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Merck
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764493

Sigma-Aldrich

5-[4-(1,2,4,5-Tetrazin-3-yl)benzylamino]-5-oxopentanoic acid

97%

Sinónimos:

5-Oxo-5-[[[4-(1,2,4,5-tetrazin-3-yl)phenyl]methyl]amino]pentanoic acid, Benzylamino tetrazine acid, Bz-Tz-acid

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About This Item

Fórmula empírica (notación de Hill):
C14H15N5O3
Número de CAS:
1225146-53-1
Peso molecular:
301.30
MDL number:
MFCD23098727
UNSPSC Code:
12352200
PubChem Substance ID:
329767124
NACRES:
NA.22

assay

97%

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

163-170 °C (decomposition)

functional group

carboxylic acid

storage temp.

−20°C

SMILES string

OC(CCCC(NCC(C=C1)=CC=C1C2=NN=CN=N2)=O)=O

InChI

1S/C14H15N5O3/c20-12(2-1-3-13(21)22)15-8-10-4-6-11(7-5-10)14-18-16-9-17-19-14/h4-7,9H,1-3,8H2,(H,15,20)(H,21,22)

InChI key

KWNYIZNORNUUJQ-UHFFFAOYSA-N

Application

5-[4-(1,2,4,5-Tetrazin-3-yl)benzylamino]-5-oxopentanoic acid may be used in the synthesis of a PEG-tetrazine (PEG-Tz) macromer via acid-amine conjugation. This macromer can undergo click reaction with norbornene-functionalized peptides to form hydrogels that is useful for 3D cell culture.
Acid functionalized tetrazine for inverse electron demand Diels-Alder cycloaddition reactions. The 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

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

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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Facile and efficient Lewis acid catalyzed synthesis of an asymmetric tetrazine useful for bio-orthogonal click chemistry applications
Alge DL, et al.
Tetrahedron Letters, 54(41), 5639-5641 (2013)
Synthetically tractable click hydrogels for three-dimensional cell culture formed using tetrazine?norbornene chemistry
Alge DL, et al.
Biomacromolecules, 14(4), 949-953 (2013)
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
Neal K Devaraj et al.
Bioconjugate chemistry, 19(12), 2297-2299 (2008-12-05)
Bioorthogonal tetrazine cycloadditions have been applied to live cell labeling. Tetrazines react irreversibly with the strained dienophile norbornene forming dihydropyrazine products and dinitrogen. The reaction is high yielding, selective, and fast in aqueous media. Her2/neu receptors on live human breast
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