Controlling aromatic helix dimerization in water by tuning charge repulsions.
Journal
Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951
Informations de publication
Date de publication:
18 Oct 2023
18 Oct 2023
Historique:
received:
19
04
2023
accepted:
14
09
2023
medline:
20
10
2023
pubmed:
20
10
2023
entrez:
20
10
2023
Statut:
epublish
Résumé
Several helically folded aromatic oligoamides were designed and synthesized. The sequences were all water-soluble thanks to the charged side chains borne by the monomers. Replacing a few, sometimes only two, charged side chains by neutral methoxy groups was shown to trigger the formation of various aggregates which could be tentatively assigned to head-to-head stacked dimers of single helices, double helical duplexes and a quadruplex, none of which would form in organic solvent with organic-soluble analogues. The nature of the aggregates was supported by concentration and solvent dependent NMR studies,
Identifiants
pubmed: 37860656
doi: 10.1039/d3sc02020g
pii: d3sc02020g
pmc: PMC10583700
doi:
Types de publication
Journal Article
Langues
eng
Pagination
11251-11260Informations de copyright
This journal is © The Royal Society of Chemistry.
Déclaration de conflit d'intérêts
There are no conflicts to declare.
Références
Chemistry. 2005 Oct 21;11(21):6135-44
pubmed: 16075439
Science. 1991 Dec 6;254(5037):1497-500
pubmed: 1962210
ACS Cent Sci. 2021 Dec 22;7(12):2092-2098
pubmed: 34963901
Angew Chem Int Ed Engl. 2006 Aug 18;45(33):5483-6
pubmed: 16850517
Chem Commun (Camb). 2016 Jan 14;52(4):669-72
pubmed: 26507120
Angew Chem Int Ed Engl. 2020 May 4;59(19):7478-7486
pubmed: 32198909
Chem Sci. 2022 Apr 7;13(17):4915-4921
pubmed: 35655878
Acc Chem Res. 2016 Apr 19;49(4):646-54
pubmed: 26954326
Chem Sci. 2017 Oct 1;8(10):7251-7257
pubmed: 29147547
Org Biomol Chem. 2023 May 3;21(17):3525-3530
pubmed: 37070553
Nat Commun. 2022 Apr 27;13(1):2273
pubmed: 35477706
Nat Chem. 2018 May;10(5):511-518
pubmed: 29610464
J Am Chem Soc. 2012 Sep 26;134(38):15656-9
pubmed: 22950783
Chemistry. 2009 Nov 2;15(43):11530-6
pubmed: 19768708
Angew Chem Int Ed Engl. 2022 Mar 7;61(11):e202116509
pubmed: 34962351
Angew Chem Int Ed Engl. 2023 Feb 1;62(6):e202214194
pubmed: 36478069
Chem Asian J. 2010 Jun 1;5(6):1364-75
pubmed: 20376877
Org Lett. 2014 Oct 3;16(19):4992-5
pubmed: 25211182
J Am Chem Soc. 2013 Sep 25;135(38):14401-12
pubmed: 24028552
Chem Commun (Camb). 2016 Mar 11;52(20):3939-42
pubmed: 26878701
Angew Chem Int Ed Engl. 2008;47(9):1715-8
pubmed: 18214871
Angew Chem Int Ed Engl. 2006 Jul 10;45(28):4625-8
pubmed: 16789035
Chem Asian J. 2013 Jul;8(7):1579-86
pubmed: 23650280
Nat Nanotechnol. 2021 Aug;16(8):911-917
pubmed: 34017100
Angew Chem Int Ed Engl. 2021 Apr 6;60(15):8380-8384
pubmed: 33475210
J Am Chem Soc. 2021 Mar 24;143(11):4346-4358
pubmed: 33688731
J Am Chem Soc. 2004 Nov 17;126(45):14858-64
pubmed: 15535712
Angew Chem Int Ed Engl. 2010 Mar 1;49(10):1778-81
pubmed: 20135659
Acc Chem Res. 2018 Apr 17;51(4):970-977
pubmed: 29589916
Org Lett. 2019 Apr 19;21(8):2555-2559
pubmed: 30920225
J Am Chem Soc. 2016 Oct 19;138(41):13568-13578
pubmed: 27652807
Chem Commun (Camb). 2021 Apr 27;57(34):4130-4133
pubmed: 33908492
J Am Chem Soc. 2016 Mar 2;138(8):2749-54
pubmed: 26877246
J Org Chem. 2018 Feb 16;83(4):1898-1902
pubmed: 29368516
Chempluschem. 2021 Mar;86(3):496-503
pubmed: 33755326
Chem Rev. 2020 Mar 11;120(5):2759-2782
pubmed: 32039583
Chem Soc Rev. 2010 Oct;39(10):3664-74
pubmed: 20730154
J Am Chem Soc. 2017 Jul 12;139(27):9350-9358
pubmed: 28609621
J Am Chem Soc. 2003 Mar 26;125(12):3448-9
pubmed: 12643704
J Am Chem Soc. 2018 Nov 14;140(45):15477-15486
pubmed: 30346756
J Am Chem Soc. 2004 Dec 22;126(50):16528-37
pubmed: 15600357
J Am Chem Soc. 2018 Dec 19;140(50):17711-17723
pubmed: 30465607
Nat Commun. 2019 Feb 18;10(1):801
pubmed: 30778067
Science. 1997 Sep 19;277(5333):1793-6
pubmed: 9295264
J Am Chem Soc. 2004 Oct 6;126(39):12386-94
pubmed: 15453772
J Am Chem Soc. 2017 Nov 29;139(47):17098-17108
pubmed: 29058422
Nat Chem. 2018 Jan;10(1):51-57
pubmed: 29256508
Angew Chem Int Ed Engl. 2018 Dec 3;57(49):16109-16113
pubmed: 30324741
J Org Chem. 2022 Mar 4;87(5):3686-3690
pubmed: 35023738
Angew Chem Int Ed Engl. 2016 Sep 26;55(40):12398-402
pubmed: 27411932
J Am Chem Soc. 2009 Apr 8;131(13):4710-9
pubmed: 19334774
Angew Chem Int Ed Engl. 2022 Jul 11;61(28):e202200259
pubmed: 35384207
J Org Chem. 2011 Jun 17;76(12):4841-58
pubmed: 21542644
Chemistry. 2023 Jun 27;29(36):e202300898
pubmed: 37024428
Chem Sci. 2017 May 1;8(5):3741-3749
pubmed: 28553532
J Am Chem Soc. 2021 Mar 3;143(8):3191-3204
pubmed: 33596052
Chem Sci. 2021 May 20;12(24):8342-8352
pubmed: 34221315
Chem Commun (Camb). 2003 Jan 7;(1):56-7
pubmed: 12610963
Org Lett. 2008 Dec 4;10(23):5373-6
pubmed: 18973333
Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13140-4
pubmed: 25284711
Chem Commun (Camb). 2023 Apr 27;59(35):5253-5256
pubmed: 37043279
J Am Chem Soc. 2006 Jun 7;128(22):7176-8
pubmed: 16734467
Chem Commun (Camb). 2012 Apr 24;:
pubmed: 22531290
Chem Commun (Camb). 2019 Sep 10;55(73):10968-10971
pubmed: 31451818
J Am Chem Soc. 2005 Sep 7;127(35):12214-5
pubmed: 16131186
Chem Sci. 2023 Mar 31;14(18):4759-4768
pubmed: 37181781