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911887

Sigma-Aldrich

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl (bromoethyl)carbamate

Synonym(s):

Benzyl boronate tag, Bromoethyl boronic acid pinacol ester nuclear tag, Nucleus-targeting probe building block

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About This Item

Empirical Formula (Hill Notation):
C16H23BBrNO4
Molecular Weight:
384.07
UNSPSC Code:
12352101
NACRES:
NA.22

form

liquid

storage temp.

2-8°C

Application

This benzyl boronate tag is a synthetic means for the subcellular targeting of cargo to the nucleus. Intracellular targeting can be important for understanding the localization of metabolites, proteins, or chemical probes or to increase therapeutic efficacy by concentrating a drug at its site of action and reducing off-target effects. Localization specifically to the nucleus is typically achieved using peptide localization signals and/or relies on passive diffusion. It was recently demonstrated, however, that nuclear targeting could be accomplished instead with a small-molecule motif benzyl boronic acid via synergistic active and passive transport processes. Tang, et al, presented examples using this tag to deliver proteins to the nucleus by the importin α/β pathway, including fluorescent proteins, ribonuclease A (RNase A), and chymotrypsin. The conjugation of this nucleus-targeting building block to other proteins or small molecules will facilitate nuclear localization in varied chemical biology experiments.

Other Notes

Active Targeting of the Nucleus Using Nonpeptidic Boronate Tags

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Rui Tang et al.
Journal of the American Chemical Society, 139(25), 8547-8551 (2017-06-10)
Active intracellular transport is a central mechanism in cell biology, directed by a limited set of naturally occurring signaling peptides. Here, we report the first nonpeptide moiety that recruits intracellular transport machinery for nuclear targeting. Proteins synthetically modified with a

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