Acid-PEG5-NHS ester

 CAS No.: 1343476-41-4  Cat No.: BP-501159  Purity: ≥95% 4.5  

Acid-PEG5-NHS ester is a heterobifunctional polyethylene glycol (PEG) linker featuring one free carboxylic acid terminus and one N-hydroxysuccinimide (NHS) ester terminus, enabling efficient amide-bond formation with primary amines on target-binding ligands (e.g., lysine-bearing peptides or amine-functionalized small molecules). Structurally, it provides a flexible PEG chain of moderate length that can improve aqueous solubility, reduce nonspecific hydrophobic interactions, and help spatially separate the conjugated warhead from the recruited-ligand moiety in PROTAC constructs. In targeted protein degradation design, the NHS ester reacts with an amine-containing component while the free acid remains available for separate activation and coupling, yielding stable amide linkages that preserve the geometry required for ternary complex formation. Its value lies in providing a robust, chemoselective conjugation handle that facilitates modular PROTAC synthesis and optimization of linker length and flexibility to tune degradation efficiency and selectivity.

Acid-PEG5-NHS ester

Structure of 1343476-41-4

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Category
PROTAC Linker
Molecular Formula
C18H29NO11
Molecular Weight
435.43
Related CAS
1643594-31-3 (polymer)
Appearance
Pale Yellow Oily Matter

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

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Purity
≥95%
Appearance
Pale Yellow Oily Matter
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-[2-[2-[3-(2,5-dioxopyrrolidin-1-yl)oxy-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Acid-C2-PEG5-NHS ester; COOH-PEG5-SPA; COOH-PEG5-NHS; 4,7,10,13,16-Pentaoxanonadecanedioic acid, 1-(2,5-dioxo-1-pyrrolidinyl) ester; 19-((2,5-dioxopyrrolidin-1-yl)oxy)-19-oxo-4,7,10,13,16-pentaoxanonadecanoic acid; 4,7,10,13,16-Pentaoxanonadecan-1-oic acid, 19-[(2,5-dioxo-1-pyrrolidinyl)oxy]-19-oxo-
Boiling Point
574.8±60.0°C (Predicted)
Density
1.30±0.1 g/cm3 (Predicted)
InChI Key
QMACGMMKGUAJOY-UHFFFAOYSA-N
InChI
InChI=1S/C18H29NO11/c20-15-1-2-16(21)19(15)30-18(24)4-6-26-8-10-28-12-14-29-13-11-27-9-7-25-5-3-17(22)23/h1-14H2,(H,22,23)
SMILES
C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCC(=O)O

Acid-PEG5-NHS ester is a polyethylene glycol (PEG)-based linker designed for efficient conjugation in targeted protein degradation workflows. Its activated N-hydroxysuccinimide (NHS) ester enables rapid formation of stable amide bonds with primary amine groups, supporting the modular assembly of PROTACs and related bifunctional degraders. The PEG spacer can improve solubility and provide conformational flexibility, which may help maintain productive geometry between ligand domains. Detailed structural and reactivity considerations are provided below.

Structure: Acid-PEG5-NHS ester contains a PEG chain terminated by a carboxylic acid and an NHS-activated ester. It features ester and amide-forming functional groups, with ether linkages along the PEG backbone. The molecule is typically water-compatible and shows enhanced hydrophilicity due to the PEG segment.

Reactivity: The NHS ester reacts with primary amines to form amide bonds under mildly basic aqueous or mixed solvent conditions, commonly using buffering systems that preserve NHS reactivity. The mechanism involves nucleophilic attack by the amine on the activated carbonyl, followed by NHS leaving-group departure. No special catalysts are generally required; careful control of pH and avoidance of competing nucleophiles are important.

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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

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
g/mol
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