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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

Quality Level

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.

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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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)
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)
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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