Fmoc-N-amido-PEG1-acid

 CAS No.: 1654740-73-4  Cat No.: BP-501196  Purity: >98% 4.5  

Fmoc-N-amido-PEG1-acid is a polyethylene glycol–containing, Fmoc-protected amino acid derivative designed as a PROTAC linker building block for constructing conjugates with controlled hydrophilicity and spacing. Structurally, it combines an Fmoc (9-fluorenylmethoxycarbonyl) group for base-stable, solid-phase–compatible amine protection with a single ethylene glycol unit and a terminal carboxylic acid, enabling straightforward coupling to amine-bearing ligands or linker fragments via standard amide-forming chemistries. In PROTAC architectures, PEG segments are widely used to modulate solubility, reduce nonproductive hydrophobic contacts, and tune the effective distance and conformational freedom between the target-binding moiety and the E3-recruiting ligand. This compound therefore supports the rational optimization of linker length and polarity, facilitating systematic structure–activity relationship studies and improving the reliability of degradation assays by enhancing compound handling and minimizing aggregation.

Fmoc-N-amido-PEG1-acid

Structure of 1654740-73-4

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Category
PROTAC Linker
Molecular Formula
C20H21NO5
Molecular Weight
355.38
Related CAS
850312-72-0 (polymer)
Appearance
Pale Yellow or Colorless Oily Matter

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

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Purity
>98%
Solubility
Soluble in DMSO
Appearance
Pale Yellow or Colorless Oily Matter
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]propanoic acid
Synonyms
Fmoc-6-Amino-4-oxahexanoic acid; Fmoc-N-amido-PEG1-acid; Fmoc-NH-PEG1-C2-acid; Fmoc-NH-PEG1-CH2CH2COOH; 6-(Fmoc-amino)-4-oxahexanoic Acid; Fmoc-AEP; Fmoc-PEG1-propionic acid; Propanoic acid, 3-[2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]ethoxy]-; 3-[2-(Fmoc-amino)ethoxy]propanoic acid
Boiling Point
589.9±40.0 °C at 760 mmHg
Density
1.261±0.06 g/cm3 (Predicted)
InChI Key
LHBCOPWWQKLECJ-UHFFFAOYSA-N
InChI
InChI=1S/C20H21NO5/c22-19(23)9-11-25-12-10-21-20(24)26-13-18-16-7-3-1-5-14(16)15-6-2-4-8-17(15)18/h1-8,18H,9-13H2,(H,21,24)(H,22,23)
SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCOCCC(=O)O

This Fmoc-N-amido-PEG1-acid linker is designed for modular assembly of PROTAC constructs, providing a chemically addressable handle for conjugation while maintaining a flexible, hydrophilic segment that can support productive ternary-complex formation. Its Fmoc-protected amide functionality enables controlled stepwise synthesis, and the acid terminus offers a reliable site for coupling to targeting or E3-ligand fragments. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains an Fmoc-protected amide linked to a short polyethylene glycol unit terminating in a carboxylic acid. It features aromatic carbamate protection (Fmoc), amide and ester-like connectivity to the PEG segment, and a terminal carboxyl group suitable for activation. Overall, it is polar and conformationally flexible.

Reactivity: The carboxylic acid is typically converted to an activated ester or acylating intermediate using standard coupling chemistries, followed by nucleophilic amide formation with an appropriate amine-bearing PROTAC fragment. Fmoc can be removed under base-promoted conditions to expose the nucleophilic nitrogen for subsequent coupling. Commonly used solvents include polar aprotic media, and coupling catalysts/activators depend on the chosen activation mode.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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