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B2059

Sigma-Aldrich

Biotin Polyethyleneoxide Iodoacetamide

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Synonym(s):
Biotin PEO Iodoacetamide
Empirical Formula (Hill Notation):
C18H31IN4O5S
Molecular Weight:
542.43
MDL number:
PubChem Substance ID:
NACRES:
NA.32

description

Sulfhydryl specific, water soluble biotinylation reagent

Quality Level

form

powder

solubility

H2O: 10 mg/mL

storage temp.

2-8°C

SMILES string

ICC(=O)NCCOCCOCCNC(=O)CCCCC1SCC2NC(=O)NC12

InChI

1S/C18H31IN4O5S/c19-11-16(25)21-6-8-28-10-9-27-7-5-20-15(24)4-2-1-3-14-17-13(12-29-14)22-18(26)23-17/h13-14,17H,1-12H2,(H,20,24)(H,21,25)(H2,22,23,26)

InChI key

LWGLKVINXNMNJX-UHFFFAOYSA-N

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F4024C5585760706
solubility

H2O: 10 mg/mL

solubility

-

solubility

-

solubility

-

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

description

Sulfhydryl specific, water soluble biotinylation reagent

description

-

description

-

description

-

General description

Biotin polyethyleneoxide (PEO) iodoacetamide is a sulfhydryl (thiol) specific biotinylation reagent.

Application

Biotin Polyethyleneoxide Iodoacetamide has been used as a thiol reactive reagent to demonstrate the presence of free thiols in capsid protein L1 of human papillomavirus 16. It has been used for biotinylation of proteins for ELISA (enzyme-linked immunosorbent assay) competition and pull down experiments.
  • Incorporates a 12 atom hydrophilic spacer.
  • Typically coupled to sulfhydryl groups at pH 7.5 - 8.5
  • Especially useful for cysteine labeling in many proteomics type applications such as peptide mapping and mass spectrometry.

Biochem/physiol Actions

Biotin polyethyleneoxide (PEO) iodoacetamide group reacts specifically with reduced thiols at pH 7.5 - 8.5. Peptides and small molecules containing thiol groups may also be labeled using this reagent. The biotin PEO iodoacetamide enables tagging of cysteine residues and conjugation to sulfhydryls in proteins making it useful in proteomics, peptide mapping, phosphopeptide analysis, and mass spectrometry.

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Pictograms

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Signal Word

Warning

Hazard Statements

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

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Thiol-reactive reagents inhibits intracellular trafficking of human papillomavirus type 16 pseudovirions by binding to cysteine residues of major capsid protein L1.
Ishii Y, et al.
Virology Journal, 4, 110-110 (2007)
Beta-peptides with improved affinity for hDM2 and hDMX.
Harker EA, et al.
Bioorganic & Medicinal Chemistry, 17, 2038-2046 (2009)
A thermodynamic model for Nap1-histone interactions.
Andrews AJ, et al.
The Journal of Biological Chemistry, 283, 32412-32418 (2008)
Eric A Berg et al.
Cold Spring Harbor protocols, 2020(1), pdb-pdb (2020-01-04)
There are several techniques for biotinylating antibodies, from the most basic (using NHS-ester biotin to label primary amines) to more complex experiments (modifying sulfhydryls and carbohydrates). Biotinylation of free sulfhydryls, described here, can be effectively mediated using haloacetyl biotin derivatives.
Barbara Roman et al.
Journal of molecular and cellular cardiology, 144, 87-96 (2020-05-23)
In cardiomyocytes, there is microRNA (miR) in the mitochondria that originates from the nuclear genome and matures in the cytoplasm before translocating into the mitochondria. Overexpression of one such miR, miR-181c, can lead to heart failure by stimulating reactive oxygen

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