Structure/Activity Relationship

The following products are used to investigate the effect on the activity of an oligonucleotide when key structural elements are changed.  The 7-deaza purine monomers lack groups critical for hydrogen bonding.  7-Deaza-8-aza-A and 7-deaza-8-aza-G (PPG) monomers are isomers of A and G and have similar electron density.  Their presence in oligos is slightly stabilizing relative to A and G.  Unlike G, PPG does not lead to aggregation and G-rich oligos can be easily prepared and isolated.  5’-Fluorescein oligos with PPG at the 5’-terminus are much less quenched than the equivalent G oligos.  As a purine analogue of Thymidine, 7-deaza-2’-deoxyXanthosine (7-deaza-dX) promises to have interesting effects on DNA structure of triplexes.  7-Deaza-dX also forms a non-standard base pair with a 2,4-diaminopyrimidine nucleoside analogue.  Standard nucleobases have an unshared pair of electrons that project into the minor groove of duplex DNA.  Enzymes that interact with DNA, polymerases, reverse transcriptases, restriction enzymes, etc., may use a hydrogen bond donating group to contact the hydrogen bond acceptor in the minor groove.  3-Deaza-2’-deoxyadenosine is very interesting in that it maintains the ability for regular Watson-Crick hydrogen bonding to T but is lacking the electron pair at the 3-position normally provided by N3. 

INTELLECTUAL PROPERTY

The use of PPG is subject to proprietary rights of ELITechGroup and it is sold under license from ELITechGroup.

(1) I.V. Kutyavin, et al., Nucleic Acids Res., 2002, 30, 4952-4959.

The C-nucleoside 2’-deoxypseudouridine, in contrast to dU, forms stable C:pseudoU-A triplets.  2-Aminopurine lacks groups critical for hydrogen bonding and is a mildly fluorescent base.

Demand for sulfur modified bases continues to expand for investigations of oligonucleotide structure, but primarily for cross-linking purposes.  6-Thio-dG, 4-Thio-dT and 4-thio-dU are very useful modifications for photo cross-linking and photoaffinity labeling experiments.  Oligos containing 2-thio-dT are useful in examining protein-DNA interaction by acting as photosensitizing probes.   The thiocarbonyl group in 2-thio-dT is especially interesting in that it is available to react with compounds associating with the minor groove of DNA.  2-Amino-A forms a very stable base pair with T containing three hydrogen bonds but the stability of the base pair with 2-thio-T is greatly diminished.  Due to steric interactions between the 2-thio group of thymidine and the 2-amino group of 2-amino-A, the base pair contains only a single hydrogen bond.  Oligos containing 2-amino-dA and 2-thio-dT exhibit high affinity for natural oligonucleotides but show little affinity for other similar oligos even of a complementary sequence. 

8-Amino-dA and 8-amino-dG are useful in triplex formation due to the presence of the additional amino groups.

2’-DeoxyXanthosine (dX) is a naturally occurring nucleoside that may be derived from oxidative deamination of 2’-deoxyGuanosine (dG).  dX has a similar bonding pattern to thymidine and it may base pair with dA, with such purine-purine interactions causing duplex distortion.  dX also featured in attempts to extend the genetic alphabet with a new base pair of dX and pyrimidine-2,4-diamine nucleoside.  dX has also interested researchers in the field of DNA damage and repair since it is a product of nitric oxide-induced mutagenesis.

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