A convenient synthesis of cyclic peptides as regioselectively addressable functionalized templates (RAFT)

Chemoselectively addressable HCan building blocks in peptide synthesis:L-homocanaline derivatives

“…In order to evaluate the feasibility for the newly prepared Hcan derivatives in SPPS, we applied compounds 6 and 8 for the synthesis of chemoselectively addressable peptide templates. To this end, a cyclic peptide useful in TASP design [17] was prepared according to Scheme 2. The linear peptide 9 was built up in Sasrine 1 resin applying the standard protocols of Fmoc-based SPPS.…”

Molecular modeling and design of regioselectively addressable functionalized templates with rigidified three-dimensional structures

“…In order to bypass this well-known protein-folding problem, 5 some years ago we proposed the construction of non-native chain architectures with a high propensity for folding. 6,7 According to this concept, termed TASP (template-assembled synthetic proteins), topological templates 8,9 are used as a built-in device for directing covalently attached peptide blocks to a predetermined packing arrangement, resulting in branched chain architectures.…”

Amino Acid-Protecting Groups

“…147 It is useful as a temporary protecting group in the synthesis of cyclic and branched peptides. 148 ivDde is an improved derivative of Dde (1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-ethyl), 149,150,151 which is considerably less base-labile and therefore stable to Fmoc removal conditions and can be removed by hydrazinolysis. An additional advantage of ivDde is that its steric hindrance makes it is less prone to migrate to free Lys or Orn side chains ( Figure 6).…”