110522-71-9Relevant articles and documents
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.
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.
