Site-directed spin labelling of proteins by Suzuki-Miyaura coupling via a genetically encoded aryliodide amino acid

被引：15

作者：

Kugele, Anandi ^{[1
,2
]}

Braun, Theresa Sophie ^{[1
,2
]}

Widder, Pia ^{[1
,2
]}

Williams, Lara ^{[1
,2
]}

Schmidt, Moritz Johannes ^{[1
,2
]}

Summerer, Daniel ^{[3
]}

Drescher, Malte ^{[1
,2
]}

机构：

[1] Univ Konstanz, Dept Chem, Univ Str 10, D-78457 Constance, Germany

[2] Univ Konstanz, Konstanz Res Sch Chem Biol KoRS CB, Univ Str 10, D-78457 Constance, Germany

[3] TU Dortmund Univ, Fac Chem & Chem Biol, Otto Hahn Str 4a, D-44227 Dortmund, Germany

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 13期

基金：

欧洲研究理事会;

关键词：

ESCHERICHIA-COLI; ALPHA-SYNUCLEIN; IN-VITRO; CHEMISTRY; DISEASE;

D O I：

10.1039/c8cc09325c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report site-directed protein spin labelling via Suzuki-Miyaura coupling of a nitroxide boronic acid label with the genetically encoded amino acid 4-iodo-L-phenylalanine. The resulting spin label bears a rigid biphenyl linkage with lower flexibility than spin label R1. It is suitable to obtain defined electron paramagnetic resonance distance distributions and to report protein-membrane interactions and conformational transitions of alpha-synuclein.

引用

页码：1923 / 1926

页数：4

共 42 条

[1] Site-directed spin labeling of a genetically encoded unnatural amino acid
Fleissner, Mark R.
Brustad, Eric M.
Kalai, Tamas
Altenbach, Christian
Cascio, Duilio
Peters, Francis B.
Hideg, Kalman
Peuker, Sebastian
Schultz, Peter G.
Hubbell, Wayne L.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2009, 106 (51) : 21637 - 21642
[2] Site-directed spin labeling of a genetically encoded unnatural amino acid (vol 106, 21637, 2009)
Fleissner, Mark R.
Brustad, Eric M.
Kalai, Tamas
Altenbach, Christian
Cascio, Duilio
Peters, Francis B.
Hideg, Kalman
Peuker, Sebastian
Schultz, Peter G.
Hubbell, Wayne L.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (12) : 5693 - 5693
[3] Applications of Genetically Encoded Unnatural Amino Acids for Protein Structure Mapping by Site-Directed Spin Labeling
Fleissner, Mark R.
Bridges, Michael D.
Kalai, Tamas
Axup, Jun Y.
Young, Douglas D.
Hideg, Kalman
Schultz, Peter G.
Hubbell, Wayne L.
BIOPHYSICAL JOURNAL, 2011, 100 (03) : 51 - 51
[4] Modification of indane-based unusual α-amino acid derivatives via the Suzuki-Miyaura coupling reaction
Kotha, S
Halder, S
Lahiri, KA
SYNTHESIS-STUTTGART, 2002, (03): : 339 - 342
[5] Total Synthesis of Bongkrekic Acid via Sequential Suzuki-Miyaura Coupling Reactions
Kanematsu, Makoto
Shindo, Mitsuru
Yoshida, Masahiro
Shishido, Kozo
SYNTHESIS-STUTTGART, 2009, (17): : 2893 - 2904
[6] Palladium-mediated site-selective Suzuki-Miyaura protein modification at genetically encoded aryl halides
Spicer, Christopher D.
Davis, Benjamin G.
CHEMICAL COMMUNICATIONS, 2011, 47 (06) : 1698 - 1700
[7] Site Selective Synthesis of Pentaarylpyridines via Multiple Suzuki-Miyaura Cross-Coupling Reactions
Reimann, Sebastian
Ehlers, Peter
Petrosyan, Andranik
Kohse, Stefanie
Spannenberg, Anke
Surkus, Annette E.
Ghochikyan, Tariel V.
Saghyan, Ashot S.
Lochbrunner, Stefan
Kuehn, Oliver
Ludwig, Ralf
Langer, Peter
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (09) : 1987 - 2008
[8] Site-Directed Spin Labelling of Sulfite Oxidase using Non Natural Amino Acids
Hahn, Aaron
Engelhard, Chistopher
Teutloff, Christian
Risse, Thomas
BIOPHYSICAL JOURNAL, 2014, 106 (02) : 192A - 192A
[9] Synthesis of 7-substituted indoles via directed ortho metallation and Suzuki-Miyaura cross-coupling.
Hartung, C
Fecher, A
Nolte, B
Snieckus, V
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U400 - U400
[10] Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki-Miyaura Cross-Coupling
Hoang, Gia L.
Yang, Zhao-Di
Smith, Sean M.
Pal, Rhitankar
Miska, Judy L.
Perez, Damaris E.
Pelter, Libbie S. W.
Zeng, Xiao Cheng
Takacs, James M.
ORGANIC LETTERS, 2015, 17 (04) : 940 - 943

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