This article is about a benzo-homologated DNA analogue. For multiple video card technology by Diamond Multimedia, see xDNA (multi-graphics). For other alternative nucleic acid coding systems, see nucleic acid analogues.
Benzo-homologated Adenine
Benzo-homologated Thymine
Benzo-homologated Cytosine
Benzo-homologated Guanine
xDNA (also known as expanded DNA or benzo-homologated DNA) is a size-expanded nucleotide system synthesized from the fusion of a benzene ring and one of the four natural bases: adenine, guanine, cytosine, and thymine.[1] This size expansion produces an 8 letter alphabet which has a larger information storage capacity than natural DNA's (often referred to as B-DNA in literature) 4 letter alphabet.[2] As with normal base-pairing, A pairs with xT, C pairs with xG, G pairs with xC, and T pairs with xA. The double helix is thus 2.4Å wider than a natural double helix.[3][4] While similar in structure to B-DNA, xDNA has unique absorption, fluorescence, and stacking properties.[5][6][7]
Initially synthesized as an enzyme probe by Nelson J. Leonard's group, benzo-homologated adenine was the first base synthesized. Later, Eric T. Kool's group finished synthesizing the remaining three expanded bases, eventually followed by yDNA ("wide" DNA), another benzo-homologated nucleotide system, and naphtho-homologated xxDNA and yyDNA. xDNA is more stable when compared to regular DNA when subjected to higher temperature, and while entire strands of xDNA, yDNA, xxDNA and yyDNA exist, they are currently difficult to synthesize and maintain. Experiments with xDNA provide new insight into the behavior of natural B-DNA. The extended bases xA, xC, xG, and xT are naturally fluorescent, and single strands composed of only extended bases can recognize and bind to single strands of natural DNA, making them useful tools for studying biological systems.[3][8] xDNA is most commonly formed with base pairs between a natural and expanded nucleobase, however x-nucleobases can also be paired together.[5] Current research supports xDNA as a viable genetic encoding system in the near future.[4]
^Lynch SR, Liu H, Gao J, Kool ET (November 2006). "Toward a designed, functioning genetic system with expanded-size base pairs: solution structure of the eight-base xDNA double helix". Journal of the American Chemical Society. 128 (45): 14704–11. doi:10.1021/ja065606n. PMC 2519095. PMID 17090058.
^Gao J, Liu H, Kool ET (May 2005). "Assembly of the complete eight-base artificial genetic helix, xDNA, and its interaction with the natural genetic system". Angewandte Chemie. 44 (20): 3118–22. doi:10.1002/anie.200500069. PMID 15834852.
^ abFuentes-Cabrera M, Zhao X, Kent PR, Sumpter BG (August 2007). "Electronic structure of xDNA". The Journal of Physical Chemistry B. 111 (30): 9057–61. doi:10.1021/jp0729056. PMID 17650925.
^ abKrueger AT, Lu H, Højland T, Liu H, Gao J, Kool ET (2008-09-01). "Towards the replication of xDNA, a size-expanded unnatural genetic system". Nucleic Acids Symposium Series. 52 (1): 455–6. doi:10.1093/nass/nrn231. PMID 18776450.
^ abMcConnell TL, Wetmore SD (March 2007). "How do size-expanded DNA nucleobases enhance duplex stability? Computational analysis of the hydrogen-bonding and stacking ability of xDNA bases". The Journal of Physical Chemistry B. 111 (11): 2999–3009. doi:10.1021/jp0670079. PMID 17388411.
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