Conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction

Abstract

Synthesis and the structural analysis of conformationally stable peptide macrocycles assembled using the Petasis borono-Mannich reaction are reported.

Submonomer synthesis of peptoids containing trans-inducing N-imino- and N-alkylamino-glycines

“…S27 †). 22 Because most peptoid monomers lack hydrogen bond donors, these N-alkylamino glycine monomers should exhibit unique properties that could be complementary to N-alkoxy glycines 8 as hydrogen-bond acceptors. Notably, this trans-inducing monomer pair differ by a single nitrogen to oxygen atom substitution, which may promote productive side chain packing interactions.…”

Diversity-oriented synthesis of peptide-boronic acids by a versatile building-block approach

“…Due to the non-acidic cleavage conditions, the described method provides access to synthetic intermediates readily applicable to late-stage diversications, e.g. petasis reactions [41][42][43] or cross-coupling reactions. 44,45 Final compounds were obtained by side-chain deprotection using TFA-based cleavage solutions and subsequent HPLC purication.…”

Grafting Bis(heteroaryl) Motifs into Ring Structures

“…Hydrogen bonds originating from the phenylalanine and alanine residues in both molecules are maintained, however the N τ ‐cyclo‐GFGAH exhibits a potential hydrogen bond with the pyrazole N–H. Furthermore, the macrocycle 7g also contains a hydrogen‐bonded exo ‐amide and its role as a conformational control element has been observed and recognized in several other systems , …”