N-hydroxysuccinimide esters undergo specific side reactions when exposed to competing nucleophiles.

the verdict

SUPPORTED

the evidence backs this

Recorded sources

2 sources for · 0 against

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N-hydroxysuccinimide (NHS) esters are well-known to undergo specific side reactions and competing nucleophilic attacks (such as O-derivatization or ring opening) alongside their primary reactions.

The analysis

The retrieved literature clearly demonstrates that NHS esters undergo unintended side reactions when exposed to competing nucleophiles (such as hydroxyl or other amino acid side chains), making the claim fully supported.

Evidence for · 2

Addressing NHS Chemistry: Efficient Quenching of Excess TMT Reagent and Reversing TMT Overlabeling in Proteomic Samples by Methylamine.

Recorded source metadata

Demyanenko Y, Sui X, Giltrap AM, Davis BG, Kuster B, Mohammed S. Addressing NHS Chemistry: Efficient Quenching of Excess TMT Reagent and Reversing TMT Overlabeling in Proteomic Samples by Methylamine.. 2025. https://doi.org/10.1016/j.mcpro.2025.100948

Paper [0] discusses how NHS esters react with competing nucleophiles such as serine, tyrosine, and threonine side chains to form unintended O-derivatives.

Source citation format

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More for · 1

Thio-NHS esters are non-innocent protein acylating reagents.

Recorded source metadata

Liu W, Khan A, Demyanenko Y, Mohammed S, Davis BG. Thio-NHS esters are non-innocent protein acylating reagents.. 2025. https://doi.org/10.1038/s41467-025-60527-5

Paper [1] demonstrates that NHS-ester derivatives undergo ring-opening and site-dependent side-reactions when exposed to competing nucleophilic environments.

Source citation format

The paper trail · every fact has a biography

first checked01 Aug 2026

judged → SUPPORTED · 7901 Aug 2026

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