250708-44-2

Upstream product

• 250708-29-3 1-{5-azido-3-O-benzyl-4-[(benzyloxy)methyl]-5-deoxy-α-L-lyxofuranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione 
• 74-88-4 methyl iodide 
• 1400815-02-2 4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)-2’-O-methylthymidine 
• 1400815-01-1 2’-O-acetyl-4’-C-azidomethyl-3’,5’-di-O-benzyl-3-(4-methoxybenzyl)thymidine 
• 250708-41-9 1-{2-O-acetyl-5-azido-3-O-benzyl-4-[(benzyloxy)methyl]-5-deoxy-α-L-lyxothranosyl}-5-methylpyrimidine-2,4-(1H,3H)-dione 
• 65-71-4 thymin 

Downstream Products

• 250708-38-4 1-{5-deoxy-4-C-{[(4,4'-dimethoxytrityl)oxy]methyl}-2-O-methyl-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine 
• 250708-40-8 1-{3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-5-[(trifluoroacetyl)amino]-α-L-lyxofuranosyl}thymine 
• 250708-37-3 1-{5-amino-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-2-O-methyl-α-L-lyxofuranosyl}thymine 

Relevant academic research and scientific papers

Incorporation of 4′-C-aminomethyl-2′-O-methylthymidine into DNA by thermophilic DNA polymerases

The dual modified nucleotide 4′-C-aminomethyl-2′-O- methylthymidine 5′-triphosphate was synthesized and enzymatically incorporated into DNA by the thermophilic DNA polymerases Pfu and Therminator III. The dual ribose modification imparted increased exonuclease resistance to DNA compared to the well-known 2′-O-methyl modification.

Oligonucleotides containing novel 4'-C- or 3'-C-(aminoalkyl)-branched thymidines

The synthesis of four novel 3'-C-branched and 4'-C-branched nucleosides and their transformation into the corresponding 3'-O-phosphoramidite building blocks for automated oligonucleotide synthesis is reported. The 4'-C-branched key intermediate 11 was synthesized by a convergent strategy and converted to its 2-O-methyl and 2'-deoxy-2'-fluoro derivatives, leading to the preparation of novel oligonucleotide analogues containing 4'-C-(aminomethyl)-2'-O-methyl monomer X and 4'-C-(aminomethyl)-2'-deoxy-2'-fluoro monomer Y (Schemes 2 and 3). In general, increased binding affinity towards complementary single- stranded DNA and RNA was obtained with these analogues compared to the unmodified references (Table 1). The presence of monomer X or monomer Y in a 2'-O-methyl-RNA oligonucleotide had a negative effect on the binding affinity of the 2'-O-methyl-RNA oligonucleotide towards DNA and RNA. Starting from the 3'-C-allyl derivative 28, 3'-C-(3-aminopropyl)-protected nucleosides and 3'- O-phosphoramidite derivatives were synthesized, leading to novel oligonucleotide analogues containing 3'-C-(3-aminopropyl)thymidine monomer Z or the corresponding 3'-C-(3-aminopropyl)-2'-O,5-dimethyluridine monomer W (Schemes 4 and 5). Incorporation of the 2'-deoxy monomer Z induced no significant changes in the binding affinity towards DNA but decreased binding affinity towards RNA, while the 2'-O-methyl monomer Z induced decreased binding affinity towards DNA as well as RNA complements (Table 2).

Oligonucleotides containing 4'-C-aminomethyl-2'-modified thymidines show increased binding affinity towards DNA and RNA

Oligonucleotides containing 4'-C-aminomethyl-2'-O-methyl or 4'-C-aminomethyl-2'-deoxy-2'-fluoro modified thymidines have been synthesized. Compared with the corresponding oligodeoxynucleotide reference these novel oligonucleotide analogues display increased binding affinity towards complementary single stranded DNA as well as RNA. The possible effect of the positively charged 4'-C-aminomethyl group has been investigated.