Jiang Y,
Zhao J,
Hu L.
*
The State University of New Jersey, Piscataway, USA
2,2-Dimethyl-2-(
o-nitrophenyl)acetyl (DMNA) as an Assisted Cleavage Protecting Group for Amines.
Tetrahedron Lett. 2002;
43: 4589-4592
DOI:
10.1016/S0040-4039(02)00891-2
Key words
protecting groups - 2,2-dimethyl-2-(
o-nitrophenyl)acetyl group - hydrogenation
Significance
Protecting groups play an inherent role in organic synthesis. They are the backbone
for peptide drug discovery. Thus, chemists are always looking to develop new protecting
groups which can easily be installed and removed after the reaction. In 2002, the
authors developed a one-step protocol for the deprotection of 2,2-dimethyl-2-(o-nitrophenyl) acetyl (DMNA) group in amino acid derivatives and peptides.
Comment
Pd/C- or PtO2-catalyzed hydrogenation in presence of 10% AcOH is highly efficient for the deprotection
of 2,2-dimethyl-2-(o-nitrophenyl) acetyl (DMNA) group in amino acid derivatives and peptides. This protocol
is simple and mild. Other protecting groups are not affected under these reaction
conditions.
