Effect of capping groups at the N- and C-termini on the conformational preference of α,β-peptoids

Abstract

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Cyclic α,β-Tetrapeptoids: Sequence-Dependent Cyclization and Conformational Preference

“…The efficient cyclization of a tetramer bearing propargyl side chains gave rise to a 16-membered ring that adopted an all- cis arrangement in the crystal structure. Recently, we have introduced a novel peptoid backbone composed of α- and β-peptoid monomers in alternation . Employing HATU-optimized conditions, we successfully prepared a cyclic α,β-tetrapeptoid carrying benzyloxyethyl side chains on the α-residues and ( S )-1-phenylethyl side chains ( spe ) on the β-residues in 82% yield for the macrocyclization .…”

Chiral Display of Pyrenes on a Peptoid Backbone: Conformational Homogeneity of Peptoid Controls Excimer Chirality

“…[9,10,20] Peptoids were synthesized with and without an N-acetyl group to investigate the influence of N-terminal capping on the conformational homogeneity of the secondary structure (Figure 1B). [37] The synthesis began with a substitution reaction between tert-butyl bromoacetate and s1pye to yield monomer 1. The peptoids were then elongated by repeating a reaction cycle comprising acylation with bromoacetyl bromide followed by displacement with s1pye.…”

Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study

“…To a solution of the linear α,β-hexapeptoid 12 (427 mg, 0.40 mmol, 1.0 equiv.) in CH 2 Cl 2 (0.10 M) at rt under Ar was added TFA (1 mL per 1 mL CH 2 Cl 2 ) and the resulting mixture was stirred for 2 h at rt.…”

“…8 Briefly, the linear precursor was composed of (S)-N-(1-phenylethyl)glycine and (S)-N-(1-phenylethyl)-β-alanine monomers in alternation and was synthesised by a solution-phase submonomer approach. 12 The C-terminal tBu-capping group of the synthesised linear peptoid was cleaved using trifluoroacetic acid and subsequent HATU-mediated cyclisation led to cP1 in 64% yield (see ESI † for details).…”