Chemical Name: N-[(4-Maleimidomethyl)cyclohexylcarbonyloxy]sulfosuccinimide,sodium salt
CAS: 92921-24-9

Appearance: White to almost white powder
Purity: ≥90.0% (HPLC)
MW: 436.37, C16H17N2NaO9S

Storage Condition: -20ºC
Shipping Condition: with blue ice


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Product Description
Sulfo-SMCC is a bifunctional reagent contaning a maleimide group and an N- hydroxysuccinimide active ester on different ends of the molecule. Maleimide group react with SH group, but N- hydroxysuccinimide active ester reacts specifically with amino groups. At pH above neutral, active ester group to form a stable amide bond with an amino group. On the other hand, maleimide groups can be reacted selectively with respect to the thiol group under the conditions of pH6-7. Further, Sulfo-SMCC having a cyclohexane structure linker site is characterized as compared with the same type of crosslinking agent having an aromatic ring in the linker portion, the stability of the maleimide groups that increase. Since the active ester group having a sulfonic acid group is introduced, it is possible to carry out the labeling reaction without using an organic solvent such as DMSO or DMF.

Hetero-bifunctional Reagents

Product NameCodeLength (Å)
1) S. Hashida, M. Imagawa, S. Inoue, K.-H. Ruan and E. Ishikawa, “MoreUseful Maleimide Compounds for the Conjugation of Fab’ to HorseradishPeroxidase Through Thiol Groups in the Hinge”, J. Appl. Biochem., 1984,6, 56.
2) O. Prat, E. Lopez and G. Mathis, “Europium(III) Cryptate: A FluorescentLabel for the Detection of DNA Hybrids on Solid Support”, Anal. Biochem.,1991, 195(2), 283.
3) O. Siiman, A. Burshteyn, J. A. Maples and J. K. Whitesell,”Tris(3-mercaptopropyl)-N-glycylaminomethane as a New Linker to BridgeAntibody with Metal Particles for Biological Cell Separations”, BioconjugateChem., 2000, 11(4), 549.
4) T. P. Thomas, A. K. Patri, A. Myc, M. T. Myaing, J. Y. Ye, T. B. Norris andJ. R. Baker Jr., “In Vitro Targeting of Synthesized Antibody-conjugatedDendrimer Nanoparticles”, Biomacromolecules, 2004, 5(6),2269.
5) V. Gauvreau, G. Laroche, “Micropattern Printing of Adhesion, Spreading,and Migration Peptides on Poly(tetrafluoroethylene) Films to PromoteEndothelialization”, Bioconjugate Chem., 2005, 16(5),1088.

Related Categories
Surface Chemistry

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