d5SICS

d5SICS
Haworth projection of d5SICS
Ball-and-stick model of d5SICS
Names
IUPAC name
2-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-methylisoquinoline-1(2H)-thione
Systematic IUPAC name
2-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylisoquinoline-1(2H)-thione
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C15H17NO3S/c1-9-2-3-11-10(6-9)4-5-16(15(11)20)14-7-12(18)13(8-17)19-14/h2-6,12-14,17-18H,7-8H2,1H3/t12-,13+,14+/m0/s1
    Key: ISOKBQJGUJTDAE-BFHYXJOUSA-N
  • OCC3OC(N2C=Cc1cc(ccc1C2=S)C)CC3(O)
  • Cc1ccc2c(c1)ccn(c2=S)[C@H]3C[C@@H]([C@H](O3)CO)O
Properties
C15H17NO3S
Molar mass 291.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

d5SICS is an artificial nucleoside containing 6-methylisoquinoline-1-thione-2-yl group instead of a base.

It pairs up with dNaM in a hydrophobic interaction. It was not able to be removed by the error-correcting machinery of the E. coli into which it was inserted. The pairing of d5SICS–dNaM is mediated by packing and hydrophobic forces instead of hydrogen bonding, which occurs in natural base pairs. Therefore, in free DNA, rings of d5SICS and dNaM are placed in parallel planes instead of the same plane. The d5SICS-dNaM pairing replaced an older dNaM-dTPT3 pairing.


This page was last updated at 2024-04-17 22:03 UTC. Update now. View original page.

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