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924075

Sigma-Aldrich

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

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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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