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Merck
CN

M6035

4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt

powder

Synonym(s):

Sulfo-SMCC

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About This Item

Empirical Formula (Hill Notation):
C16H17N2NaO9S
CAS Number:
92921-24-9
Molecular Weight:
436.37
NACRES:
NA.47
PubChem Substance ID:
24897071
UNSPSC Code:
12171500
MDL number:
MFCD00054978

Key Documents

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Product Name

4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt, powder

InChI

1S/C16H18N2O9S.Na/c19-12-5-6-13(20)17(12)8-9-1-3-10(4-2-9)16(23)27-18-14(21)7-11(15(18)22)28(24,25)26;/h5-6,9-11H,1-4,7-8H2,(H,24,25,26);/q;+1/p-1

SMILES string

O=C(N1CC2CCC(C(ON3C(CC(S(=O)(O[Na])=O)C3=O)=O)=O)CC2)C=CC1=O

InChI key

VUFNRPJNRFOTGK-UHFFFAOYSA-M

form

powder

reaction suitability

reagent type: linker

technique(s)

titration: suitable

color

white to light brown

solubility

H2O: 2.5 mg/mL
DMF: soluble

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

2-8°C

Quality Level

300

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Analysis Note

May contain dimethylformamide.

Biochem/physiol Actions

4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt is known to introduce a well-defined number of maleimide groups into the protein which confers them a long shelf-life at low temperatures and can be further labeled with Fluorine-18[18F].

General description

4-(N-Maleimidomethyl)cyclohexane-1-carboxylic acid 3-sulfo-N-hydroxysuccinimide ester sodium salt (sulfoSMCC) is a heterobifunctional protein/peptide cross-linker and a suitable cross-coupling reagent.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF3455V
WXBF3025V
WXBF4082V
WXBF0912V
WXBF2308V

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Marc Rigau et al.
Science (New York, N.Y.), 367(6478) (2020-01-11)
Gamma delta (γδ) T cells are essential to protective immunity. In humans, most γδ T cells express Vγ9Vδ2+ T cell receptors (TCRs) that respond to phosphoantigens (pAgs) produced by cellular pathogens and overexpressed by cancers. However, the molecular targets recognized
Renshaw S
Immunohistochemistry and Immunocytochemistry: Essential Methods (2017)
Robert K Strother et al.
Journal of immunology (Baltimore, Md. : 1950), 197(11), 4301-4311 (2016-11-01)
Patients surviving acute stages of sepsis often display impaired adaptive-immune responses. Using the cecal ligation and puncture model, we demonstrated that sepsis leads to substantial and long-lasting changes in the naive CD8 T cell repertoire, affecting the capacity of the
Cláudia S M Fernandes et al.
Biotechnology journal, 11(12), 1513-1524 (2016-08-06)
Retroviral particles are expensive to manufacture, mostly due to the downstream processing steps which result in low recoveries (≈30%) and concentration factors. In this work, a dodecapeptide phage-display library was panned against retrovirus like particles expressing the envelope protein Ampho4070A
Protein labeling with the labeling precursor [(18)F]SiFA-SH for positron emission tomography.
Wangler B
Nature Protocols, 7, 1964-1964 (2012)
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