d5SICS is an artificial
nucleoside
Nucleosides are glycosylamines that can be thought of as nucleotides without a phosphate group. A nucleoside consists simply of a nucleobase (also termed a nitrogenous base) and a five-carbon sugar (ribose or 2'-deoxyribose) whereas a nucleotid ...
containing 6-methyl
isoquinoline
Isoquinoline is an individual chemical specimen - a heterocyclic aromatic organic compound - as well as the name of a family of many thousands of natural plant alkaloids, any one of which might be referred to as "an isoquinoline". It is a struc ...
-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
''Escherichia coli'' ( )Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. is a gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escherichia'' that is commonly foun ...
'' into which it was inserted.
The pairing of d5SICS–dNaM is mediated by packing and
hydrophobic force
The hydrophobic effect is the observed tendency of nonpolar substances to aggregate in an aqueous solution and to be excluded by water#Properties, water. The word hydrophobic literally means "water-fearing", and it describes the Segregation in m ...
s instead of
hydrogen bonding
In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...
, 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.
[ ]
References
Nucleosides
Synthetic biology
Thioketones
Nitrogen heterocycles
Heterocyclic compounds with 2 rings
Hydroxymethyl compounds
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