Size-dependent cation transport by cyclic α-peptoid ion carriers

Cola, Chiara De; Licen, Sabina; Comegna, Daniela; Cafaro, Emiddio; Bifulco, Giuseppe; Izzo, Irene; Tecilla, Paolo; Riccardis, Francesco De

doi:10.1039/b905665c

Cited by 63 publications

(45 citation statements)

References 23 publications

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“…cyclo-(Nspe-Nspe-Nph) 2 (9) 2 7 cctcct cyclo-(Nme) 6 (10) 1 5 cctcct cyclo-(Npm 2 -Nph-Npm 2 -Nnp) (11) 2 8 all-trans cyclo-(Nme) 6 Na complex (10˙Na + ) 1 5 all-trans cyclo-(Nbe) 6 …”

Section: Resultsmentioning

confidence: 99%

“…32 and 33). Coloured side-chains highlight the macrocycle pre-organization; c) crystal packing of cyclo-(NMe) 6 and d) of the corresponding Na + complex as viewed along the a axis. Side by side intertubular contacts are provided by cis carbonyl groups, which Fig.…”

Section: Heptameric Cyclic Peptoidsmentioning

confidence: 99%

“…This is determined mainly by hydrogen bonds involving two trans carbonyl groups and two water molecules, which are located respectively above and below the plane formed by the peptoid backbone. PF 6 − anions occupy interstitial spaces. 28 a) Columnar arrangement of molecules in the cyclo-(Nme) 6 (10) free form and b) as a sodium complex (10·Na + ) to form a 1D coordination polymer.…”

Section: Heptameric Cyclic Peptoidsmentioning

confidence: 99%

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Solid state assembly of cyclic α-peptoids

et al. 2014

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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. CrystEngComm, 2014, 16, 3667-3687 | 3667 This journal is a Hydrate form. b Methanol solvate. c Both anhydrous and hydrate form. d Ethanol solvate. e List of abbreviations: Sar = sarcosine, Nal = N-(allyl)glycine, Nnp = N-(naphthyl)glycine, Nbe = N-(benzyloxyethyl)glycine, Npm = N-(benzyl)glycine, Nme = N-(methoxyethyl)glycine, Nph = N-(phenyl)glycine, Npa = N-(propargyl)glycine, Nspe = (S)-N-(1-phenylethyl)glycine. CrystEngComm Highlight

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“…cyclo-(Nspe-Nspe-Nph) 2 (9) 2 7 cctcct cyclo-(Nme) 6 (10) 1 5 cctcct cyclo-(Npm 2 -Nph-Npm 2 -Nnp) (11) 2 8 all-trans cyclo-(Nme) 6 Na complex (10˙Na + ) 1 5 all-trans cyclo-(Nbe) 6 …”

Section: Resultsmentioning

confidence: 99%

Section: Heptameric Cyclic Peptoidsmentioning

confidence: 99%

Section: Heptameric Cyclic Peptoidsmentioning

confidence: 99%

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Solid state assembly of cyclic α-peptoids

et al. 2014

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“…Moreover, in a follow-up study, these groups reported cation transport carried by cyclic peptoids across a phospholipid membrane. [52] Two additional cyclic peptoids, an octamer and a decamer, were synthesized and characterized, and their size-dependent selectivity for first group alkali metal cation transport was demonstrated.…”

Section: Metal Coordination In Peptidomimetic Foldamersmentioning

confidence: 99%

Conformational Control in Metallofoldamers: Design, Synthesis and Structural Properties

Maayan

2009

Eur J Org Chem

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Metallofoldamers are sequence‐specific oligomers, which are designed to fold into three‐dimensional architectures upon metal coordination. Their folding can involve additional noncovalent interactions and results in new chiral secondary structures, enhanced stabilization of existing secondary structures, or unique materials for specific applications. This microreview highlights recent advances in the field.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…This conjugate was shown to bind the same monoclonal antibodies as HNE itself and therefore may be of use as a new measles vaccine. The development of a novel approach to macrocyclic peptoids for use as ionophores has been reported (De Cola et al, 2009). Cyclotides, disulfide rich cyclic peptides, have been isolated for the first time from the Melicytus family of plants (Trabi et al, 2009).…”

Section: The Chemical Biology Of Proteinsmentioning

confidence: 99%