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I9760

Sigma-Aldrich

Iodoacetic acid N-hydroxysuccinimide ester

for peptide synthesis

Synonym(s):

N-Hydroxysuccinimide iodoacetate, N-Iodoacetoxysuccinimide

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About This Item

Empirical Formula (Hill Notation):
C6H6INO4
CAS Number:
39028-27-8
Molecular Weight:
283.02
MDL number:
MFCD00058451
UNSPSC Code:
12352005
PubChem Substance ID:
57654310
NACRES:
NA.22

product name

Iodoacetic acid N-hydroxysuccinimide ester, powder

form

powder

reaction suitability

reagent type: cross-linking reagent

solubility

DMF: 50 mg/mL

application(s)

peptide synthesis

functional group

NHS ester

storage temp.

−20°C

SMILES string

O=C(N1OC(CI)=O)CCC1=O

InChI

1S/C6H6INO4/c7-3-6(11)12-8-4(9)1-2-5(8)10/h1-3H2

InChI key

VRDGQQTWSGDXCU-UHFFFAOYSA-N

Application

A heterobifunctional cross-linking reagent with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5) Second coupling specific for molecules containing free sulfydryl by thioether linkage buffered at pH 7.5 (7.0-8.0). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Provides a 2-atom linker.

Caution

The iodoacetyl group is light sensitive.

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

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kevin Y Lin et al.
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G Houen et al.
Journal of immunological methods, 181(2), 187-200 (1995-04-26)
Two methods for the preactivation of proteins and conjugation of peptides to proteins under mild conditions are presented. Preactivation of proteins with divinylsulfone (DVS) permits peptide conjugation through either amino, hydroxyl or sulphydryl groups depending on the coupling pH used
Julian P Sefrin et al.
Frontiers in immunology, 10, 1962-1962 (2019-09-27)
Anti-tumor immunity is limited by a number of factors including the lack of fully activated T-cells, insufficient antigenic stimulation and the immune-suppressive tumor microenvironment. We addressed these hurdles by developing a novel class of immunoconjugates, Antibody-Targeted Pathogen-derived Peptides (ATPPs), which
E S Rector et al.
Journal of immunological methods, 24(3-4), 321-336 (1978-01-01)
A novel procedure for the synthesis of well-defined protein-protein conjugates is described using ovalbumin (OA) and IgG as test proteins. This procedure involves the highly selective and rapid reaction of alkyl halide and sulfhydryl groups, which have been grafted, respectively
Elena V Piletska et al.
Journal of molecular recognition : JMR, 33(4), e2824-e2824 (2019-11-20)
A library of 17 nanoparticles made of acrylate and methacrylate copolymers is prepared, characterized, and screened against six epitopes of adeno-associated viruses (AAV)-neutralizing antibodies to assess their affinity and specificity. Peptide epitopes are immobilized onto the surface of glass beads
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