2,6-Diaminopurine

2,6-Diaminopurine
Names
IUPAC name
7H-purine-2,6-diamine
Other names
2-aminoadenine; 2,6-DAP
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.016.006 Edit this at Wikidata
UNII
  • InChI=1S/C5H6N6/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H5,6,7,8,9,10,11) checkY=
    Key: MSSXOMSJDRHRMC-UHFFFAOYSA-N checkY=
  • InChI=1S/C5H6N6/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H5,6,7,8,9,10,11)
  • Nc1nc(N)nc2c1nc[nH]2
Properties
C5H6N6
Molar mass 150.145 g·mol−1
Appearance White to yellow crystalline powder
Density 1.743 g/cm3
Melting point 117 to 122 °C (243 to 252 °F; 390 to 395 K)
2.38 g/L at 20 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,6-diaminopurine (2,6-DAP, also known as 2-aminoadenine) is a compound once used in the treatment of leukemia.[1] As the Z base, it is found instead of adenine (A) in the genetic material of some bacteriophage viruses.[2]

In August 2011, a report, based on NASA studies with meteorites found on Earth, was published suggesting 2,6-diaminopurine and related organic molecules, including the DNA and RNA components adenine and guanine, may have been formed extraterrestrially in outer space.[3][4][5]

  1. ^ "George H. Hitchings". nobelprize.org.
  2. ^ "Some viruses thwart bacterial defenses with a unique genetic alphabet". 5 May 2021.
  3. ^ Callahan, M.P.; Smith, K.E.; Cleaves, H.J.; Ruzica, J.; Stern, J.C.; Glavin, D.P.; House, C.H.; Dworkin, J.P. (11 August 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases". Proceedings of the National Academy of Sciences. 108 (34). PNAS: 13995–13998. Bibcode:2011PNAS..10813995C. doi:10.1073/pnas.1106493108. PMC 3161613. PMID 21836052.
  4. ^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. Retrieved 2011-08-10.
  5. ^ ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests". ScienceDaily. Retrieved 2011-08-09.