Cbz-N-amido-PEG2-acetic acid

Name: Cbz-N-amido-PEG2-acetic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 165454-06-8

Cat No.: BP-501651 4.5

Cbz-N-amido-PEG2-acetic acid is a PEG-based linker building block featuring a terminal acetic acid for carboxylate coupling and an N-amido interface suitable for amide-bond formation, while the Cbz (benzyloxycarbonyl) group provides an orthogonal protecting handle during PROTAC linker synthesis. Structurally, it comprises a short two–ethylene glycol unit that imparts aqueous solubility and conformational flexibility, together with a defined linkage point that can connect to either a ligand-bearing amine or an activated carboxylate partner. In PROTAC design, such PEG spacers help tune the effective distance and relative orientation between the target-binding moiety and the E3 ligase ligand, thereby improving productive ternary complex formation and degradation efficiency. As a modular intermediate, it is valuable for preparing systematic linker libraries, enabling controlled variation of hydrophilicity and attachment geometry in targeted protein degradation experiments.

Structure of 165454-06-8

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Category

PROTAC Linker

Molecular Formula

C₁₄H₁₉NO₆

Molecular Weight

297.30

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

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Storage

Pure form, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

2-[2-[2-(phenylmethoxycarbonylamino)ethoxy]ethoxy]acetic acid

Synonyms

CBZ-NH-PEG2-CH2COOH; Cbz-8-amino-3,6-dioxaoctanoic acid DCHA; 3-Oxo-1-phenyl-2,7,10-trioxa-4-azadodecan-12-oic acid; 10-oxo-12-phenyl-3,6,11-Trioxa-9-azadodecanoic acid

Boiling Point

506.6±45.0 °C at 760 mmHg

Density

1.2±0.1 g/cm3

InChI Key

GWUWSVXMAZFFNT-UHFFFAOYSA-N

InChI

InChI=1S/C14H19NO6/c16-13(17)11-20-9-8-19-7-6-15-14(18)21-10-12-4-2-1-3-5-12/h1-5H,6-11H2,(H,15,18)(H,16,17)

SMILES

C1=CC=C(C=C1)COC(=O)NCCOCCOCC(=O)O

This linker, Cbz-N-amido-PEG2-acetic acid, is designed to serve as a versatile polyethylene glycol-based spacer in PROTAC assemblies, enabling controlled spatial separation between ligand modules. Its PEG character supports favorable solubility and conformational flexibility for modular conjugation workflows. The Cbz-protected amino functionality provides a practical handle for stepwise linker elaboration and coupling strategies. The detailed structural and reactivity considerations are provided below.

Structure: The molecule combines a Cbz-protected amino group with a short PEG segment and a terminal acetic acid functionality. It contains an aromatic carbamate (Cbz), a terminal carboxylic acid, and ether linkages within the PEG chain. These features impart hydrophilicity, hydrogen-bonding capacity, and conformational mobility.

Reactivity: PROTAC construction typically uses the terminal carboxylic acid for amide-bond formation with amine-bearing ligands or intermediate handles. Coupling can be performed under standard peptide-coupling conditions using activating agents and base in compatible polar aprotic solvents, followed by Cbz deprotection when needed to expose a free amine for subsequent conjugation. The PEG ether segment is generally stable under these mild conditions, supporting modular synthesis workflows.

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* 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