2'-OMe-dmf-G-CE Phosphoramidite, a vital compound in the biomedicine industry, is leveraged for the crucial synthesis of oligonucleotides. These tiny yet potent molecules are widely utilized in treating an array of afflictions such as cancer, viral infections, and genetic disorders. Devised to heighten the steadfastness and efficacy of oligonucleotides, our product offers patients the potential for better therapeutic outcomes.
Reference Reading
1. Synthesis of 2'-Fluorinated Northern Methanocarbacyclic (2'-F-NMC) Nucleosides and Their Incorporation Into Oligonucleotides
Shigeo Matsuda, Pawan Kumar, Namrata D Erande, Masaaki Akabane-Nakata, Muthiah Manoharan Curr Protoc Nucleic Acid Chem . 2020 Mar;80(1):e103. doi: 10.1002/cpnc.103.
This article describes chemical synthesis of 2'-fluorinated Northern methanocarbacyclic (2'-F-NMC) nucleosides and phosphoramidites, based on a bicyclo[3.1.0]hexane scaffold bearing all four natural nucleobases (U, C, A, and G), and their incorporation into oligonucleotides by solid-supported synthesis. This synthesis starts from commercially available cyclopent-2-en-1-one to obtain the fluorinated carbocyclic pseudosugar intermediate (S.13), which can be converted to the uridine intermediate by condensation with isocyanate, followed by cyclization, and to adenine and guanine precursors by microwave-assisted reactions. All four 2'-F-NMC phosphoramidites are synthesized from S.13 in a convergent approach, and the monomers are used for synthesis of 2'-F-NMC-modified oligonucleotides. © 2020 by John Wiley & Sons, Inc. Basic Protocol 1: Preparation of fluorinated carbocyclic pseudosugar intermediate Basic Protocol 2: Preparation of 2'-F-NMC uridine and cytidine phosphoramidites Basic Protocol 3: Preparation of 2'-F-NMC adenosine phosphoramidite Basic Protocol 4: Preparation of 2'-F-NMC guanosine phosphoramidite Basic Protocol 5: Synthesis of oligonucleotides containing 2'-F-NMC.
2. Deoxyribonucleoside phosphoramidites
M K Chmielewski, S L Beaucage, A Grajkowski, L R Phillips, A Wilk Curr Protoc Nucleic Acid Chem . 2001 May;Chapter 2:Unit 2.7. doi: 10.1002/0471142700.nc0207s04.
The detailed preparation of deoxyribonucleoside phosphoramidites bearing a 4-[N-methyl-N-(2,2,2-trifluoroacetyl)amino]butyl group for P(III) protection is presented. The use of this group circumvents nucleobase alkylation during oligonucleotide deprotection. Two syntheses of phosphoramidites starting from either a phosphordichloridite precursor or a bis-(N,N-diisopropylamino)chlorophosphine intermediate are described for the phosphinylation of suitably protected deoxyribonucleosides.
3. On-demand synthesis of phosphoramidites
Alexander F Sandahl, Martin B Johansen, Kurt V Gothelf, Rikke A Hansen, Troels Skrydstrup, Thuy J D Nguyen Nat Commun . 2021 May 12;12(1):2760. doi: 10.1038/s41467-021-22945-z.
Automated chemical synthesis of oligonucleotides is of fundamental importance for the production of primers for the polymerase chain reaction (PCR), for oligonucleotide-based drugs, and for numerous other medical and biotechnological applications. The highly optimised automised chemical oligonucleotide synthesis relies upon phosphoramidites as the phosphate precursors and one of the drawbacks of this technology is the poor bench stability of phosphoramidites. Here, we report on the development of an on-demand flow synthesis of phosphoramidites from their corresponding alcohols, which is accomplished with short reaction times, near-quantitative yields and without the need of purification before being submitted directly to automated oligonucleotide synthesis. Sterically hindered as well as redox unstable phosphoramidites are synthesised using this methodology and the subsequent couplings are near-quantitative for all substrates. The vision for this technology is direct integration into DNA synthesisers thereby omitting manual synthesis and storage of phosphoramidites.
