Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer

A spectroscopic and computational study

E. De Santis, Alison A. Edwards, Bruce David Alexander, S. J. Holder, A.-S. Biesse-Martin, B. V. Nielsen, Dharmit Mistry, L. Waters, G. Siligardi, Rabia Hussain, S. Faure, C. Taillefumier

Research output: Contribution to journalArticle

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Abstract

We describe the qualitative and quantitative analysis of the complexation properties towards cations of a cyclic peptoid hexamer composed of alternating α- and β-peptoid monomers, which bear exclusively chiral (S)-phenylethyl side chains (spe) that have no noticeable chelating properties. The binding of a series of monovalent and divalent cations was assessed by 1H NMR, circular dichroism, fluorescence and molecular modelling. In contrast to previous studies on cations binding by 18-membered α-cyclopeptoid hexamers, the 21-membered cyclopeptoid cP1 did not complex monovalent cations (Na+, K+, Ag+) but showed selectivity for divalent cations (Ca2+, Ba2+, Sr2+ and Mg2+). Hexacoordinated C-3 symmetrical complexes were demonstrated for divalent cations with ionic radii around 1 Å (Ca2+ and Ba2+), while 5-coordination is preferred for divalent cations with larger (Ba2+) or smaller ionic radii (Mg2+).
Original languageEnglish
Pages (from-to)11371-11380
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number48
Early online date2 Nov 2016
DOIs
Publication statusPublished - 2016

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Peptoids
Divalent Cations
Complexation
cations
Monovalent Cations
Cations
Molecular modeling
Circular Dichroism
Chelation
Monomers
Fluorescence
Nuclear magnetic resonance
radii
qualitative analysis
bears
quantitative analysis
dichroism
Chemical analysis
monomers
selectivity

Cite this

De Santis, E., Edwards, A. A., Alexander, B. D., Holder, S. J., Biesse-Martin, A-S., Nielsen, B. V., ... Taillefumier, C. (2016). Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: A spectroscopic and computational study. Organic and Biomolecular Chemistry, 14(48), 11371-11380. https://doi.org/10.1039/C6OB01954D
De Santis, E. ; Edwards, Alison A. ; Alexander, Bruce David ; Holder, S. J. ; Biesse-Martin, A.-S. ; Nielsen, B. V. ; Mistry, Dharmit ; Waters, L. ; Siligardi, G. ; Hussain, Rabia ; Faure, S. ; Taillefumier, C. / Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer : A spectroscopic and computational study. In: Organic and Biomolecular Chemistry. 2016 ; Vol. 14, No. 48. pp. 11371-11380.
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abstract = "We describe the qualitative and quantitative analysis of the complexation properties towards cations of a cyclic peptoid hexamer composed of alternating α- and β-peptoid monomers, which bear exclusively chiral (S)-phenylethyl side chains (spe) that have no noticeable chelating properties. The binding of a series of monovalent and divalent cations was assessed by 1H NMR, circular dichroism, fluorescence and molecular modelling. In contrast to previous studies on cations binding by 18-membered α-cyclopeptoid hexamers, the 21-membered cyclopeptoid cP1 did not complex monovalent cations (Na+, K+, Ag+) but showed selectivity for divalent cations (Ca2+, Ba2+, Sr2+ and Mg2+). Hexacoordinated C-3 symmetrical complexes were demonstrated for divalent cations with ionic radii around 1 {\AA} (Ca2+ and Ba2+), while 5-coordination is preferred for divalent cations with larger (Ba2+) or smaller ionic radii (Mg2+).",
author = "{De Santis}, E. and Edwards, {Alison A.} and Alexander, {Bruce David} and Holder, {S. J.} and A.-S. Biesse-Martin and Nielsen, {B. V.} and Dharmit Mistry and L. Waters and G. Siligardi and Rabia Hussain and S. Faure and C. Taillefumier",
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De Santis, E, Edwards, AA, Alexander, BD, Holder, SJ, Biesse-Martin, A-S, Nielsen, BV, Mistry, D, Waters, L, Siligardi, G, Hussain, R, Faure, S & Taillefumier, C 2016, 'Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: A spectroscopic and computational study', Organic and Biomolecular Chemistry, vol. 14, no. 48, pp. 11371-11380. https://doi.org/10.1039/C6OB01954D

Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer : A spectroscopic and computational study. / De Santis, E.; Edwards, Alison A.; Alexander, Bruce David; Holder, S. J.; Biesse-Martin, A.-S.; Nielsen, B. V.; Mistry, Dharmit; Waters, L.; Siligardi, G.; Hussain, Rabia; Faure, S.; Taillefumier, C.

In: Organic and Biomolecular Chemistry, Vol. 14, No. 48, 2016, p. 11371-11380.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer

T2 - A spectroscopic and computational study

AU - De Santis, E.

AU - Edwards, Alison A.

AU - Alexander, Bruce David

AU - Holder, S. J.

AU - Biesse-Martin, A.-S.

AU - Nielsen, B. V.

AU - Mistry, Dharmit

AU - Waters, L.

AU - Siligardi, G.

AU - Hussain, Rabia

AU - Faure, S.

AU - Taillefumier, C.

PY - 2016

Y1 - 2016

N2 - We describe the qualitative and quantitative analysis of the complexation properties towards cations of a cyclic peptoid hexamer composed of alternating α- and β-peptoid monomers, which bear exclusively chiral (S)-phenylethyl side chains (spe) that have no noticeable chelating properties. The binding of a series of monovalent and divalent cations was assessed by 1H NMR, circular dichroism, fluorescence and molecular modelling. In contrast to previous studies on cations binding by 18-membered α-cyclopeptoid hexamers, the 21-membered cyclopeptoid cP1 did not complex monovalent cations (Na+, K+, Ag+) but showed selectivity for divalent cations (Ca2+, Ba2+, Sr2+ and Mg2+). Hexacoordinated C-3 symmetrical complexes were demonstrated for divalent cations with ionic radii around 1 Å (Ca2+ and Ba2+), while 5-coordination is preferred for divalent cations with larger (Ba2+) or smaller ionic radii (Mg2+).

AB - We describe the qualitative and quantitative analysis of the complexation properties towards cations of a cyclic peptoid hexamer composed of alternating α- and β-peptoid monomers, which bear exclusively chiral (S)-phenylethyl side chains (spe) that have no noticeable chelating properties. The binding of a series of monovalent and divalent cations was assessed by 1H NMR, circular dichroism, fluorescence and molecular modelling. In contrast to previous studies on cations binding by 18-membered α-cyclopeptoid hexamers, the 21-membered cyclopeptoid cP1 did not complex monovalent cations (Na+, K+, Ag+) but showed selectivity for divalent cations (Ca2+, Ba2+, Sr2+ and Mg2+). Hexacoordinated C-3 symmetrical complexes were demonstrated for divalent cations with ionic radii around 1 Å (Ca2+ and Ba2+), while 5-coordination is preferred for divalent cations with larger (Ba2+) or smaller ionic radii (Mg2+).

U2 - 10.1039/C6OB01954D

DO - 10.1039/C6OB01954D

M3 - Article

VL - 14

SP - 11371

EP - 11380

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 48

ER -