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Macrochelation, cyclometallation and G-quartet formation: N3- and C8-bound PdII complexes of adenine and guanine

Lookup NU author(s): Clayton Price, Michelle Shipman, Dr Mark Elsegood, Emeritus Professor Bill Clegg, Professor Andrew Houlton

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Abstract

The reactions of PdII ions with a series of chelate-tethered derivatives of adenine and guanine have been studied and reveal a difference in the reactivity of the purine bases. Reactions of [PdCl2(MeCN)2] and A-alkyl-enH · Cl (alkyl = propyl or ethyl, A = adenine, en = ethylenediamine) yield the monocationic species [PdCl(A-N3-Et-en)]+ (1) and [PdCl(A-N3-Pr-en)]+ (2). Both involve co-ordination at the minor groove site N3 of the nucleobase as confirmed by single-crystal X-ray analysis. Reactions with the analogous G-alkyl-enH · Cl derivatives (G = guanine, alkyl = ethyl or propyl) were more complex with a mixture of species being observed. For G-Et-en · HCl a product was isolated which was identified as [PdCl(G-C8-Et-en)]+ (3). This compound contains a biomolecular metal-carbon bond involving C8 of the purine base. Crystallography of a product obtained from reaction of G-Pr-enH · Cl and [Pd(MeCN)4][NO3]2 reveals an octacationic tetrameric complex (4), in which each ligand acts to bridge two metal ions through a combination of a tridentate binding mode involving the diamine and N3 and monodentate coordination at N7.


Publication metadata

Author(s): Elsegood MRJ; Shipman MA; Clegg W; Houlton A; Price C; Rees NH; Edwards AJ

Publication type: Article

Publication status: Published

Journal: Chemistry - A European Journal

Year: 2001

Volume: 7

Issue: 6

Pages: 1194-1201

ISSN (print): 0947-6539

ISSN (electronic): 1521-3765

Publisher: Wiley - VCH Verlag GmbH & Co

URL: http://dx.doi.org/10.1002/1521-3765(20010316)7:6<1194::AID-CHEM1194>3.0.CO;2-3

DOI: 10.1002/1521-3765(20010316)7:6<1194::AID-CHEM1194>3.0.CO;2-3

PubMed id: 11322545


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