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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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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
Cody M Palumbo et al.
Chembiochem : a European journal of chemical biology, 21(11), 1633-1640 (2020-01-17)
Specific applications of CRISPR/Cas genome editing systems benefit from chemical modifications of the sgRNA. Herein we describe a versatile and efficient strategy for functionalization of the 3'-end of a sgRNA. An exemplary collection of six chemically modified sgRNAs was prepared
Kevin Y Lin et al.
ACS nano, 7(10), 9001-9009 (2013-09-11)
Thrombin is a serine protease and regulator of hemostasis that plays a critical role in the formation of obstructive blood clots, or thrombosis, that is a life-threatening condition associated with numerous diseases such as atherosclerosis and stroke. To detect thrombi
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
Jenny Tam et al.
International journal of molecular sciences, 21(9) (2020-05-01)
The use of fluorescent imaging probes that monitor the activity of proteases that experience an increase in expression and activity in tumors is well established. These probes can be conjugated to nanoparticles of iron oxide, creating a multimodal probe serving
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