2-Iodacetamid

Bezeichnung:2-Iodacetamid

CAS-Nr144-48-9

Englisch Name:2-Iodoacetamide

CBNumberCB4760867

SummenformelC2H4INO

Molgewicht184.96

MOL-Datei144-48-9.mol

Synonyma

2-Iodacetamid

2-Iodacetamid physikalisch-chemischer Eigenschaften

Schmelzpunkt	92-95 °C(lit.)
Siedepunkt	297.1±23.0 °C(Predicted)
Dichte	2.1103 (estimate)
storage temp.	2-8°C
Löslichkeit	Soluble in water, dimethyl formamide and ethanol. Slightly soluble in methanol.
Aggregatzustand	crystalline
pka	15.16±0.40(Predicted)
Farbe	White to pale yellow or beige
Wasserlöslichkeit	H2O: 0.5M at 20°C, clear, colorless
Sensitive	Light Sensitive
BRN	1739080
Stabilität	Stable, but light sensitive. Incompatible with strong oxidizing agents, strong bases, reducing agents, acids.
InChIKey	PGLTVOMIXTUURA-UHFFFAOYSA-N
CAS Datenbank	144-48-9(CAS DataBase Reference)
NIST chemische Informationen	Alpha-iodo acetamide(144-48-9)
EPA chemische Informationen	2-Iodoacetamide (144-48-9)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25-42/43-43-36/37/38-53
S-Sätze:	22-36/37-45-37/39-26-24
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	AC4200000
F	8-10-21
TSCA	T
HazardClass	6.1
PackingGroup	III
HS Code	29241900

Gefahreninformationscode (GHS)

2-Iodoacetamide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R43:Sensibilisierung durch Hautkontakt möglich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S24:Berührung mit der Haut vermeiden.
Chemische Eigenschaften
White solid in amber, foil sealed microtubes. Soluble in hot water, easily soluble in ethanol.
Verwenden
2-Iodoacetamide is an alkylating reagent for cysteine residues in peptide sequencing. Its actions are similar to those of iodoacetate. By virtue of reaction with cysteine, it is an irreversible inhibitor of enzymes with cysteine at the active site. It reacts much more slowly with histidine residues, but that activity is responsible for inhibition of ribonuclease.
Application
Alkylating agent used in peptide mapping because it covalently binds with the thiols in cysteine to prevent disulfide bond formation 2-Iodoacetamide is used as an electrophile for covalent modification of nucleophilic residues on proteins such as cysteine, methionine and histidine. It is used to bind with thiol group of cysteine, thereby it protects the formation disulfide bonds. It is involved as an inhibitor of deubiquitinase enzymes (DUBs). Further, it acts as an alkylating sulfhydryl reagent.
Biologische Aktivität
Iodoacetamide acts as an alkylating reagent for cysteine residues in peptide sequencing. It is an irreversible inhibitor of enzymes with cysteine at the active site. It reacts much more slowly with histidine residues, but that activity is responsible for inhibiting ribonuclease.
Synthese
2-Iodoacetamide is synthesized by reacting chloroacetamide with sodium iodide. The chloroacetamide, anhydrous acetone, and anhydrous sodium iodide were refluxed on the bath for 15h. Cool to room temperature, filter out sodium chloride, recover acetone, pour into ice water of sodium bisulfate after a little cooling, and then neutralize to pH 6 with saturated sodium sulfate solution. Cool to crystallize and filter to obtain crude product. The crude product is recrystallized with water to obtain the finished product.
läuterung methode
Crystallise it from water or CCl4. It is used for tagging proteins. [Gurd Methods Enzymol 25 424 1972, Beilstein 2 IV 536.]
Preparation and handling
Alkylation Procedure
Iodoacetamide is unstable and light-sensitive. Prepare solutions immediately before use and perform alkylation in the dark. If iodoacetamide is present in limiting quantities and a slightly alkaline pH, cysteine modification will be the exclusive reaction. Excess iodoacetamide or non-buffered iodoacetamide reagent can also alkylate amines (lysine, N-termini), thioethers (methionine), imidazoles (histidine) and carboxylates (aspartate, glutamate).
1. Add 5 μl of 2% SDS and 45 μl of 200 mM ammonium bicarbonate (pH 8.0) to 20-100 μg of protein sample. Adjust volume to 100 μl with ultrapure water.
2. Add 5 μl of 200 mM Tris(2-carboxyethyl) phosphine hydrochloride (TCEP.HCl, Product No. 20490) and incubate sample at 55°C for 1 hour.
3. Immediately before use, dissolve one tube of iodoacetamide (9.3 mg) with 132 μl of 200 mM ammonium bicarbonate (pH 8.0) to make 375 mM iodoacetamide. Protect solution from light.
4. Add 5 μl of the 375 mM iodoacetamide to the sample and incubate for 30 minutes protected from light.
5. Proceed to proteolytic digestion before MS analysis or other processing.
Vorsichtsmaßnahmen
Store in a cool place. Light and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents.

2-Iodoacetamide Upstream-Materialien And Downstream Produkte

2-Iodacetamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

144-48-9, 2-Iodoacetamide Verwandte Suche:

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