endo-BCN-PEG8-NHS ester Property

Density 

1.24±0.1 g/cm3(Predicted)

solubility 

Soluble in DMSO, DCM, DMF

form 

Liquid

pka

12.05±0.46(Predicted)

color 

Colorless to light yellow

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

endo-BCN-PEG8-NHS ester Chemical Properties,Usage,Production

Description

endo-BCN-PEG8-NHS ester is a monodisperse PEG linker containing an NHS ester group and a BCN group. It can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. The BCN group can react with azide-tagged biomolecules under copper free condition. The hydrophilic PEG spacer increases solubility in aqueous media.

Synthesis

To a solution of H2N-PEG8-COOH (822 mg, 1.86 mmol) in THF:H20 1 : 1 (20 mL) were added BCN-OSu (23) (651 mg, 2.23 mmol) and Et3N (774 μ, 5.59 mmol). The reaction was stirred at r.t. for 1.5 h andd acidified to pH 1 followed by extraction with EtOAc (3 x 35 mL). The combined organic layers were dried over Na2S04, filtered and the solvent removed under reduced pressure. The crude product was then dissolved in dry DCM (20 mL) and subsequently DCC (461 mg, 2.23 mmol) and NHS (257 mg, 2.23 mmol) were added. After stirring at r.t. for 1 h, the reaction was filtered and the filtrate concentrated in vacuo. Flash chromatography (MeCN, MeCN:H20 30: 1) afforded BCN-PEG8-COOSu.

in vitro

PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins.

structure and hydrogen bonding

endo-BCN-PEG8-NHS ester contains an NHS ester group and a BCN group on its ends. While the BCN group readily react with azide-tagged biomolecules, the NHS ester can be utilized for conjugation with amines bearing proteins, oligonucleotides, and other molecules. The hydrophilic PEG spacer increases the aqueous solubility of the resulting biomolecules.