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Synfacts 2025; 21(04): 440
DOI: 10.1055/a-2539-2507
DOI: 10.1055/a-2539-2507
Peptide Chemistry
Chemoselective Deprotection of Fmoc and OMe in N-Fmoc-Amino Acid and N-Fmoc-Dipeptide Methyl Esters
Di Gioia ML,
Leggio A,
Le Pera A,
Liguori A,
Perri F,
Siciliano C.
Università degli Studi della Calabria, Arcavàcata, Italy
Alternative and Chemoselective Deprotection of the α-Amino and Carboxy Functions of N-Fmoc-Amino Acid and N-Fmoc-Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl3/N,N-Dimethylaniline Reagent System.
Eur. J. Org. Chem. 2004; 4437-4441
DOI: 10.1002/ejoc.200400321
Alternative and Chemoselective Deprotection of the α-Amino and Carboxy Functions of N-Fmoc-Amino Acid and N-Fmoc-Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl3/N,N-Dimethylaniline Reagent System.
Eur. J. Org. Chem. 2004; 4437-4441
DOI: 10.1002/ejoc.200400321
Keywords
chemoselective deprotection - AlCl3 - N,N-dimethylaniline - Fmoc-deprotection - methyl ester hydrolysis
Significance
Development of simple, straightforward methods for selective deprotection of protecting groups is key for successful peptide synthesis. In 2004, the authors developed chemoselective removal of the N-Fmoc or -OMe group from the N-Fmoc-α-amino acid and peptide methyl esters by modulating the molar ratio of the AlCl3 and N,N-dimethylaniline.
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Comment
The reactions proceeded smoothly and delivered the corresponding desired products in good yields. This chemoselective deprotection method was also applied to N-Fmoc-dipeptide methyl esters.
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Publication History
Article published online:
25 March 2025
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