Improved phosphoramidite building blocks for the synthesis of the simplified nucleic acid GNA.
An improved synthesis of glycol nucleic acids is reported using new phosphoramidite building blocks in which the exocyclic amino groups of adenine and guanine are protected as N-dimethylformamidines, whereas the amino group of cytosine is protected via an acetamide. Besides a more rapid synthesis with higher yields, these phosphoramidites allow the use of a quicker deprotection procedure in the subsequent solid-phase synthesis of GNA oligonucleotides.
Schlegel
Mark K
MK
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35032 Marburg, Germany.
Meggers
Eric
E
D000225:Adenine / Q000737:chemistry; D005559:Formamides / Q000737:chemistry; D006018:Glycols / Q000138:chemical synthesis*; D006147:Guanine / Q000737:chemistry; D009696:Nucleic Acids / Q000138:chemical synthesis*; D009841:Oligonucleotides / Q000138:chemical synthesis; D009943:Organophosphorus Compounds / Q000737:chemistry*
D005559:Formamides; D006018:Glycols; D009696:Nucleic Acids; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D006147:Guanine; D000225:Adenine