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924075

NHS ester-a-TCO

Name: NHS ester-a-TCO
Brand: ALDRICH

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

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Properties

Quality Level

100

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

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

MKCT8249

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

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

Global Trade Item Number

SKU	GTIN
924075-50MG	04065267182025
924075-5MG	04065267182032