Metal-mediated base pairing within the simplified nucleic acid GNA

被引：45

作者：

Schlegel, Mark K. ^{[1
]}

Zhang, Lilu ^{[1
]}

Pagano, Nicholas ^{[1
]}

Meggers, Eric ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 03期

关键词：

DUPLEX FORMATION; ARTIFICIAL DNA; IONS;

D O I：

10.1039/b816142a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroxypyridone and pyridopurine homo- and hetero-base pairs have been investigated in the context of duplex GNA (glycol nucleic acid). Phosphoramidites for automated GNA solid phase synthesis were synthesized economically in a few steps starting from commercially available enantiopure glycidol. Similar to their behavior in DNA, the hydroxypyridone and pyridopurine homo-base pairs display a metal-dependent base pairing, with the hydroxypyridone base pair exhibiting a preference for copper(II) ions and the pyridopurine a preference for nickel( II) ions. However, these metallo-base pairs show modulated properties in GNA with respect to metal-dependent pairing stabilities and metal selectivities. Most interestingly, the hydroxypyridone homo-base pair and hydroxypyridone-pyridopurine hetero-base pair are particularly well accommodated in the GNA duplex and form copper( II)-dependent base pairs that are more stable compared to a Watson-Crick A: T base pair at the same position by nearly 20 degrees C and 24 degrees C, respectively. The structure of the copper( II)-hydroxypyridone homo-base pair is discussed based on a recent metallo-GNA duplex crystal structure.

引用

页码：476 / 482

页数：7

共 42 条

[1] Structure of a copper-mediated base pair in DNA [J].

Atwell, S ;

Meggers, E ;

Spraggon, G ;

Schultz, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) :12364-12367

[2] Understanding nucleic acids using synthetic chemistry [J].

Benner, SA .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (10) :784-797

[3] Conformational change induced by metal-ion-binding to DNA containing the artificial 1,2,4-triazole nucleoside [J].

Bohme, Dominik ;

Dupre, Nicole ;

Megger, Dominik A. ;

Muller, Jens .

INORGANIC CHEMISTRY, 2007, 46 (24) :10114-10119

[4] A highly DNA-duplex-stabilizing metal-salen base pair [J].

Clever, GH ;

Polborn, K ;

Carell, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7204-7208

[5] DNA-metal base pairs [J].

Clever, Guido H. ;

Kaul, Corinna ;

Carell, Thomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (33) :6226-6236

[6] Controlled stacking of 10 transition-metal ions inside a DNA duplex [J].

Clever, Guido H. ;

Carell, Thomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (1-2) :250-253

[7] Metal-salen-base-pair complexes inside DNA:: Complexation overrides sequence information [J].

Clever, Guido H. ;

Soeltl, Yvonne ;

Burks, Heather ;

Spahl, Werner ;

Carell, Thomas .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (34) :8708-8718

[8] Chemical etiology of nucleic acid structure [J].

Eschenmoser, A .

SCIENCE, 1999, 284 (5423) :2118-2124

[9] The ups and downs of nucleic acid duplex stability: structure-stability studies on chemically-modified DNA:RNA duplexes [J].

Freier, SM ;

Altmann, KH .

NUCLEIC ACIDS RESEARCH, 1997, 25 (22) :4429-4443

[10] Artificial oligopeptide scaffolds for stoichiometric metal binding [J].

Gilmartin, BP ;

Ohr, K ;

McLaughlin, RL ;

Koerner, R ;

Williams, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (26) :9546-9555

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