202129-70-2Relevant academic research and scientific papers
Oligonucleotides with (N-thymin-1-ylacetyl)-1-arylserinol backbone: Chiral acyclic analogs with restricted conformational flexibility
Rana, Vipul S,Kumar, Vaijayanti A,Ganesh, Krishna N
, p. 1311 - 1321 (2007/10/03)
All four threoerythro stereoisomers of 2(R/S)-(N-thymin-1-ylacetyl)-amino-1(R/S)-aryl-1,3-propanediol were synthesized from 2(R/S)-amino-1(R/S)-aryl-1,3-propanediol in 45-50% overall yield. The inversion of the C1 hydroxyl group in (1S, 2S), 4a, and (1R, 2R), 4d, was accomplished under Mitsunobu conditions to get (1R, 2S), 4c, and (1S, 2R), 4e isomers, respectively. Compounds 4a-f were individually converted into their respective amidite synthons 5a-f. All these stereoisomers were individually incorporated into oligonucleotides (ODNs) at pre-determined positions and various biophysical studies of their hybrids with complementary DNA were carried out. All the four stereoisomers when present at 3′/5′ terminal positions in the ODNs were almost equally efficient in their binding capacity as the natural oligomers, with (1S, 2S) being marginally favored over other stereoisomers. The incorporation of these chiral acyclic nucleosides also protected the ODN against enzymatic degradation.
Oligonucleotides with (N-thymin-1-ylacetyl)1-phenylserinol in backbone: Chiral acyclic analogues that form DNA triplexes
Rana, Vipul S.,Kumar, Vaijayanti A.,Ganesh, Krishna N.
, p. 2837 - 2842 (2007/10/03)
The synthesis of oligonucleotides containing chiral acyclic 2(R/S)-(N- thymin-1-ylacetyl)-amino-1 (R/S)-phenyl-1,3-propanediol unit in the backbone (I, R=Ar) is described. When used as third strand of a triplex with complementary natural duplex, the modified oligonucleotides form stable triplexes with triplex duplex transition Tm dependent on the number, position and stereochemistry of modification.
