2,6-Diaminopurine

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2,6-Diaminopurine
2,6-Diaminopurine.svg
Names
IUPAC name
7H-Purine-2,6-diamine
Other names
2-Aminoadenine
Identifiers
1904-98-9 N
ChEMBL ChEMBL388596 YesY=
ChemSpider 28738 YesY
Jmol-3D images Image
PubChem 30976
Properties
C5H6N6
Molar mass 150.15 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).
 N
Infobox references

2,6-Diaminopurine is a compound used to treat leukemia.[citation needed]

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.[1][2][3]

Cyanophage S-2L[edit]

In Cyanophage S-2L, diaminopurine (DAP) is used instead of adenine (host evasion).[4] Diaminopurine basepairs perfectly with thymine as it is identical to adenine but has an amine group at position 2 forming 3 intramolecular hydrogen bonds, eliminating the major difference between the two types of basepairs (Weak:A-T and Strong:C-G). This improved stability affects protein-binding interactions that rely on those differences.

References[edit]

  1. ^ 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". PNAS. doi:10.1073/pnas.1106493108. Retrieved 2011-08-15. 
  2. ^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. Retrieved 2011-08-10. 
  3. ^ ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests". ScienceDaily. Retrieved 2011-08-09. 
  4. ^ Kirnos MD, Khudyakov IY, Alexandrushkina NI, Vanyushin BF. 2-aminoadenine is an adenine substituting for a base in S-2L cyanophage DNA. Nature. 1977 Nov 24;270(5635):369–70.