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764523

Sigma-Aldrich

(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate

Synonym(s):

(E)-4-Cycloocten-1-yl 2,5-dioxo-1-pyrrolidinyl ester carbonic acid, trans-4-Cycloocten-1-yl 2,5-dioxo-1-pyrrolidinyl carbonate, TCO-N-hydroxysuccinimidyl carbonate, TCO-NHS, TCO-carbonate

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About This Item

Empirical Formula (Hill Notation):
C13H17NO5
CAS Number:
Molecular Weight:
267.28
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

90-105 °C

functional group

NHS ester

storage temp.

−20°C

SMILES string

O=C(ON1C(CCC1=O)=O)O[C@@H]2CC/C=C/CCC2

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+/t10-/m1/s1

InChI key

OUGQJOKGFAIFAQ-TXXBHVLJSA-N

Application

(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.
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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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A pretargeted PET imaging strategy based on bioorthogonal Diels?Alder click chemistry.
Zeglis BM, et al.
Journal of Nuclear Medicine, 54(8), 1389-1396 (2013)
Bioorthogonal Probes for Polo?like Kinase 1 Imaging and Quantification.
Budin G, et al.
Angewandte Chemie (International Edition in English), 50(40), 9378-9381 (2011)
Ubiquitous detection of gram-positive bacteria with bioorthogonal magnetofluorescent nanoparticles
Chung HJ, et al.
ACS Nano, 5(11), 8834-8841 (2011)
On-chip bioorthogonal chemistry enables immobilization of in situ modified nanoparticles and small molecules for label-free monitoring of protein binding and reaction kinetics.
Tassa C, et al.
Lab on a chip, 12(17), 3103-3110 (2012)
Bioorthogonal chemistry amplifies nanoparticle binding and enhances the sensitivity of cell detection
Haun JB, et al.
Nature Biotechnology, 5(9), 660-665 (2010)

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