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Cited by 196DNA and Nucleic Acid ChemistryRNA and protein synthesis mechanismsAdvanced biosensing and bioanalysis techniques

Artificially expanded genetic information system: a new base pair with an alternative hydrogen bonding pattern

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Yang, Zunyi, Hutter, Daniel, Sheng, Pinpin, Sismour, A. Michael, Benner, Steven A.·2006·Nucleic Acids Research
DOI 10.1093/nar/gkl633PMC PMC1635279
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Abstract

To support efforts to develop a 'synthetic biology' based on an artificially expanded genetic information system (AEGIS), we have developed a route to two components of a non-standard nucleobase pair, the pyrimidine analog 6-amino-5-nitro-3-(1'-beta-D-2'-deoxyribofuranosyl)-2(1H)-pyridone (dZ) and its Watson-Crick complement, the purine analog 2-amino-8-(1'-beta-D-2'-deoxyribofuranosyl)-imidazo[1,2-a]-1,3,5-triazin-4(8H)-one (dP). These implement the pyDDA:puAAD hydrogen bonding pattern (where 'py' indicates a pyrimidine analog and 'pu' indicates a purine analog, while A and D indicate the hydrogen bonding patterns of acceptor and donor groups presented to the complementary nucleobases, from the major to the minor groove). Also described is the synthesis of the triphosphates and protected phosphoramidites of these two nucleosides. We also describe the use of the protected phosphoramidites to synthesize DNA oligonucleotides containing these AEGIS components, verify the absence of epimerization of dZ in those oligonucleotides, and report some hybridization properties of the dZ:dP nucleobase pair, which is rather strong, and the ability of each to effectively discriminate against mismatches in short duplex DNA.

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  • Only four bases are used in nucleic acids when others are also possible.

    “For example, the amino acids used by life show little correlation with abiotic synthesis of amino acids (Ward and Benner, 2007), and only four bases are used in nucleic acids when others are also possible (Benner and Sismour, 2005; Yang et al., 2006).”

    From The Astrobiology Primer v2.0 (2016) · cites this paper as Yang et al., 2006

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Authors
Yang, Z., Hutter, D., Sheng, P., Sismour, A. M., & Benner, S. A.
Affiliations
Foundation for Applied Molecular Evolution (US)
Corresponding author
Benner, Steven A.
ORCID
Venue
Nucleic Acids Research
Publisher
Oxford University Press (OUP)
Published
2006-10-29
Volume
34
Issue
21
Pages
6095-6101
ISSN
  • 0305-1048 (ISSN-L)
  • 1362-4962
DOI
10.1093/nar/gkl633
PMC
PMC1635279
OpenAlex
W2104694288
Cited by
196
References
2
Citations by year
2026: 4 · 2025: 9 · 2024: 11 · 2023: 15 · 2022: 8 · 2021: 13 · 2020: 7 · 2019: 17 · 2018: 8 · 2017: 7 · 2016: 22 · 2015: 7 · 2014: 8 · 2013: 7 · 2012: 12
FWCI
2.72
Type
journal article
Language
en
Open access
Licence
cc-by-nc
Locations
  • Nucleic Acids Research (publishedVersion, cc-by-nc)
  • Europe PMC (PubMed Central) (publishedVersion)
  • PubMed Central (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • National Aeronautics and Space Administration
  • National Institutes of Health
  • National Institute of General Medical Sciences (GM-54048, R01GM054048)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Advanced biosensing and bioanalysis techniques
Keywords
Watson-Crick complementarity, nucleoside triphosphates, phosphoramidite synthesis, epimerization, nucleic acid hybridization, mismatch discrimination, synthetic biology
MeSH terms
Deoxyribonucleosides, Hydrogen Bonding, Isomerism, Nucleic Acid Denaturation, Nucleic Acid Hybridization, Nucleosides, Nucleotides, Oligonucleotides, Organophosphorus Compounds, Pyridones, Temperature, Triazines, Base Pairing, Base Pair Mismatch

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