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Succinimidyl 6-(4,4´-azipentanamido)hexanoate [NHS-LC-Diazirine]

Succinimidyl 6-(4,4´-azipentanamido)hexanoate, also known as NHS-LC-Diazirine, represents a significant breakthrough in crosslinking technology. This compound belongs to a novel class of heterobifunctional crosslinkers (e.g., SDA, LC-SDA, and SDAD) that have effectively combined two established chemical modalities, N-hydroxysuccinimide (NHS) ester chemistry and diazirine-based photoreactions. At pH 7 to 9, the NHS ester groups form covalent amide bonds with primary amines on one protein, while the diazirine (azipentanoate) moieties exhibit efficient reactivity towards amino acid side chains or peptide backbones on another protein within the prescribed spacer arm distance, once activated by long-wave UV light (330-370 nm). LC-SDA's two-step chemical crosslinking process can be easily activated using conventional laboratory UV lamps, streamlining experimental protocols. Furthermore, LC-SDA crosslinkers demonstrate excellent photostability even under standard laboratory lighting conditions, eliminating the need for a light-restricted environment. Given that NHS-ester diazirine derivatives lack a charged group and are membrane-permeable, they are ideally suited for in vivo intracellular and intramembrane conjugations and investigating protein-protein interactions.

References

View all 38 references: Citation Explorer
Three-Dimensional Reconstruction of the Hepatitis C Virus Envelope Glycoprotein E1E2 Heterodimer by Electron Microscopic Analysis.
Authors: Kanai, Tapan and Hu, Zongyi and Yang, Renbin and Wu, Weimin and Wang, Ziqiu and Ma, Christopher D and Sanchez-Meza, Jaime and Law, Mansun and Houghton, Michael and Law, John Lokman and Logan, Michael and de Val, Natalia and Liang, T Jake
Journal: Journal of virology (2023): e0178822
Synthesis, Enzymatic Peptide Incorporation, and Applications of Diazirine-Containing Isoprenoid Diphosphate Analogues.
Authors: Justyna, Katarzyna and Das, Riki and Lorimer, Ellen L and Hu, Jiayue and Pedersen, Jodi S and Sprague-Getsy, Andrea M and Schey, Garrett L and Sieburg, Michelle A and Koehn, Olivia J and Wang, Yen-Chih and Chen, Yong-Xiang and Hougland, James L and Williams, Carol L and Distefano, Mark D
Journal: Organic letters (2023): 6767-6772
A photo-cross-linking GlcNAc analog enables covalent capture of N-linked glycoprotein-binding partners on the cell surface.
Authors: Wu, Han and Shajahan, Asif and Yang, Jeong-Yeh and Capota, Emanuela and Wands, Amberlyn M and Arthur, Connie M and Stowell, Sean R and Moremen, Kelley W and Azadi, Parastoo and Kohler, Jennifer J
Journal: Cell chemical biology (2022): 84-97.e8
Reactive intermediates for interactome mapping.
Authors: Seath, Ciaran P and Trowbridge, Aaron D and Muir, Tom W and MacMillan, David W C
Journal: Chemical Society reviews (2021): 2911-2926
Comparison of photoactivatable crosslinkers for in-gel immunoassays.
Authors: Tan, Kristine Y and Desai, Surbhi and Raja, Erum and Etienne, Chris and Webb, Brian and Herr, Amy E
Journal: The Analyst (2021): 6621-6630
Page updated on April 25, 2025

Ordering information

Price
Unit size
5 x 1 mg
25 mg
Catalog Number
3900239003
Quantity
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Physical properties

Molecular weight

338.36

Solvent

DMSO

Storage, safety and handling

H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22

Storage

Refrigerated (2-8 °C); Desiccated
UNSPSC12171501

CAS

1435895-19-4
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