O-Aryl α,β-d-ribofuranosides: Synthesis & highly efficient biocatalytic separation of anomers and evaluation of their Src kinase inhibitory activity
2012
Sharma, Raman K. | Sukhadewa Siṅgha, | Tiwari, Rakesh | Mandal, Deendayal | Olsen, Carl E. | Parmar, Virinder S. | Parang, Keykavous | Prasad, Ashok K.
A series of peracetylated O-aryl α,β-d-ribofuranosides have been synthesized and an efficient biocatalytic methodology has been developed for the separation of their anomers which was otherwise almost impossible by column chromatographic or other techniques. The incubation of 2,3,5-tri-O-acetyl-1-O-aryl-α,β-d-ribofuranoside with Lipozyme® TL IM immobilized on silica led to the selective deacetylation of only one acetoxy group, viz the C-5′-O-acetoxy group of the α-anomer over the other acetoxy groups derived from the two secondary hydroxyl groups present in the molecule and also over three acetoxy groups (derived from one primary and two secondary hydroxyls of the β-anomer). This methodology led to the easy synthesis of both, α- and β-anomers of O-aryl d-ribofuranosides. All the arylribofuranosides were screened for inhibition of Src kinase. 1-O-(3-Methoxyphenyl)-β-d-ribofuranoside exhibited the highest activity for inhibition of Src kinase (IC₅₀=95.0μM).
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