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Bis-(m-PEG8-amido)-hexanoic acid

Bis-(m-PEG8-amido)-hexanoic acid

Name: Bis-(m-PEG8-amido)-hexanoic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 2353409-77-3

Cat No.: BP-501621 4.5

Bis-(m-PEG8-amido)-hexanoic acid is a bifunctional PEG-based linker designed for constructing PROTACs and related targeted protein degradation conjugates. Structurally, it comprises a central hexanoic acid scaffold bearing two amide-linked m-PEG8 chains, providing a flexible, hydrophilic spacer that can be positioned between a ligand-derived warhead and an E3-recruiting element. The two terminal amide handles enable controlled conjugation chemistry (e.g., via activated carboxyl or amide coupling strategies) to generate symmetrical or appropriately spaced bifunctional architectures, while the PEG segments help tune solubility, reduce nonspecific hydrophobic interactions, and mitigate steric clashes that can impair ternary complex formation. In PROTAC design, such linkers are critical for optimizing the geometric relationship between binding domains, thereby supporting efficient recruitment of the target protein to the E3 ligase. This linker is valuable for researchers seeking reproducible linker length and flexibility to systematically evaluate degradation potency and selectivity.

Structure of 2353409-77-3

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Molecular Formula

C₄₂H₈₂N₂O₂₂

Molecular Weight

967.10

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

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Please store the product under the recommended conditions in the Certificate of Analysis.

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Room temperature in continental US; may vary elsewhere.

IUPACName

(2S)-2,6-bis[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxycarbonylamino]hexanoic acid

InChI Key

ZWXXNJUHFRYALT-KDXMTYKHSA-N

InChI

InChI=1S/C42H82N2O22/c1-49-7-9-51-11-13-53-15-17-55-19-21-57-23-25-59-27-29-61-31-33-63-35-37-65-41(47)43-6-4-3-5-39(40(45)46)44-42(48)66-38-36-64-34-32-62-30-28-60-26-24-58-22-20-56-18-16-54-14-12-52-10-8-50-2/h39H,3-38H2,1-2H3,(H,43,47)(H,44,48)(H,45,46)/t39-/m0/s1

SMILES

COCCOCCOCCOCCOCCOCCOCCOCCOC(=O)NCCCCC(C(=O)O)NC(=O)OCCOCCOCCOCCOCCOCCOCCOCCOC

1. Data on synthesis of oligomeric and polymeric poly(butylene adipate-co-butylene terephthalate) model substrates for the investigation of enzymatic hydrolysis

Veronika Perz, Klaus Bleymaier, Carsten Sinkel, Ulf Kueper, Melanie Bonnekessel, Doris Ribitsch, Georg M Guebitz Data Brief. 2016 Feb 19;7:291-8.doi: 10.1016/j.dib.2016.02.029.eCollection 2016 Jun.

The aliphatic-aromatic copolyester poly(butylene adipate-co-butylene terephthalate) (PBAT), also known as ecoflex, contains adipic acid, 1,4-butanediol and terephthalic acid and is proven to be compostable [1], [2], [3]). We describe here data for the synthesis and analysis of poly(butylene adipate-co-butylene terephthalate variants with different adipic acid:terephatalic acid ratios and 6 oligomeric PBAT model substrates. Data for the synthesis of the following oligomeric model substrates are described: mono(4-hydroxybutyl) terephthalate (BTa), bis(4-(hexanoyloxy)butyl) terephthalate (HaBTaBHa), bis(4-(decanoyloxy)butyl) terephthalate (DaBTaBDa), bis(4-(tetradecanoyloxy)butyl) terephthalate (TdaBTaBTda), bis(4-hydroxyhexyl) terephthalate (HTaH) and bis(4-(benzoyloxy)butyl) terephthalate (BaBTaBBa). Polymeric PBAT variants were synthesized with adipic acid:terephatalic acid ratios of 100:0, 90:10, 80:20, 70:30, 60:40 and 50:50. These polymeric and oligomeric substances were used as ecoflex model substrates in enzymatic hydrolysis experiments in the article "Substrate specificities of cutinases on aliphatic-aromatic polyesters and on their model substrates" [4].

2. Facile synthesis of insulin fusion derivatives through sortase A ligation

Maria M Disotuar, Jake A Smith, Jinze Li, Steve Alam, Nai-Pin Lin, Danny Hung-Chieh Chou Acta Pharm Sin B. 2021 Sep;11(9):2719-2725.doi: 10.1016/j.apsb.2020.11.011.Epub 2020 Nov 21.

Insulin derivatives such as insulin detemir and insulin degludec are U.S. Food and Drug Administration (FDA)-approved long-acting insulin currently used by millions of people with diabetes. These derivatives are modified in C-terminal B29 lysine to retain insulin bioactivity. New and efficient methods for facile synthesis of insulin derivatives may lead to new discovery of therapeutic insulin. Herein, we report a new method using sortase A (SrtA)-mediated ligation for the synthesis of insulin derivatives with high efficiency and functional group tolerance in the C-terminal B chain. This new insulin molecule (Ins-SA) with an SrtA-recognizing motif can be conjugated to diverse groups with N-terminal oligoglycines to generate new insulin derivatives. We further demonstrated that a new insulin derivative synthesized by this SrtA-mediated ligation shows strong cellular and in vivo bioactivity. This enzymatic method can therefore be used for future insulin design and development.

3. Manganese-Catalyzed Regioselective C-H Lactonization and Hydroxylation of Fatty Acids with H2O2

Vladimir I Kurganskiy, Roman V Ottenbacher, Mikhail V Shashkov, Evgenii P Talsi, Denis G Samsonenko, Konstantin P Bryliakov Org Lett. 2022 Dec 9;24(48):8764-8768.doi: 10.1021/acs.orglett.2c03458.Epub 2022 Nov 30.

Herein, we report the direct selective C-H lactonization of fatty acids (C5-C16), catalyzed by manganese(II) complexes bearing bis-amino-bis-pyridine ligands. The catalyst system uses the environmentally benign hydrogen peroxide as oxidant and exhibits high efficiency (100-200 TON), providing under optimized conditions γ-lactones in 60-90% yields. Remarkably, by changing the reaction conditions, the oxidation of hexanoic acid can be diverted toward formation of δ-caprolactone in up to 67% yield. Furthermore, the possibility of obtaining (ω-1)-hydroxy derivatives from linear C7-C10 acids in up to 48% yields has been demonstrated.

Bis-(m-PEG8-amido)-hexanoic acid can be used as a flexible, water-compatible spacer with multiple PEG-derived functional groups for modular conjugation workflows. Its poly(ethylene glycol) character helps tune solubility and conformational freedom, which are key considerations in targeted protein degradation workflows. The sections below describe its structural features and practical reactivity for linker installation in PROTAC constructs.

Structure: The molecule contains a hexanoic acid core bearing two m-PEG8 substituents through carbamate linkages. It features one carboxylic acid, two carbamate groups, and ether-rich PEG segments that confer hydrophilicity. The carbamate carbonyls and ether oxygen atoms provide polar functionality while retaining flexible chain conformations.

Reactivity: The carboxylic acid group is typically used for coupling to PROTAC warheads or E3 ligase ligands via standard amide-forming strategies. Common approaches include activation of the acid (for example, using carbodiimides or uronium-type reagents) followed by nucleophilic attack by an amine on the partner ligand. Reactions are generally performed in polar aprotic or mixed aqueous media under conditions that preserve carbamate integrity and minimize PEG-related side reactions.

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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