The concept of internal solubilization in peptide synthesis: ethylene glycol-based protecting groups

Recent trends in Cys- and Ser/Thr-based synthetic strategies for the elaboration of peptide constructs

“…Other techniques were also reported for the synthesis of difficult sequences, including the substitution of the amide proton with a reversible protecting group (pseudo-prolines, 167 Hmb 168 or Dmb 169 ) or with protecting groups inducing internal solubilization. 170 Nevertheless, the (O)-and (S)-acyl isopeptide methods have the major advantages of (i) utilizing conventional amino acid and (ii) providing an isomer of the native peptide bond which can be isomerized under a variety of controlled conditions (Fig. 23b).…”

Amino Acid-Protecting Groups

“…235 -4-(3,6,9-trioxadecyl)oxybenzyl (TEGBz or TEGBn). 236 It is a recently developed protecting group which is removed with TFA-DCM. It has been used for the solid phase synthesis of "difficult" peptide sequences (those very prone to aggregate) because it minimizes chain aggregation during the synthesis.…”

Synthesis of small protein domains by automated flow chemistry

“…36,37 The use of chaotropic solvents, polyethylene type sidechain protecting groups, pseudoproline derivatives, depsipeptides and N-alkyl amino acids were shown to improve synthetic results. [38][39][40][41][42][43][44][45][46][47] As residues are coupled step by step, the properties of the polymer matrix also change, creating the need for residence time control (Fig. S3 †).…”