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Merck
CN

764523

(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
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form

solid

Quality Segment

reaction suitability

reaction type: click chemistry, reagent type: linker

technique(s)

targeted protein degradation: suitable

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

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable



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