Photolabile Protecting Groups for Nitroxide Spin Labels

被引：19

作者：

Seven, Ibrahim ^{[1
]}

Weinrich, Timo ^{[1
]}

Graenz, Markus ^{[2
]}

Gruenewald, Christian ^{[1
]}

Bruess, Silke ^{[1
]}

Krstic, Ivan ^{[2
]}

Prisner, Thomas F. ^{[2
]}

Heckel, Alexander ^{[1
]}

Goebel, Michael W. ^{[1
]}

机构：

[1] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany

[2] Goethe Univ Frankfurt, Inst Phys & Theoret Chem, D-60438 Frankfurt, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 19期

关键词：

Tetraethylisoindoline; EPR spectroscopy; Photochemistry; Phosphoramidites; TEMPO; Radicals; DNA; CHEMISTRY;

D O I：

10.1002/ejoc.201301692

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4037 / 4043

页数：7

共 35 条

[1] CONFORMATIONALLY RESTRICTED SPIN LABELED NUCLEOTIDES - A MODEL STUDY OF THE SYNTHESIS AND PROPERTIES OF THE 2',3'-O-SPIRO KETAL OF URIDINE AND 4-OXO-2,2,6,6-TETRAMETHYL-1-PIPERIDYLOXY [J].

ALESSI, DR ;

CORRIE, JET ;

FEENEY, J ;

TRAYER, IP ;

TRENTHAM, DR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2243-2247

[2] High-resolution distance mapping in rhodopsin reveals the pattern of helix movement due to activation [J].

Altenbach, Christian ;

Kusnetzow, Ana Karin ;

Ernst, Oliver P. ;

Hofmann, Klaus Peter ;

Hubbell, Wayne L. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2008, 105 (21) :7439-7444

[3] Site-directed spin-labeling of nucleotides and the use of in-cell EPR to determine long-range distances in a biologically relevant environment [J].

Azarkh, Mykhailo ;

Singh, Vijay ;

Oklre, Oliver ;

Seemann, Isabelle T. ;

Dietrich, Daniel R. ;

Hartig, Joerg S. ;

Drescher, Malte .

NATURE PROTOCOLS, 2013, 8 (01) :131-147

[4]

Barhate N., 2007, ANGEW CHEM, V119, P2709

[5] A nucleoside that contains a rigid nitroxide spin label: A fluorophore in disguise [J].

Barhate, Nivrutti ;

Cekan, Pavol ;

Massey, Archna P. ;

Sigurdsson, Snorri Th. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) :2655-2658

[6]

Bordignon E, 2007, BIOL MAGN RESON, V27, P129

[7]

Brieke C., 2012, ANGEW CHEM, V124, P8572

[8] Light-Controlled Tools [J].

Brieke, Clara ;

Rohrbach, Falk ;

Gottschalk, Alexander ;

Mayer, Guenter ;

Heckel, Alexander .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (34) :8446-8476

[9] Synthesis of spin-labeled riboswitch RNAs using convertible nucleosides and DNA-catalyzed RNA ligation [J].

Buettner, Lea ;

Seikowski, Jan ;

Wawrzyniak, Katarzyna ;

Ochmann, Anne ;

Hoebartner, Claudia .

BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (20) :6171-6180

[10] Identification of Single-Base Mismatches in Duplex DNA by EPR Spectroscopy [J].

Cekan, Pavol ;

Sigurdsson, Snorri Th. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (50) :18054-+

← 1 2 3 4 →