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254940

Sigma-Aldrich

Methyl acetimidate hydrochloride

technical grade

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About This Item

Linear Formula:
CH3C(=NH)OCH3 · HCl
CAS Number:
14777-27-6
Molecular Weight:
109.55
Beilstein:
3671581
EC Number:
238-843-3
MDL number:
MFCD00012571
UNSPSC Code:
12352100
PubChem Substance ID:
24855275
NACRES:
NA.22

grade

technical grade

mp

105 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

Cl.COC(C)=N

InChI

1S/C3H7NO.ClH/c1-3(4)5-2;/h4H,1-2H3;1H

InChI key

WHYJXXISOUGFLJ-UHFFFAOYSA-N

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General description

Methyl acetimidate hydrochloride is an inhibitor of N-methylation of phosphatidylethanolamine. It also prevents the stimulation of purified cardiac sarcolemmal vesicles Ca2+-pump activities.

Application

Methyl acetimidate hydrochloride has been used in pre-crystallization chemical modification of lysine residues.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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K C Flanders et al.
Biochemistry, 21(18), 4244-4251 (1982-08-31)
N epsilon-Acetimidoglucagon to be used for semisynthesis was prepared by reacting glucagon with methyl acetimidate hydrochloride at pH 10.2, favoring acetimidation of the sole epsilon-amino group. N epsilon-Acetimidoglucagon was isolated from the crude acetimidoglucagon mixture by anion-exchange chromatography at pH
G J van Scharrenburg et al.
Biochemistry, 23(25), 6285-6294 (1984-12-04)
To study the structural importance of the NH2-terminal Ala1 residue of pancreatic phospholipase A2, several mutants were prepared by a stepwise semisynthetic approach. 13C NMR spectroscopy of 90%-enriched [[3-13C]Ala1] phospholipases A2 shows the pK values of the alpha-NH3+ groups of
L C Packman et al.
The Biochemical journal, 193(2), 525-539 (1981-02-01)
Two variants of chloramphenicol acetyltransferase which are specified by genes on plasmids found in Gram-negative bacteria were subjected to amidination with methyl acetimidate to determine the relative reactivity of surface lysine residues and to search for unreactive or "buried" amino
Michael R Shortreed et al.
Analytical chemistry, 78(18), 6398-6403 (2006-09-15)
A powerful approach to relative quantification by mass spectrometry is to employ labeling reagents that target specific functional groups in molecules of interest. A quantitative comparison of two or more samples may be readily accomplished by using a chemically identical
V Panagia et al.
Biochimica et biophysica acta, 856(2), 383-387 (1986-04-14)
Incubation of purified cardiac sarcolemmal vesicles (SL) in the presence of S-adenosyl-L-methionine, a methyl donor for the enzymatic N-methylation of phosphatidylethanolamine (PE), increased the Ca2+-stimulated ATPase and ATP-dependent Ca2+ accumulation activities. Quantitative analysis of the methylated phospholipids revealed that maximal
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