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914924

Sigma-Aldrich

3-[2-N-(Biotinyl)aminoethyldithio]propanoic acid

≥95%

Synonym(s):

3-((2-(5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethyl)disulfaneyl)propanoic acid, Biotin-SS-COOH, Cleavable biotin linker

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About This Item

Empirical Formula (Hill Notation):
C15H25N3O4S3
CAS Number:
104582-29-8
Molecular Weight:
407.57
MDL number:
MFCD04039425
UNSPSC Code:
12352106
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

mp

172-175 °C

storage temp.

−20°C

InChI

1S/C15H25N3O4S3/c19-12(16-6-8-25-24-7-5-13(20)21)4-2-1-3-11-14-10(9-23-11)17-15(22)18-14/h10-11,14H,1-9H2,(H,16,19)(H,20,21)(H2,17,18,22)/t10-,11-,14-/m0/s1

InChI key

LUKYYZVIDAWYMZ-MJVIPROJSA-N

Application

3-[2-N-(Biotinyl)aminoethyldithio]propanoic acid (Biotin-SS-COOH) is a cleavable, biotinylated crosslinkers. The linker can also be used for synthesis of chemical biology tools for labeling target proteins in biological experiments and assays. It possesses dual functionality: enrichment via the biotin and an embedded disulfide bridge for cleavage under reducing conditions.

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Other Notes

Uniformly Cationized Protein Efficiently Reaches the Cytosol of Mammalian Cells

A Mechanism-Based ICAT Strategy for Comparing Relative Expression and Activity Levels of Glycosidases in Biological Systems

Dissociation-independent selection of high-affinity anti-hapten phage antibodies using cleavable biotin-conjugated haptens

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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P Soumillion et al.
Applied biochemistry and biotechnology, 47(2-3), 175-189 (1994-05-01)
Despite recent progress, our understanding of enzymes remains limited: the prediction of the changes that should be introduced to alter their properties or catalytic activities in an expected direction remains difficult. An alternative to rational design is selection of mutants
M L Shimkus et al.
DNA (Mary Ann Liebert, Inc.), 5(3), 247-255 (1986-06-01)
Two biotin-labeled nucleotide analogs, Bio-4-dUTP and Bio-12-SS-dUPT, were synthesized by a modification of the procedure described by Langer et al. (1981). Deoxyuridine 5'-triphosphate was first mercurated at the 5-C and subsequently reacted with allylamine to form 5-(3-amino)allyldeoxyuridine 5'-triphosphate (AA-dUTP). AA-dUTP
Midori Futami et al.
Bioconjugate chemistry, 23(10), 2025-2031 (2012-09-20)
Protein cationization techniques are powerful protein transduction methods for mammalian cells. As we demonstrated previously, cationized proteins with limited conjugation to polyethylenimine have excellent ability to enter into cells by adsorption-mediated endocytosis [Futami, J., et al. (2005) J. Biosci. Bioeng.
Omid Hekmat et al.
Journal of proteome research, 7(8), 3282-3292 (2008-06-20)
An activity-based isotope-coded affinity tagging (AB-ICAT) strategy for proteome-wide quantitation of active retaining endoglycosidases has been developed. Two pairs of biotinylated, cleavable, AB-ICAT reagents (light H(8) and heavy D(8)) have been synthesized, one incorporating a recognition element for cellulases and

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