1583306-65-3Relevant articles and documents
Small head-to-tail macrocyclic α-peptoids
Culf, Adrian S.,?uperlovi?-Culf, Miroslava,Léger, Daniel A.,Decken, Andreas
, p. 2780 - 2783 (2014)
A convenient and efficient methodology for the head-to-tail macrocyclization of small 3-mer, 4-mer, and 5-mer α-peptoid acids (9-, 12-, and 15-atom N-substituted glycine oligomers) is described. The cyclic trimer has a ccc amide sequence in the crystal structure, whereas the tetramer has ctct and the pentamer has ttccc stereochemistry. NMR analysis reveals rigid structures in solution. These synthetic macrocycles may prove useful in medicinal and materials applications.
From Cyclic Peptoids to Peraza-macrocycles: A General Reductive Approach
Schettini, Rosaria,D'Amato, Assunta,Pierri, Giovanni,Tedesco, Consiglia,Della Sala, Giorgio,Motta, Oriana,Izzo, Irene,De Riccardis, Francesco
, p. 7365 - 7369 (2019/10/02)
Peraza-macrocycles form chelates of high thermodynamic and kinetic stability useful in diagnostic imaging (MRI, SPECT, PET), in coordination chemistry, and as catalysts. In this letter, we report an advantageous method to prepare these compounds via BHsu
Conformational isomerism in cyclic peptoids and its specification
D'Amato,Schettini,Della Sala,Costabile,Tedesco,Izzo,De Riccardis
, p. 9932 - 9942 (2017/12/05)
Most of the structural studies made on the secondary structure of peptoids describe their geometric attributes in terms of the classic Ramachandran plot (based on the local analysis of ω, ψ, χ, φ dihedral angles). However, little intuitive understanding is available from internal coordinates when stereochemistry is involved. In this contribution we list all the conformationally stable cyclic peptoids reported up to the year 2017 and propose a simple method to define their geometric arrangement in terms of planar chirality. Evidence of conformational isomerism (due to the long average time of single bond rotation) and conformational chirality (induced by the absence of roto-reflection axes) in this promising class of synthetic macrocycles is provided by NMR spectroscopy (using Pirkle's alcohol as chiral solvating agent) and careful evaluation of X-ray crystallographic studies. The full understanding of the oligomeric macrocycles' structural properties and the clear framing of their conformational isomerism in a proper conceptual scheme is fundamental for future application of peptoids in asymmetric synthesis, chiral recognition and supramolecular chemistry.
Solid state assembly of cyclic α-peptoids
Tedesco, Consiglia,Erra, Loredana,Izzo, Irene,De Riccardis, Francesco
, p. 3667 - 3687 (2014/05/06)
The solid state assembly of free and metal coordinated cyclic α-peptoids has been examined with the aim to find common underlying features and to direct the design of new functional biomimetic materials with desired properties in terms of molecular recognition, drug delivery and catalysis. The lack of the amide proton prevents the formation of NH...OC hydrogen bonds and weaker interactions play a key role in the intermolecular recognition and assembly. Inter-annular CH...OC hydrogen bonds provide face to face or side by side arrangement of macrocycles in a way that can be considered the peptoid counterpart of β-sheet secondary structure in proteins. The choice of side chains is crucial for the solid state properties of α-cyclic peptoids. Side chains have a strong influence on the solid state assembly of peptoid macrocycles: they may provide competing interactions to CH...OC inter-annular hydrogen bonds, leading either to a T-shape or to a tubular arrangement of the peptoid macrocycles. The size of the macrocycle is another important factor influencing the tubular arrangement. In particular, a larger size of the macrocycle promotes side by side with respect to T-shape interactions. Hirshfeld surfaces and their fingerprint analysis allowed the analysis of the contributions of weak intermolecular interactions, such as weak CH...OC hydrogen bonds and CH-pi interactions, towards the crystal packing. This journal is the Partner Organisations 2014.
