1415009-89-0Relevant academic research and scientific papers
A Modular Approach to the Total Synthesis of Tunicamycins
Li, Jiakun,Yu, Biao
, p. 6618 - 6621 (2015)
The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of N-acetyl-D-hexosamine-1-phosphate translocases and thus inhibit bacterial cell-wall synthesis and the N glycosylation of eukaryotic proteins. An efficient approach to the synthesis of this unique type of nucleoside antibiotics is now reported and features the assembly of five modules in a highly stereoselective and robust manner. A Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)-catalyzed O and N glycosylation, and final Nacylation were used as the key steps. The modular and stereoselective synthesis of tunicamycins features a Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)-catalyzed O and N glycosylation, and final N acylation as the key steps. These natural products are a unique type of nucleoside antibiotics with potent inhibitory activities against bacterial cell-wall synthesis and the N-glycosylation of eukaryotic proteins.
O-Aryl α,β-d-ribofuranosides: Synthesis & highly efficient biocatalytic separation of anomers and evaluation of their Src kinase inhibitory activity
Sharma, Raman K.,Singh, Sukhdev,Tiwari, Rakesh,Mandal, Deendayal,Olsen, Carl E.,Parmar, Virinder S.,Parang, Keykavous,Prasad, Ashok K.
, p. 6821 - 6830 (2013/01/15)
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 = 95.0 μM).
