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B4531

Sigma-Aldrich

Biotin disulfide N-hydroxysuccinimide ester

>98%, powder

Synonym(s):

(2-[Biotinamido]ethylamido)-3,3′-dithiodipropionic acid N-hydroxysuccinimide ester

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About This Item

Empirical Formula (Hill Notation):
C22H33N5O7S3
CAS Number:
142439-92-7
Molecular Weight:
575.72
MDL number:
MFCD00466919
UNSPSC Code:
12352203
PubChem Substance ID:
24891785
NACRES:
NA.46

Assay

>98%

form

powder

solubility

DMF: 50 mg/mL

storage temp.

−20°C

SMILES string

[H][C@]12CS[C@@H](CCCCC(=O)NCCNC(=O)CCSSCCC(=O)ON3C(=O)CCC3=O)[C@@]1([H])NC(=O)N2

InChI

1S/C22H33N5O7S3/c28-16(4-2-1-3-15-21-14(13-35-15)25-22(33)26-21)23-9-10-24-17(29)7-11-36-37-12-8-20(32)34-27-18(30)5-6-19(27)31/h14-15,21H,1-13H2,(H,23,28)(H,24,29)(H2,25,26,33)/t14-,15-,21-/m0/s1

InChI key

LWPHUVGDBNUVHA-GXZWQRSESA-N

Application

Biotinylation reagent incorporating a spacer with a cleavable disulfide linkage. Typically coupled to primary amine in the pH range 6.5-8.5. Cleavage of disulfide requires reducing agent allowing mild recovery of biotinylated compound.

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.

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Description
Pricing

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360D

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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M Ichikawa et al.
Bioorganic & medicinal chemistry letters, 11(13), 1769-1773 (2001-06-27)
We have prepared several mechanism-based affinity-labeling agents for possible use in isolating N-acetylglucosaminidase, in which an N-acetylglucosamine is linked to an o-monofluoro- or difluoro-methyl phenoxy glycoside with or without a cleavable disulfide group in the tether to biotin.
A reagent for covalently attaching biotin to proteins via a cleavable connector arm.
C A Mouton et al.
Archives of biochemistry and biophysics, 218(1), 101-108 (1982-10-01)
D Castelletti et al.
Clinical and experimental immunology, 136(2), 365-372 (2004-04-17)
Hodgkin's lymphoma patients treated with an anti-CD25 Ricin toxin A-chain (RTA)-based Immunotoxin (RFT5.dgA) develop an immune response against the toxic moiety of the immunoconjugate. The anti-RTA antibody response of 15 patients showing different clinical features and receiving different total amounts
Chemical probes of extended biological structures: synthesis and properties of the cleavable protein cross-linking reagent [35S]dithiobis(succinimidyl propionate).
A J Lomant et al.
Journal of molecular biology, 104(1), 243-261 (1976-06-14)

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