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Synfacts 2023; 19(05): 0529
DOI: 10.1055/s-0042-1752480
Peptide Chemistry

Deprotection of 2,2-Dimethyl-2-(o-nitrophenyl)acetyl (DMNA) Group in Amino Acids and Peptides

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
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.
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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.


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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.


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Publication History

Article published online:
14 April 2023

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