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Merck
CN
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文件

924075

Sigma-Aldrich

NHS ester-a-TCO

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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
经验公式（希尔记法）:
C14H19NO5
分子量:
281.30
UNSPSC代码:
12352108
NACRES:
NA.22

反应适用性

reaction type: click chemistry
reactivity: amine reactive
reagent type: chemical modification reagent
reagent type: cross-linking reagent

质量水平

100

官能团

NHS ester

储存温度

−20°C

SMILES字符串

O[C@@]1(CC(ON2C(CCC2=O)=O)=O)CC/C=C/CCC1

应用

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)

其他说明

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

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说明
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WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

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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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