Bromoacetamido-PEG9-ethylcarbamoyl-C4-Boc

 Cat No.: BP-501864 4.5  

Bromoacetamido-PEG9-ethylcarbamoyl-C4-Boc is a heterobifunctional, PEG-based PROTAC linker featuring a bromoacetamide electrophile at one terminus and a tert-butyl ester-protected carboxyl functionality at the other, separated by a long, flexible PEG9 segment. The bromoacetamide group is designed to form a stable covalent bond with nucleophilic residues (commonly cysteine thiols) on a ligand-bearing warhead, enabling site-specific attachment of the linker to targeted protein-binding modules. The extended PEG chain provides conformational flexibility and improved solubility, helping maintain productive geometry between the recruited ligand and the E3 ligase-binding partner. In PROTAC construction, this linker supports controlled conjugation chemistry and can be used to tune linker length and polarity to optimize ternary complex formation and degradation potency. It is therefore valuable for systematic linker optimization and for experiments requiring robust, covalent tethering strategies in targeted protein degradation workflows.

Bromoacetamido-PEG9-ethylcarbamoyl-C4-Boc

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PROTAC Linker
Molecular Formula
C₃₂H₆₁BrN₂O₁₃
Molecular Weight
761.74

* For research and manufacturing use only. Not for human or clinical use.

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Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 6-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[(2-bromoacetyl)amino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethylamino]-6-oxohexanoate
InChI Key
NJDWEAZOLRKHDT-UHFFFAOYSA-N
InChI
InChI=1S/C32H61BrN2O13/c1-32(2,3)48-31(38)7-5-4-6-29(36)34-8-10-39-12-14-41-16-18-43-20-22-45-24-26-47-27-25-46-23-21-44-19-17-42-15-13-40-11-9-35-30(37)28-33/h4-28H2,1-3H3,(H,34,36)(H,35,37)
SMILES
CC(C)(C)OC(=O)CCCCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CBr

This Bromoacetamido-PEG9-ethylcarbamoyl-C4-Boc linker is engineered for efficient conjugation in PROTAC architectures, providing a PEG-based spacer that can tune linker length, polarity, and conformational flexibility while preserving bioorthogonal reactivity. Its bromoacetamide functionality enables targeted nucleophilic substitution to install protein-binding warheads or handle subsequent assembly steps. The Boc-protected group supports controlled functional group transformations during synthesis. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains an ether-rich PEG segment that confers hydrophilicity and conformational flexibility, connected to a bromoacetamide electrophile and an ethylcarbamoyl motif. A Boc-protected functionality provides acid-labile protection, while the bromoacetamide features a polarized carbon–bromine bond suitable for substitution.

Reactivity: The bromoacetamide group reacts with nucleophiles such as primary amines and thiols via an SN2-type substitution, forming stable C–N or C–S linkages. PROTAC assembly is typically performed under anhydrous or low-water conditions using polar aprotic solvents, with base selection tailored to maintain nucleophile reactivity while minimizing side reactions. Boc deprotection is commonly achieved under mild acid conditions when required for subsequent coupling steps.

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L

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
g/mol
g

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