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792594

Sigma-Aldrich

3,6-Dichloro-1,2,4,5-tetrazine

96%

Synonym(s):

Dichloro-s-tetrazine

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About This Item

Empirical Formula (Hill Notation):
C2Cl2N4
Molecular Weight:
150.95
MDL number:
MFCD22042702
UNSPSC Code:
12352200
PubChem Substance ID:
329768348
NACRES:
NA.22

Quality Level

100

Assay

96%

form

solid

availability

available only in USA

mp

146-151 °C

storage temp.

2-8°C

SMILES string

ClC1=NN=C(Cl)N=N1

InChI

1S/C2Cl2N4/c3-1-5-7-2(4)8-6-1

InChI key

HXXFMIAFWKZHDY-UHFFFAOYSA-N

Application

Reagent has been reported in stapling of complex peptides as a photochemical trigger. Professor Amos Smith and coworkers have displayed this application in several recent reports.

Other Notes

Peptide Stapling Reagents

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H242,H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP2088
MKCK7054
MKCC8964
MKBZ9274V
MKBW0350V

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Mohannad Abdo et al.
Organic letters, 14(13), 3518-3521 (2012-06-27)
The design, solid-phase synthesis, and photochemical validation of diverse peptide linchpins, containing the S,S-tetrazine phototrigger, have been achieved. Steady state irradiation or femtosecond laser pulses confirm their rapid photofragmentation. Attachment of peptides to the C- and N-termini will provide access
Joel R Courter et al.
The Journal of organic chemistry, 79(2), 759-768 (2013-12-24)
The design and synthesis of alanine-rich α-helical peptides constrained in a partially unfolded state by incorporation of the S,S-tetrazine phototrigger has been achieved, permitting, upon photochemical release, observation by 2D-IR spectroscopy of the subnanosecond conformational dynamics that govern the early
Stephen P Brown et al.
Journal of the American Chemical Society, 137(12), 4034-4037 (2015-03-21)
Protocols have been achieved that permit facile introduction of s-tetrazine into unprotected peptides and the protein, thioredoxin, between two cysteine sulfhydryl groups (i.e., staple), followed by photochemical release (i.e., unstaple) and regeneration of the peptide/protein upon removal of the cyano
Tetrazine phototriggers: probes for peptide dynamics.
Matthew J Tucker et al.
Angewandte Chemie (International ed. in English), 49(21), 3612-3616 (2010-04-15)
Matthew J Tucker et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(43), 17314-17319 (2013-10-10)
The relaxation of helical structures very close to equilibrium is observed via transient 2D IR spectroscopy. An initial distribution of synthetically distorted helices having an unnatural bridge linking the 10th and 12th residues of an alanine-rich α-helix is released to

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