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2-Aminopurine: Difference between revisions

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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443313408
| Watchedfields = changed
⚫ | verifiedrevid = 477212531
| Name = 2-Aminopurine | Name = 2-Aminopurine
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = 2-Aminopurine.png | ImageFile = 2-Aminopurine.svg
| ImageSize = 200px | ImageSize = 230px
| ImageName = 2-Aminopurine | ImageName = 2-Aminopurine
| IUPACName = 7''H''-purin-2-amine | PIN = 9''H''-Purin-2-amine
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| InChI = 1/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10) | InChI = 1/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MWBWWFOAEOYUST-UHFFFAOYSA-N | StdInChIKey = MWBWWFOAEOYUST-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 452-06-2 | CASNo = 452-06-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O14B3U97FW
| PubChem = 9955 | PubChem = 9955
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 479072 | ChEBI = 479072
| SMILES = n1cc2c(nc1N)ncn2 | SMILES = Nc2ncc1ncc1n2
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
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'''2-Aminopurine''', an analog of ] and ], is a fluorescent molecular marker used in nucleic acid research.<ref>{{cite journal |author=Jean JM, Hall KB |title=2-Aminopurine fluorescence quenching and lifetimes: role of base stacking |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=98 |issue=1 |pages=37–41 |year=2001 |pmid=11120885 |url=http://www.pnas.org/cgi/pmidlookup?view=long&pmid=11120885 |doi=10.1073/pnas.011442198 |pmc=14540}}</ref> It most commonly pairs with ] as an adenine-analogue, but can also pair with ] as a guanine-analogue;.<ref>{{cite journal |author=Sowers LC, Fazakerley GV, Eritja R, Kaplan BE, Goodman MF |title=Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=83 |pages=5434–5438| year=1986 |url=http://www.pnas.org/content/83/15/5434 |doi=10.1073/pnas.83.15.5434 |pmid=3461441 |issue=15 |pmc=386301}}</ref> For this reason it is sometimes used in the laboratory for mutagenesis. '''2-Aminopurine''', a ] of ] and ], is a fluorescent molecular marker used in nucleic acid research.<ref>{{cite journal |vauthors=Jean JM, Hall KB |title=2-Aminopurine fluorescence quenching and lifetimes: role of base stacking |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=98 |issue=1 |pages=37–41 |year=2001 |pmid=11120885 |url=http://www.pnas.org/cgi/pmidlookup?view=long&pmid=11120885 |doi=10.1073/pnas.011442198 |pmc=14540|doi-access=free }}</ref> It most commonly pairs with ] as an adenine-analogue, but can also pair with ] as a guanine-analogue.<ref>{{cite journal |vauthors=Sowers LC, Fazakerley GV, Eritja R, Kaplan BE, Goodman MF |title=Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=83 |pages=5434–5438| year=1986 |doi=10.1073/pnas.83.15.5434 |pmid=3461441 |issue=15 |pmc=386301|bibcode=1986PNAS...83.5434S |doi-access=free }}</ref> For this reason it is sometimes used in the laboratory for mutagenesis.


==See also== ==See also==
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== References == == References ==

{{reflist}} {{reflist}}


{{DEFAULTSORT:Aminopurine, 2-}} {{DEFAULTSORT:Aminopurine, 2-}}
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Latest revision as of 18:11, 7 May 2023

2-Aminopurine
2-Aminopurine
2-Aminopurine
Names
Preferred IUPAC name 9H-Purin-2-amine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.545 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)Key: MWBWWFOAEOYUST-UHFFFAOYSA-N
  • InChI=1/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)Key: MWBWWFOAEOYUST-UHFFFAOYAC
SMILES
  • Nc2ncc1ncc1n2
Properties
Chemical formula C5H5N5
Molar mass 135.130 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2-Aminopurine, a purine analog of guanine and adenine, is a fluorescent molecular marker used in nucleic acid research. It most commonly pairs with thymine as an adenine-analogue, but can also pair with cytosine as a guanine-analogue. For this reason it is sometimes used in the laboratory for mutagenesis.

See also

References

  1. Jean JM, Hall KB (2001). "2-Aminopurine fluorescence quenching and lifetimes: role of base stacking". Proc. Natl. Acad. Sci. U.S.A. 98 (1): 37–41. doi:10.1073/pnas.011442198. PMC 14540. PMID 11120885.
  2. Sowers LC, Fazakerley GV, Eritja R, Kaplan BE, Goodman MF (1986). "Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR". Proc. Natl. Acad. Sci. U.S.A. 83 (15): 5434–5438. Bibcode:1986PNAS...83.5434S. doi:10.1073/pnas.83.15.5434. PMC 386301. PMID 3461441.
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