764493
5-[4-(1,2,4,5-Tetrazin-3-yl)benzylamino]-5-oxopentanoic acid
97%
Synonym(s):
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
Empirical Formula (Hill Notation):
C14H15N5O3
CAS Number:
Molecular Weight:
301.30
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Assay:
97%
Form:
solid
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.
signalword
Warning
hcodes
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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