History of Nucleic Acid Chemistry: Difference between revisions

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=== Milestones ===
=== Milestones ===


==== Isolation of DNA ====
==== 1869 ⁠– Isolation of DNA ====
The person credited with being the first to isolate DNA was the Swiss physician Friedrich Miescher. He called the biochemical substance rich in phosphorus "nuclein". The initial work is dated as having occurred in early 1869.<sup>[1]</sup> Miescher worked at the University of Tübingen at the time, and did not know what the function of nuclein was.   
The person credited with being the first to isolate DNA was the Swiss physician Friedrich Miescher. He called the biochemical substance rich in phosphorus "nuclein". The initial work is dated as having occurred in early 1869.<ref>R. Dahm, Friedrich Miescher and the discovery of DNA. Devel. Biol. 2005, 278, 274-288. https://doi.org/10.1016/j.ydbio.2004.11.028</ref> Miescher worked at the University of Tübingen at the time, and did not know what the function of nuclein was.   


'''Structure of the DNA double helix'''
==== 1944 – DNA carries genetic information====
Avery determines that DNA carries genetic information.<ref>Avery OT et al., Journal of Experimental Medicine 79 (1944) p137-158.</ref>


The correct structure of the DNA double helix was published by Watson and Crick in two milestone papers in 1957.[2] The diffraction data was not from their own work, and the G:C base pair was incorrectly assumed to have only two hydrogen bonds. Still, the structure was a major breakthrough, as it explained how genetic information is stored and passed on to the next generation.
==== 1953 – Structure of the DNA double helix ====
The correct structure of the DNA double helix was published by Watson and Crick in two milestone papers in 1957.<ref>Watson, J. D.; Crick, F. H. Molecular structure of nucleic acids; a structure for deoxyribose nucleic acid. ''Nature'' '''1953''', ''171'', 737-738. https://doi.org/10.1038/171737a0</ref><ref>Watson, J. D.; Crick, F. H. Genetical implications of the structure of deoxyribonucleic acid. ''Nature'' '''1953''', ''171'', 964-967. https://doi.org/10.1038/171964b0
</ref> The diffraction data was not from their own work, and the G:C base pair was incorrectly assumed to have only two hydrogen bonds. Still, the structure was a major breakthrough, as it explained how genetic information is stored and passed on to the next generation.
<br><br>
Structure of base pairs:
<gallery heights=150 mode="packed">
File:Guanine Cytosine base pair red bond.png|Depiction of the G:C base pair with the hydrogen bond not yet identified in the 1957 paper highlighted in red.
File:Adenine Thymine base pair.png|Depiction of the A:T base pair.
</gallery>
 
==== 1956 – Phosphodiester chemistry ====
Khorana et al. establish phosphodiester chemistry for chain assembly in solution.<ref>Khorana HG et al. Chem. & Ind. London (1956), p. 1523.</ref>
 
==== 1965 – Phosphotriester chemistry ====
Letsinger and coworkers develop phosphotriester chemistry as improved method for solution-phase synthesis of DNA.<ref>Letsinger RL, Mahedevan V, J. Am. Chem. Soc. (1965), pp. 3526-3527.</ref>
 
==== 1970 – First synthesis of a gene ====
Khorana publishes the first synthesis of a gene (yeast alanine tRNA, 72mer via 19 fragments).<ref>Khorana HG, Nature 227 (1970), pp. 27-34.</ref>
 
==== 1977 – Solid phase DNA synthesis on polymeric support ====
Gait and Sheppard perform solid-phase DNA synthesis on a polymeric support.<ref>Gait MJ and Sheppard RC, NAR 4 (1977), pp. 1153 and 4391.</ref>
 
==== 1981 – Phosphoramidite approach ====
Building on the work of Letsinger, Beaucage and Caruthers demonstrate the superiority of the phosphoramidite approach.<ref>Beaucage SL and Caruthers MH, Tetrahedron Lett. 37 (1981), pp. 1859-1862.</ref>
 
==== 1984 – β-cyanoethyl phosphoramidite chemistry ====
Köster and Sinha patent ß-cyanoethyl phosphoramidite chemistry.<ref>Köster H & Sinha ND (1984), US Patent No. 4725677.</ref>
 
==== 1987 – 2'-o-TBDMS protection for RNA ====
Ogilvie reports 2´-O-TBDMS protection for RNA building blocks.<ref>Usman N et al., J. Am. Soc. Chem. (1957), pp. 7845-7854.</ref><ref>Ogilvie, K. K.; Sadana, K. L.;Thompson, E. A; Quilliam, M. A.; Westmore,. J. B. The use of silyl groups in protecting the hydroxyl functions of ribonucleosides. Tetrahedron Lett. 1974, 15, 2861-2863.</ref><ref>T. Wu; K. K. Ogilvie; R. T. Pon, Prevention of chain cleavage in the chemical synthesis of 2′-silylated oligoribonucleotides. Nucleic Acids Res. 1989, 17, 3501–3517.
</ref>
 
==== 1994 – Polymerase Chain Reaction ====
The polymerase chain reaction (PCR) was invented in the early 1980s by Kary B. Mullis while employed by Cetus Corporation. Mullis was awarded the Nobel Prize in Chemistry for his discovery in 1993.<ref>Mullis, K. B. The Polymerase Chain Reaction (Nobel Lecture). ''Angew. Chem. Int. Ed. Engl.'' '''1994''', ''33'', 1209-1213.</ref><ref>Process for amplifying nucleic acid sequences. US Patent US4683202A, filed on October 25, 1985.</ref>


== References ==
== References ==
[1] R. Dahm, Friedrich Miescher and the discovery of DNA. Devel. Biol. 2005, 278, 274-288. https://doi.org/10.1016/j.ydbio.2004.11.028
<references />
 
[2] a) Watson, J. D.; Crick, F. H. Molecular structure of nucleic acids; a structure for deoxyribose nucleic acid. ''Nature'' '''1953''', ''171'', 737-738. (b) Watson, J. D.; Crick, F. H. Genetical implications of the structure of deoxyribonucleic acid. ''Nature'' '''1953''', ''171'', 964-967. 

Latest revision as of 17:52, 25 September 2024

The History of Nucleic Acid Chemistry

Milestones

1869 ⁠– Isolation of DNA

The person credited with being the first to isolate DNA was the Swiss physician Friedrich Miescher. He called the biochemical substance rich in phosphorus "nuclein". The initial work is dated as having occurred in early 1869.[1] Miescher worked at the University of Tübingen at the time, and did not know what the function of nuclein was.

1944 – DNA carries genetic information

Avery determines that DNA carries genetic information.[2]

1953 – Structure of the DNA double helix

The correct structure of the DNA double helix was published by Watson and Crick in two milestone papers in 1957.[3][4] The diffraction data was not from their own work, and the G:C base pair was incorrectly assumed to have only two hydrogen bonds. Still, the structure was a major breakthrough, as it explained how genetic information is stored and passed on to the next generation.

Structure of base pairs:

  • Depiction of the G:C base pair with the hydrogen bond not yet identified in the 1957 paper highlighted in red.

    Depiction of the G:C base pair with the hydrogen bond not yet identified in the 1957 paper highlighted in red.

  • Depiction of the A:T base pair.

    Depiction of the A:T base pair.

1956 – Phosphodiester chemistry

Khorana et al. establish phosphodiester chemistry for chain assembly in solution.[5]

1965 – Phosphotriester chemistry

Letsinger and coworkers develop phosphotriester chemistry as improved method for solution-phase synthesis of DNA.[6]

1970 – First synthesis of a gene

Khorana publishes the first synthesis of a gene (yeast alanine tRNA, 72mer via 19 fragments).[7]

1977 – Solid phase DNA synthesis on polymeric support

Gait and Sheppard perform solid-phase DNA synthesis on a polymeric support.[8]

1981 – Phosphoramidite approach

Building on the work of Letsinger, Beaucage and Caruthers demonstrate the superiority of the phosphoramidite approach.[9]

1984 – β-cyanoethyl phosphoramidite chemistry

Köster and Sinha patent ß-cyanoethyl phosphoramidite chemistry.[10]

1987 – 2'-o-TBDMS protection for RNA

Ogilvie reports 2´-O-TBDMS protection for RNA building blocks.[11][12][13]

1994 – Polymerase Chain Reaction

The polymerase chain reaction (PCR) was invented in the early 1980s by Kary B. Mullis while employed by Cetus Corporation. Mullis was awarded the Nobel Prize in Chemistry for his discovery in 1993.[14][15]

References

  1. ↑ R. Dahm, Friedrich Miescher and the discovery of DNA. Devel. Biol. 2005, 278, 274-288. https://doi.org/10.1016/j.ydbio.2004.11.028
  2. ↑ Avery OT et al., Journal of Experimental Medicine 79 (1944) p137-158.
  3. ↑ Watson, J. D.; Crick, F. H. Molecular structure of nucleic acids; a structure for deoxyribose nucleic acid. Nature 1953, 171, 737-738. https://doi.org/10.1038/171737a0
  4. ↑ Watson, J. D.; Crick, F. H. Genetical implications of the structure of deoxyribonucleic acid. Nature 1953, 171, 964-967. https://doi.org/10.1038/171964b0
  5. ↑ Khorana HG et al. Chem. & Ind. London (1956), p. 1523.
  6. ↑ Letsinger RL, Mahedevan V, J. Am. Chem. Soc. (1965), pp. 3526-3527.
  7. ↑ Khorana HG, Nature 227 (1970), pp. 27-34.
  8. ↑ Gait MJ and Sheppard RC, NAR 4 (1977), pp. 1153 and 4391.
  9. ↑ Beaucage SL and Caruthers MH, Tetrahedron Lett. 37 (1981), pp. 1859-1862.
  10. ↑ Köster H & Sinha ND (1984), US Patent No. 4725677.
  11. ↑ Usman N et al., J. Am. Soc. Chem. (1957), pp. 7845-7854.
  12. ↑ Ogilvie, K. K.; Sadana, K. L.;Thompson, E. A; Quilliam, M. A.; Westmore,. J. B. The use of silyl groups in protecting the hydroxyl functions of ribonucleosides. Tetrahedron Lett. 1974, 15, 2861-2863.
  13. ↑ T. Wu; K. K. Ogilvie; R. T. Pon, Prevention of chain cleavage in the chemical synthesis of 2′-silylated oligoribonucleotides. Nucleic Acids Res. 1989, 17, 3501–3517.
  14. ↑ Mullis, K. B. The Polymerase Chain Reaction (Nobel Lecture). Angew. Chem. Int. Ed. Engl. 1994, 33, 1209-1213.
  15. ↑ Process for amplifying nucleic acid sequences. US Patent US4683202A, filed on October 25, 1985.
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