764493
5-[4-(1,2,4,5-Tetrazin-3-yl)benzylamino]-5-oxopentanoic acid
97%
别名:
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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关于此项目
经验公式（希尔记法）:
C14H15N5O3
化学文摘社编号:
分子量:
301.30
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Assay:
97%
Form:
solid
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)
SMILES string
OC(CCCC(NCC(C=C1)=CC=C1C2=NN=CN=N2)=O)=O
InChI key
KWNYIZNORNUUJQ-UHFFFAOYSA-N
assay
97%
form
solid
reaction suitability
reagent type: linker
mp
163-170 °C (decomposition)
functional group
carboxylic acid
storage temp.
−20°C
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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
Melissa L Blackman et al.
Journal of the American Chemical Society, 130(41), 13518-13519 (2008-09-19)
Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water
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