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
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About This Item
Empirical Formula (Hill Notation):
C14H19NO5
Molecular Weight:
281.30
UNSPSC Code:
12352108
NACRES:
NA.22
Quality Segment
reaction suitability
reaction type: click chemistry, reactivity: amine reactive, reagent type: chemical modification reagent, reagent type: cross-linking reagent
functional group
NHS ester
storage temp.
−20°C
SMILES string
O[C@@]1(CC(ON2C(CCC2=O)=O)=O)CC/C=C/CCC1
InChI key
HKYXURAVXKJCHH-AWEZNQCLSA-N
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:
Other new a-TCOs:
- TAMRA-a-TCO (924083)
- Alkyne-a-TCO (924091)
- Amine-a-TCO (924113)
Storage Class
11 - Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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