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
Pages (from-to)	6755-6758
Number of pages	4
Journal	Chemical Communications
Volume	61
Issue number	37
Early online date	27 Mar 2025
DOIs	https://doi.org/10.1039/D5CC00472A
Publication status	Published - 7 May 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/).
Final published version, 1.03 MBLicence: CC BY

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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
Dataset

DEER measurements of calmodulin: novel spin labels and structural insights
Mocanu, E. M. (Author), Lovett, J. (Supervisor), 3 Jul 2026
Student thesis: Doctoral Thesis (PhD)

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@article{a5ef7919476e42e9a0d7a683aa58a27e,

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",

year = "2025",

month = may,

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doi = "10.1039/D5CC00472A",

language = "English",

volume = "61",

pages = "6755--6758",

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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 - 2025/5/7

Y1 - 2025/5/7

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 - 61

SP - 6755

EP - 6758

JO - Chemical Communications

JF - Chemical Communications

IS - 37

ER -

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

Abstract

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

Student theses

DEER measurements of calmodulin: novel spin labels and structural insights

Cite this