for the preparation of this important metabolite.
As site- and enantioselective kinases have been very useful catalysts
for biocatalytic phosphorylations in s... More
The Nw-phospho-l-arginine energy-buffering system is mainly
present in invertebrates for regulating energy requirements
when it is highly needed, such as in the flight muscles of an
insect or when energy supply fluctuates, as in the medically
important protozoa Trypanosoma brucei, Trypanosoma cruzi,
and Leishmania major. The lack of availability of this important
metabolite was due to a tedious chemical procedure, by which
Nw-phospho-l-arginine was prepared in over 5 reaction steps
in a low yield. Therefore, we aimed at improving the synthetic
methodology for the preparation of this important metabolite.
As site- and enantioselective kinases have been very useful catalysts
for biocatalytic phosphorylations in straightforward syntheses
of phosphorylated metabolites, a stable and selective
arginine kinase has been selected for the selective phosphorylation
of l-arginine. The Arg gene has been cloned and expressed
in E. coli and a highly active arginine kinase has been
prepared. A simple synthesis of Nw-phospho-l-arginine has
been developed by arginine kinase catalyzed phosphorylation
of l-arginine combined with the recycling of the phosphorylating
agent ATP by using the phosphoenolpyruvate/pyruvate
kinase system. After standard work-up, the desired product Nwphospho-l-arginine
was obtained in gram quantities and in
one step.