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Merck
CN

804665

Sigma-Aldrich

Azido-PEG4-phenyloxadiazole methylsulfone

≥95%

Synonym(s):

2-(4-(2-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)ethoxy)phenyl)-5-(methylsulfonyl)-1,3,4-oxadiazole

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About This Item

Empirical Formula (Hill Notation):
C17H23N5O7S
Molecular Weight:
441.46
MDL number:
MFCD26960813
UNSPSC Code:
12352200
PubChem Substance ID:
329768888
NACRES:
NA.22

Key Documents

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Assay

≥95%

form

powder

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

azide

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=S(C(O1)=NN=C1C2=CC=C(OCCOCCOCCOCCN=[N+]=[N-])C=C2)(C)=O

InChI

1S/C17H23N5O7S/c1-30(23,24)17-21-20-16(29-17)14-2-4-15(5-3-14)28-13-12-27-11-10-26-9-8-25-7-6-19-22-18/h2-5H,6-13H2,1H3

InChI key

UPMDUJBOYVOHRH-UHFFFAOYSA-N

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Application

This is a heterobifunctional crosslinker that has a methylsulfonyl group to react with thiols on one end. The methylsulfonyl group is very specific for reacting with thiols in proteins at pH 5.8 to 8.0 and forms a bond that is more stable than that when using maleimide chemistry. The other end of the crosslinker contains an azide group that can react with an alkyne through Cu-mediated click chemistry or with strained alkynes in a Cu-free reaction.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN5825
MKCF3689
MKBX9525V

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Rapid, stable, chemoselective labeling of thiols with Julia-Kocieński-like reagents: a serum-stable alternative to maleimide-based protein conjugation.
Narihiro Toda et al.
Angewandte Chemie (International ed. in English), 52(48), 12592-12596 (2013-10-15)

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