Methoxyoxalamido chemistry in the synthesis of novel amino linker and spacer phosphoramidites: a robust means for stability, structural versatility, and optimal tether length.
We have developed a general route to the synthesis of novel amino linker and spacer phosphoramidites utilizing methoxyoxalamido (MOX) chemistry. The synthesis makes use of readily available and inexpensive primary aliphatic amino alcohols and diamines to produce a rich and diverse variety of phosphoramidites. Among these are monomers with exceptionally long (up to 56 atoms in length) amphipathic tethering arms. The chemistry bestows exceptional control over the physical characteristics within the tethers through the selection of appropriate building blocks. Furthermore, MOX chemistry enables fairly rapid assembly of these discrete-length tethers in a modular fashion. All novel phosphoramidites were successfully used in automated syntheses of 5'-modified oligonucleotides.
Morocho
A Michael
AM
Fidelity Systems Inc., 7961 Cessna Avenue, Gaithersburg, MD 20879, USA.
Karamyshev
Valeri N
VN
Polushin
Nikolai N
NN
D004355:Drug Stability; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010072:Oxamic Acid / Q000031:analogs & derivatives / Q000737:chemistry*
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D010072:Oxamic Acid