68200-72-6

Upstream product

• 39947-05-2 ((3aR,4R,6R,6aR)-6-(6-benzamido-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 98-88-4 benzoyl chloride 
• 362-75-4 2',3'-isopropylidene adenosine 
• 39947-04-1 N-6-benzoyl-2',3'-O-isopropylideneadenosine 

Downstream Products

• 57731-88-1 N⁶,N⁶-dibenzoyl-5'-deoxy-5'-iodo-2',3'-O-isopropylideneadenosine 
• 57731-96-1 C₂₀H₂₁N₅O₄ 
• 840476-05-3 (S)-2-Amino-4-[(3aS,4S,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-butyric acid 
• 40950-52-5 AdoHcy 
• 840476-09-7 (S)-4-[(3aS,4S,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 

Relevant academic research and scientific papers

Determinants of cofactor binding to DNA methyltransferases: Insights from a systematic series of structural variants of S-adenosylhomocysteine

S-Adenosylmethionine (AdoMet) is a commonly used cofactor, second only to ATP in the variety of reactions in which it participates. It is the methyl donor in the majority of methyl transfer reactions, including methylation of DNA, RNA, proteins and small molecules. Almost all structurally characterised methyltransferases share a conserved AdoMet-dependent methyltransferase fold, in which AdoMet is bound in the same orientation. Although potential interactions between the cofactor and methyltransferases have been inferred from crystal structures, there has not been a systematic study of the contributions of each functional group to binding. To explore the binding interaction we synthesised a series of seven analogues of the methyltransferase inhibitor S-adenosylhomocysteine (AdoHcy), each containing a single modification, and tested them for the ability to inhibit methylation by HhaI and HaeIII DNA methyltransferase. Comparison of the Ki values highlights the structural determinants for cofactor binding, and indicates which nucleoside and amino acid functional groups contribute significantly to AdoMet binding. An understanding of the binding of AdoHyc to methyltransferases will greatly assist the design of AdoMet inhibitors.

New aspects on the reactivity of radicals generated from 5′-deoxy-5′-iodoadenosine derivatives

Acrylonitrile can serve as a trap for a 5′-centered radical derived from adenosine affording the corresponding three carbon extended adenosine derivative 8 together with the known 5′,8-cyclization product 9.

Synthetic Approaches towards Nucleocidin and Selected Analogues; anti-HIV Activity in 4'-Fluorinated Nucleoside Derivatives

Nucleocidin 1 has been synthesised from the adenosine derivative 4 via the intermediacy of the dihalogeno compound 9.The latter compound showed slight but significant activity against HIV-infected cells while the isomer 10 and the monohalogeno compound 60 were inactive.Synthetic approaches towards other 4'-fluorinated nucleoside derivatives are also described.The epimeric 4'-fluorinated nucleosides 26 and 27 displayed similar activity against HIV-infected cells to that observed for the dihalogenated compound 9.