N-Succinimidyl S-acetylthioacetate
Properties
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Information about N-Succinimidyl S-acetylthioacetate / CAS 76931-93-6
N-succinimidyl S-acetylthioacetate (SATA) is a reagent used for cross-linking primary amines. It is a short-chain crosslinker, with a spacer arm of only 2.8 angstroms. SATA contains an N-hydroxysuccinimide (NHS) ester group. It works by adding a protected sulfhydryl group to the primary amine of proteins or peptides, such as lysine. The protected sulfhydryl group can be deprotected using hydroxylamine, which releases the NHS ester. The unprotected sulfhydryl group can then react with the sulfhydryl group on another molecule, forming a disulfide bond.
A recent study from the University of Oxford describes NHS esters as widely used tools for protein modification and bioconjugation, with applications including protein labeling and functionalization, the preparation of thiolated proteins using reagents such as SATA, and their use in drug-targeting conjugates and therapeutic biologics. In addition, modification with SATA may extend the shelf-life of proteins and peptides for long-term storage. Because SATA also reacts readily with antibodies, it is commonly used in immunoassays.
- Duncan, R. J. S., Weston, P. D., & Wrigglesworth, R. (1983). A new reagent which may be used to introduce sulfhydryl groups into proteins, and its use in the preparation of conjugates for immunoassay. Analytical Biochemistry, 132(1), 68–73. https://doi.org/10.1016/0003-2697(83)90426-8
- Mattson, G., Conklin, E., Desai, S., Nielander, G., Savage, M. D., & Morgensen, S. (1993). A practical approach to crosslinking. Molecular Biology Reports, 17(3), 167–183. https://doi.org/10.1007/BF00986726/METRICS
- Liu, W., Khan, A., Demyanenko, Y.et al.Thio-NHS esters are non-innocent protein acylating reagents. Nat Commun 16, 6028 (2025). https://doi.org/10.1038/s41467-025-60527-5