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790443 Sigma-Aldrich

TCO-PEG3-maleimide

Synonym: trans-Cyclooctene-maleimide

  • Empirical Formula (Hill Notation) C26H41N3O8

  • Molecular Weight 523.62

  •  PubChem Substance ID 329768215

  •  NACRES NA.22

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper-Free Click Chemistry, Tetrazine/Strained-alkene Click Chemistry Reagents More...
Quality Level   100
storage temp.   −20°C
SMILES string   O=C(NCCCOCCOCCOCCCNC(CCN1C(C=CC1=O)=O)=O)OC2CCC/C=C/CC2
InChI   1S/C26H41N3O8/c30-23(12-15-29-24(31)10-11-25(29)32)27-13-6-16-34-18-20-36-21-19-35-17-7-14-28-26(33)37-22-8-4-2-1-3-5-9-22/h1-2,10-11,22H,3-9,12-21H2,(H,27,30)(H,28,33)/b2-1+
InChI key   BJZRPWAVCDJCTC-OWOJBTEDSA-N

Description

Packaging

5, 25 mg in clear glass bottle

Biochem/physiol Actions

Maleimide (thiol reactive) functionalized trans-cyclooctene derivative for incorporation of the cyclooctene moiety into thiol containing compounds or biomolecules. Trans-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. The PEG spacer allows for increased water solubility; less aggregation and an increased distance between the thiol to be modified and the reactive alkene.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Polyethylene Glycol (PEG) Selection Guide

Poly(ethylene glycol) (PEG) is a synthetic, hydrophilic, biocompatible polymer with widespread use in biomedical and other applications. PEGs are synthesized using a ring-opening polymerization of et...
Keywords: Adhesion, Bacterial conjugations, Click chemistry, Molecular biology, PEGylations, Polymerization reactions, Ring-opening polymerization

Peer-Reviewed Papers
15

References

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