Sigmatropic rearrangement enables access to a highly stable spirocyclic nitroxide for protein spin labelling

Mateusz P.  Sowiński; Elena M. Mocanu; Hannah  Ruskin-Dodd; Aidan P. McKay; David B. Cordes; Janet E. Lovett; Marius  Haugland-Grange

doi:10.1039/D5CC00472A

Sigmatropic rearrangement enables access to a highly stable spirocyclic nitroxide for protein spin labelling

Mateusz P. Sowiński, Elena M. Mocanu, Hannah Ruskin-Dodd, Aidan P. McKay, David B. Cordes, Janet E. Lovett, Marius Haugland-Grange^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Spin labelling enables the study of biomolecules using electron paramagnetic resonance (EPR) spectroscopy. Here, we describe the synthesis of a cysteine-reactive spin label based on a spirocyclic pyrrolidinyl nitroxide containing an iodoacetamide moiety. The spin label was shown to be highly persistent under reducing conditions while maintaining excellent EPR relaxation parameters up to a temperature of 180 K. After successful double spin labelling of a calmodulin variant, interspin distances were measured by the EPR experiment double electron–electron resonance (DEER) at 120 K.

Original language	English
Number of pages	4
Journal	Chemical Communications
Volume	Advance Article
Early online date	27 Mar 2025
DOIs	https://doi.org/10.1039/D5CC00472A
Publication status	E-pub ahead of print - 27 Mar 2025

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Sowinski_2025_CC_Sigmatropic-rearrangement-stable-spirocyclic-nitroxide_CC
© 2025 The Author(s). This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (https://creativecommons.org/licenses/by/3.0/).
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Replication Data for: Sigmatropic rearrangement enables access to a highly stable spirocyclic nitroxide for protein spin labelling
Sowiński, M. P. (Creator), Mocanu, E. (Creator), Ruskin-Dodd, H. (Creator), Cordes, D. B. (Creator), Lovett, J. E. (Creator), Haugland-Grange, M. (Creator), Haugland-Grange, M. (Contributor) & Norway, U. T. A. U. O. (Contributor), DataverseNO, 2025
DOI: 10.18710/vc1h83
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title = "Sigmatropic rearrangement enables access to a highly stable spirocyclic nitroxide for protein spin labelling",

abstract = "Spin labelling enables the study of biomolecules using electron paramagnetic resonance (EPR) spectroscopy. Here, we describe the synthesis of a cysteine-reactive spin label based on a spirocyclic pyrrolidinyl nitroxide containing an iodoacetamide moiety. The spin label was shown to be highly persistent under reducing conditions while maintaining excellent EPR relaxation parameters up to a temperature of 180 K. After successful double spin labelling of a calmodulin variant, interspin distances were measured by the EPR experiment double electron–electron resonance (DEER) at 120 K.",

author = "Sowi{\'n}ski, {Mateusz P.} and Mocanu, {Elena M.} and Hannah Ruskin-Dodd and McKay, {Aidan P.} and Cordes, {David B.} and Lovett, {Janet E.} and Marius Haugland-Grange",

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month = mar,

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doi = "10.1039/D5CC00472A",

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T1 - Sigmatropic rearrangement enables access to a highly stable spirocyclic nitroxide for protein spin labelling

AU - Sowiński, Mateusz P.

AU - Mocanu, Elena M.

AU - Ruskin-Dodd, Hannah

AU - McKay, Aidan P.

AU - Cordes, David B.

AU - Lovett, Janet E.

AU - Haugland-Grange, Marius

PY - 2025/3/27

Y1 - 2025/3/27

N2 - Spin labelling enables the study of biomolecules using electron paramagnetic resonance (EPR) spectroscopy. Here, we describe the synthesis of a cysteine-reactive spin label based on a spirocyclic pyrrolidinyl nitroxide containing an iodoacetamide moiety. The spin label was shown to be highly persistent under reducing conditions while maintaining excellent EPR relaxation parameters up to a temperature of 180 K. After successful double spin labelling of a calmodulin variant, interspin distances were measured by the EPR experiment double electron–electron resonance (DEER) at 120 K.

AB - Spin labelling enables the study of biomolecules using electron paramagnetic resonance (EPR) spectroscopy. Here, we describe the synthesis of a cysteine-reactive spin label based on a spirocyclic pyrrolidinyl nitroxide containing an iodoacetamide moiety. The spin label was shown to be highly persistent under reducing conditions while maintaining excellent EPR relaxation parameters up to a temperature of 180 K. After successful double spin labelling of a calmodulin variant, interspin distances were measured by the EPR experiment double electron–electron resonance (DEER) at 120 K.

U2 - 10.1039/D5CC00472A

DO - 10.1039/D5CC00472A

M3 - Article

SN - 1359-7345

VL - Advance Article

JO - Chemical Communications

JF - Chemical Communications

ER -

Sigmatropic rearrangement enables access to a highly stable spirocyclic nitroxide for protein spin labelling

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Replication Data for: Sigmatropic rearrangement enables access to a highly stable spirocyclic nitroxide for protein spin labelling

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