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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
Autoren
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.
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.
Publikationsverlauf
Artikel online veröffentlicht:
25. März 2025
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