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Photolabile Protecting Groups for Nitroxide Spin Labels
Author(s) -
Seven Ibrahim,
Weinrich Timo,
Gränz Markus,
Grünewald Christian,
Brüß Silke,
Krstić Ivan,
Prisner Thomas F.,
Heckel Alexander,
Göbel Michael W.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301692
Subject(s) - chemistry , nitroxide mediated radical polymerization , phosphoramidite , yield (engineering) , dna , combinatorial chemistry , spin label , alkylation , spin (aerodynamics) , rna , site directed spin labeling , protecting group , organic chemistry , oligonucleotide , biochemistry , catalysis , polymer , polymerization , materials science , alkyl , radical polymerization , membrane , engineering , metallurgy , gene , aerospace engineering
Nitroxide spin labels can be protected against critical conditions of DNA/RNA or peptide synthesis by reduction and alkylation with light‐sensitive groups such as nitrobenzyl‐ or aminocoumarins. High chemical stability qualifies tetraethylisoindoline 5 and, with some restrictions, (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxy (TEMPO) precursor 4 as building blocks for spin‐labeled biopolymers. The yield of recovered nitroxides (80–95 %) is sufficient for PELDOR experiments. A protected TEMPO phosphoramidite was successfully used to synthesize a short spin‐labeled DNA with high yield and purity.