6-Methylisoxanthopterin

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6-Methylisoxanthopterin
6-Methylisoxanthopterin Structural Formula V.1.svg
Names
IUPAC name
2-Amino-6-methyl-1,8-dihydropteridine-4,7-dione
Other names
6-MI; 6MI
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.149.651 Edit this at Wikidata
UNII
  • InChI=1S/C7H7N5O2/c1-2-5(13)10-4-3(9-2)6(14)12-7(8)11-4/h1H3,(H4,8,10,11,12,13,14)
    Key: DYXQYFTUVSIKIG-UHFFFAOYSA-N
  • CC1=NC2=C(NC1=O)NC(=NC2=O)N
Properties
C7H7N5O2
Molar mass 193.166 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

6-Methylisoxanthopterin (6MI) is a base analog for the nucleotide guanine. It is useful as a fluorescent indicator because unlike most other base analogs, quenching does not occur when it is incorporated into a double helix. In fact, it exhibits a 3 to 4-fold increase in quantum yield when it is incorporated into a duplex formation.[1] This allows 6MI to be used to probe the dynamics of DNA or RNA helices using a technique such as fluorescence polarization anisotropy. [2]

See also[edit]

References[edit]

  1. ^ Moreno, Andrew (2016). "Photophysical Characterization of Enhanced 6-Methylisoxanthopterin Fluorescence in Duplex DNA". The Journal of Physical Chemistry B. 120 (48): 12232–12248. doi:10.1021/acs.jpcb.6b07369. PMID 27934220.
  2. ^ Shi, Xuesong (2009). "Probing the Dynamics of the P1 Helix within the Tetrahymena Group I Intron". Journal of the American Chemical Society. 131 (27): 9571–9578. doi:10.1021/ja902797j. PMC 2758093. PMID 19537712.