924075
NHS ester-a-TCO
别名:
(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
InChI key
HKYXURAVXKJCHH-AWEZNQCLSA-N
SMILES string
O[C@@]1(CC(ON2C(CCC2=O)=O)=O)CC/C=C/CCC1
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
Quality Level
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)
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Jessica E Pigga et al.
Angewandte Chemie (International ed. in English), 60(27), 14975-14980 (2021-03-21)
trans-Cyclooctenes (TCOs) are essential partners in the fastest known bioorthogonal reactions, but current synthetic methods are limited by poor diastereoselectivity. Especially hard to access are hydrophilic TCOs with favorable physicochemical properties for live cell or in vivo experiments. Described is a
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