221258-69-1

Upstream product

• 133320-04-4 (1S,2R)-2-(hydroxymethyl)cyclopentan-1-ol 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 178456-34-3 (1R,2R)-2-acetoxy-1-(acetoxymethyl)-3-cyclopentene 
• 542-92-7 cyclopenta-1,3-diene 
• 221258-63-5 (1R,2R)-2-(4,4'-dimethoxytrityloxymethyl)-cyclopentanol 
• 221258-61-3 (1R,2R)-2-(acetoxymethyl)-cyclopentanyl acetate 
• 133320-05-5 (1R,2R)-2-(hydroxymethyl)cyclopentan-1-ol 
• 110567-21-0 (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene 
• 221258-66-8 (1S,2R)-2-(4,4'-dimethoxytrityloxymethyl)-cyclopentanyl p-nitrobenzoate 

Relevant academic research and scientific papers

Properties of oligonucleotide with phenyl-substituted carbocyclic nucleoside analogs for the formation of duplex and triplex DNA

(1S,3S,4R)-1-Phenyl-1-thymidyl-3-hydroxy-4-hydroxymethylcyclopentane (10) and their analogs were synthesized, incorporated into the oligodeoxynucleotides, and their properties were evaluated for the formation of duplex and triplex DNA. The known chiral cyclopentanone derivative was converted into the corresponding ketimine sulfonamide derivative, which was subjected to a stereoselective PhLi addition. The formed sulfonamide was hydrolyzed to afford the primary amino group, on which the thymine moiety was built. The benzyl protecting groups were removed to form the nucleoside analog having a phenyl group and the thymine unit at the 1 position of a carbocyclic skeleton (10). In the estimation of the oligodeoxynucleotides incorporating 10 for duplex and triplex formation, the carbocyclic nucleoside analog 10 did not show the stabilizing effect for duplex formation; on the other hand, it stabilized the triplex. Therefore, the skeleton of the phenyl-substituted carbocyclic nucleoside analog 10 may be a platform for the formation of stable triplex DNA.

Synthesis and analysis of oligonucleotides containing abasic site analogues

(Figure Presented) DNA damage results in the formation of abasic sites from the formal hydrolysis of the glycosidic bond (AP) and several oxidized abasic lesions. Previous studies on AP sites revealed that DNA polymerases preferentially incorporated dA op

Inhibition of (cytosine C5)-methyltransferase by oligonucleotides containing flexible (cyclopentane) and conformationally constrained (bicyclo[3.1.0]hexane) abasic sites

Pseudorotationally locked sugar analogues based on bicyclo[3.1.0]-hexane templates were placed in DNA duplexes as abasic target sites in the M.HhaI recognition sequence. The binding affinity of the enzyme increases when the abasic site is constrained to t

Synthesis of an enantiomerically pure carbocyclic DNA abasic site analogue

A short synthetic route to an appropriately derivatized carbocyclic analogue of a basic site residues of DNA is proposed.