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Publication year - 2021
Publication title -
peptide science
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.533
H-Index - 7
ISSN - 2475-8817
DOI - 10.1002/pep2.24232
Subject(s) - chemistry , thioester , amine gas treating , benzotriazole , peptide , stereochemistry , glycine , combinatorial chemistry , thiol , amino acid , organic chemistry , biochemistry , enzyme
Ferrer‐Gago & Koh report a method for the synthesis of complex proteins by native chemical ligation (NCL). The attachment of o ‐phenylenediamine (PheDA), with and without an electron withdrawing group, to a chlorotrityl chloride resin converts one amino group of PheDA to a secondary amine. This changes the reactivity of the two amino groups, enabling synthesis of o ‐aminoanilide peptides without overacylation of the additional unprotected amino group. PheDA attached to the trityl resin allows the incorporation of glycine in only one amino group, facilitating the synthesis of C‐terminal glycine‐rich o ‐aminoanilide peptides. After treatment with sodium nitrite, these form acyl‐benzotriazole active esters. The esters undergo a thiol exchange yielding thioester peptides used in NCL reactions. (doi: 10.1002/pep2.24194 )