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764701

Sigma-Aldrich

2,5-Dioxo-1-pyrrolidinyl 5-[4-(1,2,4,5-tetrazin-3-yl)benzylamino]-5-oxopentanoate

≥90%

Sinónimos:

5-Oxo-5-[[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methyl]amino]pentanoic acid 2,5-dioxo-1-pyrrolidinyl ester, Benzylamino tetrazine N-hydroxysuccinimidyl ester, Benzylaminotetrazine-NHS, Bz-Tz-NHS

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About This Item

Fórmula empírica (notación de Hill):
C18H18N6O5
Número de CAS:
1244040-64-9
Peso molecular:
398.37
UNSPSC Code:
12352200
PubChem Substance ID:
329767137
NACRES:
NA.22

assay

≥90%

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

NHS ester

storage temp.

−20°C

SMILES string

O=C(CCCC(ON1C(CCC1=O)=O)=O)NCC(C=C2)=CC=C2C3=NN=CN=N3

InChI

1S/C18H18N6O5/c25-14(2-1-3-17(28)29-24-15(26)8-9-16(24)27)19-10-12-4-6-13(7-5-12)18-22-20-11-21-23-18/h4-7,11H,1-3,8-10H2,(H,19,25)

InChI key

QDUUJWMNSUXICN-UHFFFAOYSA-N

Application

2,5-Dioxo-1-pyrrolidinyl 5-[4-(1,2,4,5-tetrazin-3-yl)benzylamino]-5-oxopentanoate may be used in the synthesis of Tz-PEG11-1,4,7-triazacyclononane-N,N,N-triacetate, a precursor for Al[18F]-NOTA-labeled tetrazine radio ligand useful in 18F-based pretargeted PET imaging system.
Succinimidyl ester functionalized tetrazine for inverse electron demand Diels-Alder cycloaddition reactions. Succinimidyl ester will react with amines for small molecule, biomolecule or surface modification. Tetrazine will react with strained alkenes such as transcyclooctene, norbornene and cyclopropene to yield a stable covalent linkage. Tetrazines have proven useful in bioorthogonal reactions for many biological imaging and bioconjugation applications.

Related product

Referencia del producto
Descripción
Precios

919950

3-(([1,1′-Biphenyl]-4-ylmethyl)thio)-6-methyl-1,2,4,5-tetrazine, >98%

924083

TAMRA-a-TCO

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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18F-Based Pretargeted PET Imaging Based on Bioorthogonal Diels?Alder Click Chemistry
Meyer JP, et al.
Bioconjugate Chemistry, 27(2), 298-301 (2015)
Specific Binding of Liposomal Nanoparticles through Inverse Electron?Demand Diels?Alder Click Chemistry.
Brand C, et al.
ChemistryOpen null
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Journal of visualized experiments : JoVE, (143) (2019-02-19)
While radioimmunotherapy (RIT) is a promising approach for the treatment of cancer, the long pharmacokinetic half-life of radiolabeled antibodies can result in high radiation doses to healthy tissues. Perhaps not surprisingly, several different strategies have been developed to circumvent this
18F-Labeling of Mannan for Inflammation Research with Positron Emission Tomography.
Li XG, et al.
ACS Medicinal Chemistry Letters, 7(9), 826-830 (2016)
Mark R Karver et al.
Bioconjugate chemistry, 22(11), 2263-2270 (2011-09-29)
1,2,4,5-Tetrazines have been established as effective dienes for inverse electron demand [4 + 2] Diels-Alder cycloaddition reactions with strained alkenes for over 50 years. Recently, this reaction pair combination has been applied to bioorthogonal labeling and cell detection applications; however
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