Synthesis of RNA containing 5-hydroxymethyl-, 5-formyl-, and 5-carboxycytidine

Michaelides, Iacovos N.; Tago, Nobuhiro; Viverge, Bastien and Carell, Thomas (14. September 2017): Synthesis of RNA containing 5-hydroxymethyl-, 5-formyl-, and 5-carboxycytidine. In: Chemistry-A European Journal, Vol. 23, No. 63: pp. 15894-15898

Abstract

5-Hydroxymethyl-, 5-formyl-, and 5-carboxycytidine are new epigenetic bases (hmdC, fdC, cadC) that were recently discovered in the DNA of higher eukaryotes. The same bases (hmC, fC and caC) have now also been detected in mammalian RNA with a high abundance in mRNA. While for the DNA bases phosphoramidites (PAs) are available that allow the synthesis of xdC-containing oligonucleotides for deeper biological studies, the corresponding silyl protected RNA PAs for fC and caC have not yet been disclosed. Here we report novel RNA PAs for hmC, fC and caC that can be used in routine RNA synthesis. The new building blocks are compatible with the canonical PAs and also with themselves, which enables even the synthesis of RNA strands containing all three of these bases. The study will pave the way for detailed physical, biochemical and biological studies to unravel the function of these non-canonical modifications in RNA.

• Item Type: Journal article
• EU Funded Grant Agreement Number: 642023
• EU Projects: Horizon 2020 > Marie Skłodowska Curie Actions > Marie Skłodowska-Curie Innovative Training Networks > 642023: ClickGene - Click Chemistry for Future Gene Therapies to Benefit Citizens, Researchers and Industry
• Form of publication: Postprint
• Keywords: RNA epigenetics; mRNA modifications; oligonucleotides; phosphoramidites; cytidine modifications
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Research Centers: Center for Integrated Protein Science Munich (CIPSM)
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0947-6539
• Language: English