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Merck

I4632

2-Iminobiotin

≥98% (TLC)

Synonym(s):

Guanidinobiotin, Hexahydro-2-imino-1H-thieno[3,4-d]imidazole-4-pentanoic acid

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About This Item

Empirical Formula (Hill Notation):
C10H17N3O2S
CAS Number:
13395-35-2
Molecular Weight:
243.33
UNSPSC Code:
12352203
NACRES:
NA.46
PubChem Substance ID:
24896060
MDL number:
MFCD00066150
Beilstein/REAXYS Number:
18952

Key Documents

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Product Name

2-Iminobiotin, ≥98% (TLC)

InChI

1S/C10H17N3O2S/c11-10-12-6-5-16-7(9(6)13-10)3-1-2-4-8(14)15/h6-7,9H,1-5H2,(H,14,15)(H3,11,12,13)/t6-,7-,9-/m0/s1

SMILES string

[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=N)N2

InChI key

WWVANQJRLPIHNS-ZKWXMUAHSA-N

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

solubility

1 M HCl: 50 mg/mL, clear, colorless

storage temp.

2-8°C

Quality Level

200

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Application

2-Iminobiotin has been used as a competitive inhibitor to bind to biotic binding sites on streptavidin in order to restore fluorescence signal.

Disclaimer

Unless otherwise stated in our catalog or other company documentation accompanying the product(s), our products are intended for research use only and are not to be used for any other purpose, which includes but is not limited to, unauthorized commercial uses, in vitro diagnostic uses, ex vivo or in vivo therapeutic uses or any type of consumption or application to humans or animals.

General description

2-Iminobiotin is a cyclic guanidino analog of biotin that has high affinity for avidin at high pH (>9) and low affinity at low pH (<6). The proteins that are iminobiotinylated are selectively contained within the avidin column at pH 9 to 11 and may be eluted at pH 4 or by the addition of biotin. This technique may be very useful in the study of cell surface proteins by labeling and selectively recovering the components that are periodate-sensitive from intact human erythrocyte surface. 2-Iminobiotin reversibly inhibits NOS (nitric oxide synthases) via its guanidino group. It inhibits NO biosynthesis and may be important to understand the binding-site interactions for this important class of enzymes. NOS oxidizes the guanidino-nitrogen of L-arginine to produce nitric oxide and L-citrulline.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

I4632-VAR: + I4632-BULK: + I4632-100MG: + I4632-25MG: + I4632-250MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000512522
0000512522
0000422253
0000422253
0000324192

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Tijen Utkan et al.
Pharmacology, biochemistry, and behavior, 101(4), 515-519 (2012-03-13)
The aim of this study was to compare the effects of both neuronal NOS (nNOS) and inducible NOS (iNOS) inhibitor 2-iminobiotin, with the more selective nNOS inhibitor N(ω)-propyl-L-arginine (NPLA) and selective inducible NOS (iNOS) inhibitor aminoguanidine, on emotional learning, working
Hiroyuki Inoue et al.
Biomacromolecules, 6(1), 27-29 (2005-01-11)
A layer-by-layer thin film composed of avidin and 2-iminobiotin-labeled poly(ethyleneimine) (ib-PEI) was prepared and their sensitivity to the environmental pH and biotin was studied. The avidin/ib-PEI multilayer assemblies were stable at pH 8-12, whereas the assemblies were decomposed at pH
Katsuhiko Sato et al.
Journal of colloid and interface science, 315(1), 396-399 (2007-07-17)
The effects of hydrogen peroxide on the electrochemical decomposition of layer-by-layer thin films composed of 2-iminobiotin-labeled poly(ethyleneimine) (ib-PEI) and avidin were studied. An ib-PEI/avidin thin film prepared on the surface of a platinum (Pt) film-coated quartz resonator was electrochemically decomposed
F K Athappilly et al.
Protein science : a publication of the Protein Society, 6(6), 1338-1342 (1997-06-01)
Streptavidin binds 2'-iminobiotin in a pH-dependent fashion--affinity decreases as the pH is lowered. This property makes the purification of compounds conjugated to streptavidin or immobiotin possible under mild conditions by affinity chromatography. In order to understand the molecular details of
Cacha Peeters-Scholte et al.
Experimental brain research, 156(1), 20-26 (2003-12-23)
Early detection of delayed cerebral energy failure may be important in the prevention of reperfusion injury of the brain after severe perinatal hypoxia-ischaemia (HI). This study investigated whether monitoring of the redox state of cytochrome aa(3) (Cytaa(3)) with near infrared
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