357281-99-3

Upstream product

• 3601-90-9 5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate 
• 5804-85-3 diethylaluminium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 357282-03-2 β-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside 
• 357282-05-4 α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside 
• 357282-02-1 2-nitrobenzyl 1'-cyano-2'-deoxy-D-ribofuranoside 
• 800387-66-0 β-1'-[N-allyloxycarbonyl(aminomethyl)]-5'-(dimethoxytrityl)thymidine 
• 800387-64-8 C₂₉H₂₇Cl₂N₃O₉ 
• 1053702-75-2 C₂₅H₂₃Cl₂N₃O₇ 
• 800387-68-2 1'-cyano-3',5'-bis-O-(p-chlorobenzoyl)thymidine 
• 357282-00-9 1-bromo-3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-D-ribofuranosyl cyanide 

Relevant academic research and scientific papers

Synthesis of a 1′-aminomethylthymidine and oligodeoxyribonucleotides with 1′-acylamidomethylthymidine residues

Reported here is a 10-step synthesis of a phosphoramidite building block of 1′-aminomethylthymidine that starts from 2-deoxyribose. The framework of the branched aminonucleoside was elaborated from a known 1-cyano-1-bromo glycosyl donor, whose reaction with the silylated nucleobase furnished the 1′-cyanide, which was reduced to the desired aminomethylnucleoside. The N-allyloxycarbonyl (Alloc)-protected nucleoside was converted to a phosphoramidite building block and incorporated into the oligonucleotides 5′-GCAT*TATTAC-3′, and 5′-GCAT*TAT*TAC- 3′, where T* denotes 1′-acylamidomethylthymidine residues. Removal of the Alloc protecting group and acylation with the residue of pyrene-1-yl-butanoic acid were achieved on support, using microwave irradiation to ensure full conversion. The UV-melting point of the duplex of the singly and doubly modified decamers with their fully complementary target sequence is 0.1-6.9 °C higher than that of the unmodified control duplex, depending on the salt concentration. This suggests that the aminomethyl linker may allow for the placing of a functional "payload" in the minor groove of DNA duplexes without disrupting the helix. Oligonucleotides thus endowed with functional modifications may become useful for biomedical applications.

Site-specific generation of deoxyribonolactone lesions in DNA oligonucleotides

(matrix presented) An efficient method for the site-specific generation of 2-deoxyribonolactone oxidative DNA damage lesions from a "photocaged" nucleoside analogue was developed. A nucleoside phosphoramidite bearing a C-1′ nitrobenzyl cyanohydrin was prepared and incorporated into DNA oligonucleotides using automated DNA synthesis. The caged analogue, which was stable in aqueous solution, was converted to the 2-deoxyribonolactone lesion by UV irradiation. DNA containing the caged analogue and the deoxyribonolactone site were characterized by electrospray mass spectrometry (ES-MS).