Protection of carboxamide functions by the trityl residue. Application to peptide synthesis

DOI: 10.1016/S0040-4039(00)74872-6

Source and publish data:

Tetrahedron Letters p. 739 - 742 (1991)

Update date:2022-07-29

Topics:

Authors:

Sieber Sieber

Riniker Riniker

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Article abstract of DOI:10.1016/S0040-4039(00)74872-6

Carboxamide functions may be tritylated by an acid-catalyzed reaction with triphenylmethanol and acetic anhydride in glacial acetic acid. The ω-trityl group of asparagine and glutamine is cleavable by TFA, but stable to strong mineral acids in aqueous solution, as well as to nucleophiles and bases. In peptide syntheses, it is ideally suited for combination with side-chain protections of the t.butyl-type.

Full text of DOI:10.1016/S0040-4039(00)74872-6

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