SMCC crosslinker Chemical Properties

Melting point:

180-182 °C (lit.)

Boiling point:

501.7±42.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

chloroform: 50 mg/mL

form 

powder

pka

-2.24±0.20(Predicted)

color 

White to Off-White

Sensitive 

Moisture & Light Sensitive

BRN 

1555271

InChI

InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2

InChIKey

JJAHTWIKCUJRDK-UHFFFAOYSA-N

SMILES

C1(C(ON2C(=O)CCC2=O)=O)CCC(CN2C(=O)C=CC2=O)CC1

CAS DataBase Reference

64987-85-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-60-37

WGK Germany 

3

F 

10-21

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich

SMCC crosslinker Usage And Synthesis

Description

SMCC crosslinker is a hetero-bifunctional crosslinker that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. SMCC crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, and then can be added to an aqueous crosslinking reaction. SMCC crosslinking reagent is permeable across the lipid bilayer of the cell membrane and can be used to crosslink intracellular proteins and peptides.

Chemical Properties

White Crystalline Solid

Uses

A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(abTaIII)2 fragments to l-B-galactosidase. Conjugates hIgG to alkaline phosphatase.Spacer Arm: 11.6 Angstroms.

Definition

ChEBI: Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate is an N-hydroxysuccinimide ester derived from 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid. It is a member of maleimides and a N-hydroxysuccinimide ester.

General Description

4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester (SMCC) is a heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. It is typically coupled initially to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). SMCC contains nine atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.

Chemical Reactivity

Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a non-cleavable and membrane permeable crosslinker. It contains an amine-reactive N -hydroxysuccinimide (NHS ester) and a sulfhydryl-reactive maleimide group. NHS esters react with primary amines at pH 7-9 to form stable amide bonds. Maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. The maleimide groups of SMCC and Sulfo-SMCC and are unusually stable up to pH 7.5 because of the cyclohexane bridge in the spacer arm.

SMCC crosslinker(64987-85-5)Related Product Information

• Bismaleimide
• N-Chlorosuccinimide
• Succinimide
• Methyl acrylate
• RESMETHRIN
• Tris(trimethylsilyl)phosphate
• Cyclohexane
• Cyclohexanecarboxylic acid
• O-Phthalimide
• Alendronic acid
• Phosphonic acid, P,P'-[4-[[[4-[(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl]cyclohexyl]carbonyl]amino]-1-hydroxybutylidene]bis-
• Tranexamic Acid
• 6-Aminocaproic acid
• N-ETHYL ACRYLAMIDE
• DIALIFOS
• Maleimide
• Methylcyclohexane
• Acetohydroxamic acid