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764493

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

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

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:

1225146-53-1

Molecular Weight:

301.30

NACRES:

NA.22

PubChem Substance ID:

329767124

UNSPSC Code:

12352200

MDL number:

MFCD23098727

Assay:

97%

Form:

solid

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Properties

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

Description

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.

pictograms

GHS07

signalword

Warning

hcodes

H302,H315,H319,H335

pcodes

P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338

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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Certificates of Analysis (COA)

Lot/Batch Number

MKCK9998

MKBL7578V

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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