110522-74-2Relevant articles and documents
Polymer supported carbodiimide strategy for the synthesis of N-acylated derivatives of deoxy- and ribo purinenucleosides using active esters
Tripathi, Snehlata,Misra, Krishna,Sanghvi, Yogesh S.
, p. 5045 - 5048 (2005)
A cost-effective synthetic strategy has been used for the selective protection of the exocyclic amino function of purine nucleosides. Instead of using the common protecting groups in their chloride or anhydride forms, the less expensive and nontoxic acidic form was chosen. The acids were first activated to an active ester form using DCC and further successfully used for N-acylation of purine nucleosides. The contamination of the N-acylated product with DCU was inconvenient and was avoided by use of polymer supported- carbodiimide that has the additional advantage of reusability.
Proofing of Photolithographic DNA Synthesis with 3′,5′-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites
Pirrung, Michael C.,Fallon, Lara,McGall, Glenn
, p. 241 - 246 (2007/10/03)
We have evaluated in a microchip format the photochemical solid-phase phosphoramidite DNA synthesis method we previously developed. A set of nucleoside building blocks with "easy-off" base protecting groups was prepared bearing photolabile 5′-O-dimethoxybenzoincarbonate (DMBOC) groups. Photolysis rates and cycle yields for these DMBOC-protected nucleotides covalently attached to planar, derivatized glass surfaces were determined by fluorescence imaging-based methods earlier developed by McGall et al. and described in detail elsewhere. Data were obtained for both 280/310 and 365/400 nm irradiation in a range of solvents. Deprotection of the DMBOC occurs fastest in a nonpolar medium or without solvent. The coupling efficiency of these amidites in the synthesis of homopolymers was determined to be in the range 80-97%, with purines generally showing lower efficiency than pyrimidines. These DMBOC-protected monomers were used to prepare a 4 × 4 array of 16 decanucleotides of the sequence 5′-AAXTAXCTAC-chip, where X = A, C, G, or T. The array was hybridized with a target deoxyeicosanucleotide of the sequence fluorescein-5′-CTGAACGGTAGCATCTTGAC. Surface fluorescence imaging demonstrated sequence-specific hybridization to this probe.
A simple method for N-acylation of adenosine and cytidine nucleosides using carboxylic acids activated in-situ with carbonyldiimidazole
Sinha,Sinha, Nanda D.,Davis,Davis, Peter,Schultze,Schultze, Lisa M.,Upadhya,Upadhya, Krishna
, p. 9277 - 9280 (2007/10/02)
Carboxylic acids are activated with 1,1'-carbonyldiimidazole in acetonitrile to form N-acylimidazoles which are then treated with per-trimethylsilyl ethers of nucleosides adenosine or cytidine at ambient temperature to generate exclusively N-acylated-Aden
Improvements in Oligodeoxyribonucleotide Synthesis using Phenoxyacetyl as Amino Protecting Group
Singh, Ramendra K.,Misra, K.
, p. 409 - 417 (2007/10/02)
Phenoxyacetyl group has been used successfully for the protection of exocyclic amino function on purine and pyrimidine bases of 2'-deoxynucleosides.In the case of 2'-deoxycytidine, quantitative selective protection has been achieved under controlled condi
FACILE REMOVAL OF NEW BASE PROTECTING GROUPS USEFUL IN OLIGONUCLEOTIDE SYNTHESIS
Schulhof, J. C.,Molko, D.,Teoule, R.
, p. 51 - 54 (2007/10/02)
New base protecting groups are proposed in place of benzoyl and isobutyryl groups.They are phenoxy acetyl for adenine and guanine and isobutyryl for cytosine.They are cleaved in aqueous ammonia in a shorter time at lower temperature.These easily removable groups are useful in the synthesis of modified oligonucleotides, containing fragile bases.
