Cbz-N-amido-PEG5-acetic acid

 CAS No.: 1449390-66-2  Cat No.: BP-501717  Purity: >98% 4.5  

Cbz-N-amido-PEG5-acetic acid is a polyethylene glycol–based linker building block featuring a Cbz-protected amide terminus and a terminal acetic acid functionality, providing a defined PEG chain length and a stable amide linkage for conjugation. The PEG segment imparts conformational flexibility and aqueous solubility, which are important for minimizing steric interference between the warhead and the E3 ligase-binding ligand in PROTAC constructs. In targeted protein degradation workflows, this linker can be used to connect a carboxyl-reactive or amide-forming handle on one PROTAC module to an amine-containing partner, enabling controlled spatial separation and improved effective concentration at the ternary complex interface. Its bifunctional design supports modular synthesis of PROTACs and related bifunctional degraders, facilitating systematic optimization of linker length and attachment chemistry to enhance degradation potency and selectivity while maintaining synthetic tractability for experimental studies.

Cbz-N-amido-PEG5-acetic acid

Structure of 1449390-66-2

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Category
PROTAC Linker
Molecular Formula
C₂₀H₃₁NO₉
Molecular Weight
429.46
Appearance
Viscous Liquid

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

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Purity
>98%
Appearance
Viscous Liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-[2-[2-[2-(phenylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic acid
Synonyms
Cbz-NH-PEG5-CH2COOH; Cbz-NH-PEG5-acetic acid
Boiling Point
590.4±50.0 °C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
JEVLWNSJFGPKCP-UHFFFAOYSA-N
InChI
InChI=1S/C20H31NO9/c22-19(23)17-29-15-14-28-13-12-27-11-10-26-9-8-25-7-6-21-20(24)30-16-18-4-2-1-3-5-18/h1-5H,6-17H2,(H,21,24)(H,22,23)
SMILES
C1=CC=C(C=C1)COC(=O)NCCOCCOCCOCCOCCOCC(=O)O

Cbz-N-amido-PEG5-acetic acid is a PEG-based linker building block designed for constructing PROTACs and related targeted protein degradation conjugates. Its ether-rich, flexible poly(ethylene glycol) segment can improve solubility and provide spatial separation between binding elements, while the Cbz-protected amino functionality supports controlled coupling strategies. The Cbz group enables orthogonal deprotection when assembling multi-component degraders. Detailed structural and reactivity considerations are provided below.

Structure: The molecule contains a Cbz-protected amino group linked to a PEG chain terminating in an acetic acid group. It features ether linkages within the PEG segment, an aromatic carbamate (Cbz), and carboxylic acid functionality suitable for amide formation. Overall, it is flexible and polar.

Reactivity: The acetic acid end can be activated for amide bond formation using standard coupling approaches such as carbodiimide-based reagents with additive bases, typically in polar aprotic solvents. The Cbz group supports selective deprotection under hydrogenation conditions to reveal an amine for subsequent conjugation. These steps align with common PROTAC linker assembly logic: controlled functional group interconversion, then final conjugation to ligands under mild conditions.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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