A versatileo-aminoanilide linker for native chemical ligation

Abstract

Chemical protein synthesis (CPS) is a consolidated field founded on the high chemospecificity of amide-forming reactions, most notably the native chemical ligation (NCL), but also on new technologies such as...

O-Aminoanilides in Protein Synthesis: N-Acylureas, Aryloxycarbonyl-o-Aminoanilides and Benzotriazoles

“…The interesting properties of Dbz-CONH2 and MeDbz-CONH2 peptides as surrogates of peptide-COSR via peptide-Nbz/MeNbz-CONH2 or peptide-Bt-CONH2 motivated the search for an o -aminoanilide surrogate that would combine the advantages of both and keep the robustness of MeDbz-CONH2 peptides. Thus, we found that 1,2-diaminobenzene linked to a PAL-resin can generate a peptide-Dbz (12) after TFA cleavage, or a peptide-(pCN-Phoc)Dbz (13) precursor of peptide-Nbz (Figure 4) [11]. The Dbz-PAL-resin is chemoselective, but it does not impair the acylation in the presence of strong electrophiles such as chloroformates.…”

Studies Towards the Chemical Synthesis of Sonic Hedgehog

“…This strategy fixed the issue, but it is only reactive through the Nbz (MeNbz) pathway. Most recently, we reported a linker based on 1,2-diaminobenzene which reacts through both pathways, avoids branching, and enables selenoester preparation through the benzotriazole pathway [6].…”

One-Step Synthesis of 3-(Fmoc-amino acid)-3,4-diaminobenzoic Acids

“…The use of a safety-catch resin is a feasible strategy for this purpose; in this approach, a given moiety is introduced in the cleavage step to the C-terminus of the product . Diaminobenzoate (Dbz) resin is an efficient safety-catch resin that is widely used to prepare thioesters. , Dbz resin was also used in the C-terminal functionalization of other peptides, including thiolactones, acylbenzimidazolinones, and cyclic peptides . Dbz resin has been used to prepare polymer–peptide conjugates and to introduce carboxaldehydes at the C-terminus …”

“… 3 Diaminobenzoate (Dbz) resin is an efficient safety-catch resin that is widely used to prepare thioesters. 4 , 5 Dbz resin was also used in the C-terminal functionalization of other peptides, including thiolactones, 6 acylbenzimidazolinones, 7 and cyclic peptides. 8 Dbz resin has been used to prepare polymer–peptide conjugates and to introduce carboxaldehydes at the C-terminus.…”