924075

NHS ester-a-TCO

• Synonym(s): (E)-N-Hydroxysuccinyl 2-(1-ax-hydroxycyclooct-4-en-1-yl)acetate, 2,5-Dioxopyrrolidin-1-yl (R,E)-2-(1-hydroxycyclooct-4-en-1-yl)acetate, Amine-reactive axial 5-hydroxy-trans-cyclooctene
• Empirical Formula (Hill Notation): C₁₄H₁₉NO₅
• Molecular Weight: 281.30
• UNSPSC Code: 12352108
• NACRES: NA.22

Properties

• reaction suitability: reaction type: click chemistry; reactivity: amine reactive; reagent type: chemical modification reagent; reagent type: cross-linking reagent
• Quality Level: 100
• functional group: NHS ester
• storage temp.: −20°C
• SMILES string: O[C@@]1(CC(ON2C(CCC2=O)=O)=O)CC/C=C/CCC1

Description

Application

NHS ester-a-TCO is an axial trans-cyclooctene (a-TCO) for bioconjugation and protein labeling. NHS ester-a-TCO has an amine-reactive NHS ester, and the a-TCO reacts rapidly with tetrazines through Diels–Alder reactions, a type of bioorthogonal, copper-free click chemistry. As demonstrated by the Joe Fox lab in Pigga, et al, a-TCOs are more reactive and hydrophilic than standard TCOs, providing favorable physiochemical properties for live-cell and in vivo labeling.

Other new a-TCOs:

• TAMRA-a-TCO (924083)
• Alkyne-a-TCO (924091)
• Amine-a-TCO (924113)

Other Notes

General, Divergent Platform for Diastereoselective Synthesis of trans-Cyclooctenes with High Reactivity and Favorable Physiochemical Properties

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable