Fmoc-PEG8-NHS ester

 CAS No.: 1334170-03-4  Cat No.: BP-500488  Purity: >95% 4.5  

Fmoc-PEG8-NHS ester is a heterobifunctional PEG-based linker designed for efficient coupling in PROTAC and targeted protein degradation workflows. Structurally, it combines an Fmoc-protected terminus with a terminal N-hydroxysuccinimide (NHS) ester, providing a flexible hydrophilic chain of approximately eight ethylene glycol units and a reactive amine-targeting handle. In PROTAC construction, the NHS ester forms stable amide bonds with primary amines on ligands (e.g., lysine-containing residues or aminated targeting moieties), while the Fmoc group enables controlled functionalization and compatibility with solid-phase or orthogonal synthetic strategies. This linker’s extended PEG spacer can improve solubility, reduce steric clashes between the recruitment and warhead components, and help maintain productive geometry for ternary complex formation. As a result, it is valuable for preparing conjugates and optimizing linker length and flexibility in experimental targeted degradation studies.

Fmoc-PEG8-NHS ester

Structure of 1334170-03-4

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Category
PROTAC Linker
Molecular Formula
C38H52N2O14
Molecular Weight
760.82
Appearance
Pale Yellow or Colorless Oily Liquid

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

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Purity
>95%
Solubility
Soluble in DCM, DMF, DMSO
Appearance
Pale Yellow or Colorless Oily Liquid
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Fmoc-NH-PEG8-NHS ester; Fmoc-PEG8-C2-NHS ester; Fmoc-NH-PEG8-NHS; FmocNH-PEG8-CH2CH2COONHS; Fmoc-PEG8-CH2CH2-NHS ester; Fmoc-N-amido-PEG8-NHS ester; 9H-Fluoren-9-ylmethyl {27-[(2,5-dioxo-1-pyrrolidinyl)oxy]-27-oxo-3,6,9,12,15,18,21,24-octaoxaheptacos-1-yl}carbamate; Carbamic acid, N-[27-[(2,5-dioxo-1-pyrrolidinyl)oxy]-27-oxo-3,6,9,12,15,18,21,24-octaoxaheptacos-1-yl]-, 9H-fluoren-9-ylmethyl ester; 2,5-Dioxopyrrolidin-1-yl 1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16,19,22,25,28-nonaoxa-4-azahentriacontan-31-oate
Density
1.28±0.1 g/cm3 (Predicted)
InChI Key
AMSAHSNOOQLQOU-UHFFFAOYSA-N
InChI
InChI=1S/C38H52N2O14/c41-35-9-10-36(42)40(35)54-37(43)11-13-45-15-17-47-19-21-49-23-25-51-27-28-52-26-24-50-22-20-48-18-16-46-14-12-39-38(44)53-29-34-32-7-3-1-5-30(32)31-6-2-4-8-33(31)34/h1-8,34H,9-29H2,(H,39,44)
SMILES
C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCNC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-PEG8-NHS ester is an activated polyethylene glycol linker designed for efficient conjugation in PROTAC workflows, enabling stable attachment of targeting ligands to protein-binding modules. Its PEG spacer improves solubility and can help mitigate steric constraints, while the Fmoc group supports compatibility with orthogonal protection strategies. The NHS ester facilitates rapid amide-bond formation under mild conditions, making it well suited for constructing PROTACs and related targeted conjugates; detailed structural and reactivity considerations are provided below.

Structure: The linker combines an Fmoc-protected aromatic carbamate moiety with a PEG chain and a terminal N-hydroxysuccinimide ester. It contains an NHS-activated carboxylate, ether linkages within the PEG backbone, and aromatic and carbamate functional groups, yielding a flexible, hydrophilic spacer with enhanced aqueous compatibility.

Reactivity: The NHS ester reacts with primary amines to form stable amide bonds, typically using buffered aqueous or mixed solvent systems at near-neutral pH to preserve NHS reactivity. The mechanism proceeds via nucleophilic acyl substitution, generating an amide and releasing NHS. Commonly used solvents include water or polar organic co-solvents, and no special catalysts are generally required; careful control of pH and amine equivalents helps drive efficient coupling.

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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

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
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