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284262

Sigma-Aldrich

Iodoacetic anhydride

Synonym(s):

2-Iodoacetic anhydride, 2-Iodoacetyl 2-iodoacetate, Iodoacetic acid anhydride, Iodoacetyl anhydride

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About This Item

Linear Formula:
(ICH2CO)2O
CAS Number:
54907-61-8
Molecular Weight:
353.88
Beilstein:
1812140
MDL number:
MFCD00001080
UNSPSC Code:
12352100
PubChem Substance ID:
24857144
NACRES:
NA.22

form

solid

Quality Level

100

mp

47-49 °C (lit.)

solubility

chloroform: soluble 10%, clear to slightly hazy, yellow (pink or tan)

functional group

anhydride
ester
iodo

storage temp.

2-8°C

SMILES string

ICC(=O)OC(=O)CI

InChI

1S/C4H4I2O3/c5-1-3(7)9-4(8)2-6/h1-2H2

InChI key

RBNSZWOCWHGHMR-UHFFFAOYSA-N

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Application

Reagent used as linker for development of reagents used for differential protein quantitation via ion scanning

Reactant used for:
  • Sythesis of N-iodoacetyl glycosylamine derivatives and converting amino precursors to IA derivatives
  • Linking lysine residues to N-terminal α-amino groups of peptides
  • Capping amines and yielding a thiol reactive iodo-derivative
  • Iodoacetylation

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H314

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1A

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN7161
MKCH2071
MKCF3081
MKCC5307
MKBX9896V

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M W Reed et al.
Bioconjugate chemistry, 6(1), 101-108 (1995-01-01)
An endogenous nuclear enzyme, RNase H, is an important component in determining the efficacy of antisense oligodeoxynucleotides (ODNs). In an effort to improve the potency of antisense ODNs, conjugates with three different nuclear targeting signal peptides were prepared. These short
S J Wood et al.
International journal of peptide and protein research, 39(6), 533-539 (1992-06-01)
A novel method is described for the cyclization of peptides--or segments of polypeptides--which requires a free N-terminal alpha-amino group and a distal amino acid residue containing a nucleophilic side chain. The reaction is conducted in two steps, both in the
Rainer Hahn et al.
Journal of chromatography. A, 1217(40), 6203-6213 (2010-08-31)
To design a generic purification platform and to combine the advantages of fusion protein technology and matrix-assisted refolding, a peptide affinity medium was developed that binds inclusion body-derived N(pro) fusion proteins under chaotropic conditions. Proteins were expressed in Escherichia coli
S J Wood et al.
Bioconjugate chemistry, 3(5), 391-396 (1992-09-01)
We describe a new method for the transfer of carbohydrate moieties to polypeptides in which complex carbohydrate, in the form of glycosyl amino acid, is removed from an available glycoprotein, derivatized, and reacted with a polypeptide via an iodoacetylated alpha-amino
R Wetzel et al.
Bioconjugate chemistry, 1(2), 114-122 (1990-03-01)
A method is described for the highly selective modification of the alpha-amino groups at the N-termini of unprotected peptides to form stable, modified peptide intermediates which can be covalently coupled to other molecules or to a solid support. Acylation with

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