Fmoc-N-amido-PEG6-acetic acid

 CAS No.: 437655-96-4  Cat No.: BP-500518  Purity: ≥95% 4.5  

Fmoc-N-amido-PEG6-acetic acid is a polyethylene glycol–based linker building block featuring an N-amide functionality and a terminal acetic acid group, with an Fmoc (fluorenylmethoxycarbonyl) protecting group suitable for stepwise solid-phase or solution-phase synthesis. Structurally, it provides a flexible, hydrophilic PEG chain of moderate length that can reduce steric bias and improve solubility of conjugates, while the carboxylic acid enables reliable coupling to ubiquitin-ligase ligands, warheads, or other PROTAC components through standard amide-forming chemistries. In PROTAC design, such PEG linkers help position the two binding elements in a productive geometry for ternary complex formation and can mitigate unfavorable intramolecular interactions, thereby supporting efficient recruitment of the target protein to the E3 ligase. As a versatile, chemically robust intermediate, it is valuable for constructing degraders and related targeted protein conjugates where controlled linker length, aqueous compatibility, and modular functional group handling are critical for systematic structure–activity studies.

Fmoc-N-amido-PEG6-acetic acid

Structure of 437655-96-4

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Category
PROTAC Linker
Molecular Formula
C29H39NO10
Molecular Weight
561.62
Related CAS
675606-79-8 (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
≥95%
Solubility
Soluble in DMSO (10 mm)
Appearance
Pale Yellow or Colorless Oily Matter
ShelfLife
≥ 2 years
Storage
Store at 2-8°C
Shipping
Room temperature, or blue ice upon request.
IUPACName
2-[2-[2-[2-[2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic acid
Synonyms
Fmoc-NH-PEG6-CH2COOH; 20-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3,6,9,12,15,18-hexaoxaicosanoic acid; 1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13,16,19,22-heptaoxa-4-azatetracosan-24-oic acid; 2,7,10,13,16,19,22-Heptaoxa-4-azatetracosan-24-oic acid, 1-(9H-fluoren-9-yl)-3-oxo-; 20-(fluoren-9-ylmethyloxycarbonylamino)-3,6,9,12,15,18-hexaoxaeicosanoic acid; 5,8,11,14,17,20-Hexaoxa-2-azadocosanedioic acid, 1-(9H-fluoren-9-ylmethyl) ester; Fmoc-PEG6-acetic acid
Boiling Point
727.5±60.0°C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
HANLHKUCDRJGKX-UHFFFAOYSA-N
InChI
InChI=1S/C29H39NO10/c31-28(32)22-39-20-19-38-18-17-37-16-15-36-14-13-35-12-11-34-10-9-30-29(33)40-21-27-25-7-3-1-5-23(25)24-6-2-4-8-26(24)27/h1-8,27H,9-22H2,(H,30,33)(H,31,32)
SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCOCCOCCOCCOCCOCCOCC(=O)O

Fmoc-N-amido-PEG6-acetic acid is a polyethylene glycol (PEG)-based linker building block designed for constructing PROTACs and other bifunctional degraders. Its PEG spacer supports favorable solubility and conformational flexibility, while the Fmoc-protected amide functionality enables stepwise synthetic assembly under standard peptide/PROTAC linker workflows. The resulting conjugates can be tailored to connect ligands to an E3-recruiting or target-binding module with controlled spacing; detailed structural and reactivity considerations are provided below.

Structure: The linker contains an Fmoc-protected amide linked to a PEG chain and terminates in an acetic acid functionality. It features aromatic carbamate (Fmoc), amide and carboxylic acid groups, and multiple ether linkages within the PEG segment, providing flexible, hydrophilic character and improved handling in organic synthesis.

Reactivity: The carboxylic acid can be activated for amide-bond formation using common coupling strategies (e.g., carbodiimide-based systems with additives such as nucleophilic catalysts), typically in polar aprotic solvents. The Fmoc group is compatible with orthogonal protection/deprotection logic, allowing controlled coupling after deprotection. Mechanistically, PROTAC linker assembly proceeds via formation of activated carboxyl intermediates followed by nucleophilic attack by an amine-bearing ligand or spacer.

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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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