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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%

Synonym(s):

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

Empirical Formula (Hill Notation):
C18H18N6O5
CAS Number:
1244040-64-9
Molecular Weight:
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.

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Description
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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCB3287V
MKBL7579V

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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
Rosemery Membreno et al.
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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