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An Unconventional Acid‐Labile Nucleobase Protection Concept for Guanosine Phosphoramidites in RNA Solid‐Phase Synthesis
Author(s) -
Jud Lukas,
Micura Ronald
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201605056
Subject(s) - guanosine , nucleobase , rna , combinatorial chemistry , chemistry , solid phase synthesis , nucleic acid , protecting group , biochemistry , organic chemistry , dna , gene , peptide , alkyl
We present an innovative O 6 ‐ tert ‐butyl/ N 2 ‐ tert ‐butyloxycarbonyl protection concept for guanosine (G) phosphoramidites. This concept is advantageous for 2′‐modified G building blocks because of very efficient synthetic access when compared with existing routes that usually employ O 6 ‐(4‐nitrophenyl)ethyl/ N 2 ‐acyl protection or that start from 2‐aminoadenosine involving enzymatic transformation into guanosine later on in the synthetic path. The new phosphoramidites are fully compatible with 2′‐ O ‐ t BDMS or TOM phosphoramidites in standard RNA solid‐phase synthesis and deprotection, and provide excellent quality of tailored RNAs for the growing range of applications in RNA biophysics, biochemistry, and biology.