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D8388

Sigma-Aldrich

Dimethyl pimelimidate dihydrochloride

powder

Synonym(s):
Dimethyl pimelinediimidate dihydrochloride, DMP
Linear Formula:
[CH3OC(=NH)CH2CH2]2CH2 · 2HCl
CAS Number:
Molecular Weight:
259.17
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

form

powder

Quality Level

reaction suitability

reagent type: cross-linking reagent

solubility

H2O: 10 mg/mL

storage temp.

−20°C

SMILES string

Cl.Cl.COC(=N)CCCCCC(=N)OC

InChI

1S/C9H18N2O2.2ClH/c1-12-8(10)6-4-3-5-7-9(11)13-2;;/h10-11H,3-7H2,1-2H3;2*1H

InChI key

LRHXBHUTQWIZTN-UHFFFAOYSA-N

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General description

Dimethyl pimelimidate dihydrochloride is a homobifunctional cross-linking reagent used in crosslinking, protein interaction and protein modification. It typically reacts with primary amines in the pH range 7.0-10.0 to form amidine bonds.

Application

Dimethyl pimelimidate dihydrochloride has been used to develop a technique for isolating Enterocytozoon bieneusi spores directly from human stool samples with a high degree of purity, which opens up new approaches for studying this parasite.

Caution

The reagent is readily hydrolyzed at neutral pH.

Other Notes

Note that the amidine linkage preserves original primary amine positive charge. Incorporates a seven atom linker.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

I Accoceberry et al.
Journal of clinical microbiology, 39(5), 1947-1951 (2001-04-28)
An original, reliable, and reproducible method for the purification of Enterocytozoon bieneusi spores from human stools is described. We recently reported the production of a species-specific monoclonal antibody (MAb) 6E52D9 immunoglobulin G2a (IgG2a) raised against the exospore of E. bieneusi
K Brew et al.
The Journal of biological chemistry, 250(4), 1434-1444 (1975-02-25)
The cross-linking of the two components of lactose synthetase, alpha-lactalbumin and a galactosyltransferase, with dimethylpimelimidate was examined. The extent of the cross-linking at pH 8.1 was found to be dependent upon the presence of substrates or inhibitors for the galactosyltransferase.
Semisynthetic fluorohydrolases prepared by chemical modification of ribonuclease.
David, E., et al.
Enz. Microbiol. Technol., 14, 885-892 (1992)
G B Karlsson et al.
Analytical biochemistry, 199(2), 219-222 (1991-12-01)
A method is described for the use of magnetic beads as a solid phase for the immunoprecipitation of labeled proteins. The anti-human transferrin receptor monoclonal antibody OKT-9 has been coupled to sheep anti-mouse IgG1-coated magnetic beads using the crosslinking agent
Kevin Michael Boehm et al.
BMC bioinformatics, 20(1), 7-7 (2019-01-07)
To further our understanding of immunopeptidomics, improved tools are needed to identify peptides presented by major histocompatibility complex class I (MHC-I). Many existing tools are limited by their reliance upon chemical affinity data, which is less biologically relevant than sampling

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