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(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate - ≥83.0%, high purity , CAS No.1191901-33-3

Item Number
E486554
Grouped product items
SKUSizeAvailabilityPrice Qty
E486554-1mg
1mg
In stock
$22.90
E486554-5mg
5mg
In stock
$91.90
E486554-25mg
25mg
In stock
$382.90
E486554-100mg
100mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$1,375.90

Basic Description

SynonymsTCO-NHS ester|1191901-33-3|TCO-NHS|(E)-Cyclooct-4-en-1-yl (2,5-dioxopyrrolidin-1-yl) carbonate|MFCD24386372|(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate|(E)-cyclooct-4-enyl 2,5-dioxopyrrolidin-1-yl carbonate|TCO-NHS Ester (equatorial)|2BX65M7XV6
Specifications & Purity≥83.0%
Storage TempStore at -20°C,Argon charged
Shipped InIce chest + Ice pads
Product Description

Description

Succinimidyl carbonate/NHS functionalized cyclooctene derivative for incorporation of the cyclooctene moiety into amine containing compounds or biomolecules. Cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1,2,4,5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging.(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate may be used in the synthesis of vancomycin-TCO that can bind to the cell wall of gram-positive bacteria, which can subsequently react with tetrazine (Tz) decorated magneto-fluorescent nanoparticles orthogonally. This bioorthogonal labeling method is useful for the detection of gram-positive bacteria.

Names and Identifiers

Pubchem Sid488201927
IUPAC Name [(4E)-cyclooct-4-en-1-yl] (2,5-dioxopyrrolidin-1-yl) carbonate
INCHI InChI=1S/C13H17NO5/c15-11-8-9-12(16)14(11)19-13(17)18-10-6-4-2-1-3-5-7-10/h1-2,10H,3-9H2/b2-1+
InChi Key OUGQJOKGFAIFAQ-OWOJBTEDSA-N
Canonical SMILES C1CC=CCCC(C1)OC(=O)ON2C(=O)CCC2=O
Isomeric SMILES C1C/C=C/CCC(C1)OC(=O)ON2C(=O)CCC2=O
PubChem CID 58490201
Molecular Weight 267.28

Certificates

Certificate of Analysis(COA)

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6 results found

Lot NumberCertificate TypeDateItem
F2302212Certificate of AnalysisMay 08, 2023 E486554
F2302213Certificate of AnalysisMay 08, 2023 E486554
F2302214Certificate of AnalysisMay 08, 2023 E486554
F2302215Certificate of AnalysisMay 08, 2023 E486554
F2302216Certificate of AnalysisMay 08, 2023 E486554
F2302217Certificate of AnalysisMay 08, 2023 E486554

Chemical and Physical Properties

SensitivityMoisture sensitive;Light sensitive;Heat sensitive

Safety and Hazards(GHS)

Signal Warning
Hazard Statements

H315:Causes skin irritation

H319:Causes serious eye irritation

H335:May cause respiratory irritation

H302:Harmful if swallowed

Precautionary Statements

P261:Avoid breathing dust/fume/gas/mist/vapors/spray.

P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing.

Related Documents

References

1. Melissa L Blackman,Maksim Royzen,Joseph M Fox.  (2008-09-19)  Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity..  Journal of the American Chemical Society,  130  ((41)): (13518-13519).  [PMID:18798613]
2. Neal K Devaraj,Ralph Weissleder,Scott A Hilderbrand.  (2008-12-05)  Tetrazine-based cycloadditions: application to pretargeted live cell imaging..  Bioconjugate chemistry,  19  ((12)): (2297-2299).  [PMID:19053305]
3. Mark R Karver, Ralph Weissleder, Scott A Hilderbrand,.  (2011-09-29)  Synthesis and evaluation of a series of 1,2,4,5-tetrazines for bioorthogonal conjugation..  Bioconjugate chemistry,  22  ((11)): ( 2263-2270 ).  [PMID:21950520]
4. Katherine S Yang,Ghyslain Budin,Thomas Reiner,Claudio Vinegoni,Ralph Weissleder.  (2012-05-31)  Bioorthogonal imaging of aurora kinase A in live cells..  Angewandte Chemie (International ed. in English),  51  ((27)): (6598-6603).  [PMID:22644700]

Solution Calculators