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Merck
CN

B2059

Biotin Polyethyleneoxide Iodoacetamide

Synonym(s):

Biotin PEO Iodoacetamide

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About This Item

Empirical Formula (Hill Notation):
C18H31IN4O5S
Molecular Weight:
542.43
NACRES:
NA.32
PubChem Substance ID:
24891627
UNSPSC Code:
12352119
MDL number:
MFCD04974830

Key Documents

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InChI key

LWGLKVINXNMNJX-UHFFFAOYSA-N

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)

description

Sulfhydryl specific, water soluble biotinylation reagent

form

powder

solubility

H2O: 10 mg/mL

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

  • 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.
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.

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.

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000493701
0000493701
0000486230
0000428107
0000428107

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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)
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.
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)
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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