A novel high-yield synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins: Important synthons for the synthesis of chromogenic/fluorogenic protease substrates
2011

New Method for Making Important Chemical Compounds

publication Evidence: high

Author Information

Author(s): Wu Xinghua, Chen Yu, Aloysius Herve, Hu Longqin, Trauner Dirk

Primary Institution: Department of Medicinal Chemistry, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey

Hypothesis

Can a new method improve the synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins?

Conclusion

The developed method allows for high-yield synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins.

Supporting Evidence

  • The method achieved excellent yields for various aminoacyl-pNAs and aminoacyl-AMCs.
  • Common protecting groups were well tolerated in the synthesis process.
  • The method was applicable under both aqueous and alcoholic conditions.

Takeaway

Scientists found a better way to make special chemical compounds that help in studying how enzymes work.

Methodology

The method involves the in situ formation of selenocarboxylate intermediates and subsequent amidation with azides.

Limitations

The method may not be applicable to all amino acids due to specific reactivity issues.

Digital Object Identifier (DOI)

10.3762/bjoc.7.117

Want to read the original?

Access the complete publication on the publisher's website

View Original Publication