# Development of Bifunctional and Light Activated ReACT Bioconjugation Reagents via Nitrone Photoisomerization

> **NIH NIH F32** · UNIVERSITY OF CALIFORNIA BERKELEY · 2023 · $69,500

## Abstract

PROJECT SUMMARY/ABSTRACT
 The unique reactivity of oxaziridines towards methionine sidechains via N-transfer has been
successfully leveraged to make powerful bioconjugation reagents used by numerous research groups.
However, the utility of this reagent is limited by the difficulty of incorporating secondary reactive
handles and a narrow cargo scope due to the harsh synthesis conditions and sensitivity of oxaziridines.
Photoisomerization of nitrones provides a mild method of oxaziridine synthesis. This route to
oxaziridines allows for incorporation of cargo not accessible with current synthetic methods and
presents a powerful way of controlling oxaziridine reactivity using light. This proposal aims to elucidate
quantitative relationships between nitrone chemical structure and its ability to isomerize to
oxaziridines and the resulting oxaziridine bioconjugation reactivity. Nitrone photoisomerization will be
leveraged to synthesize bivalent reagents that incorporate other commonly used click handles. Finally,
the exquisite control over oxaziridine reactivity provided by the photoisomerization will be used to
uncage oxaziridine reactivity in situ for protein modifications. These studies will greatly expand the
utility of this valuable class of bioconjugation reagents.

## Key facts

- **NIH application ID:** 10555205
- **Project number:** 5F32GM142273-02
- **Recipient organization:** UNIVERSITY OF CALIFORNIA BERKELEY
- **Principal Investigator:** Kacper Skakuj
- **Activity code:** F32 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 2023
- **Award amount:** $69,500
- **Award type:** 5
- **Project period:** 2022-02-01 → 2024-01-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/10555205

## Citation

> US National Institutes of Health, RePORTER application 10555205, Development of Bifunctional and Light Activated ReACT Bioconjugation Reagents via Nitrone Photoisomerization (5F32GM142273-02). Retrieved via AI Analytics 2026-05-26 from https://api.ai-analytics.org/grant/nih/10555205. Licensed CC0.

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