Biotin-PEG4-Picolyl azide

Name: Biotin-PEG4-Picolyl azide
Brand: BOC Sciences
Price: 348 USD
Availability: MadeToOrder

CAS No.: 2222687-71-8

Cat No.: BP-501289

Purity: ≥95% 4.5

Biotin-PEG4-Picolyl azide is a heterobifunctional PROTAC linker reagent combining a biotin handle with a polyethylene glycol spacer and a picolyl azide reactive group. Structurally, it features a PEG4 chain that provides aqueous solubility and conformational flexibility, helping to reduce steric interference between the two functional termini. The picolyl azide can be used for azide-based conjugation chemistry, enabling attachment to complementary partners such as alkyne-bearing ligands or other azide-reactive modules used in targeted protein degradation workflows. In PROTAC design, this type of linker is valuable as a modular “molecular bridge” that can position a targeting ligand or degrader moiety while simultaneously incorporating a biotin tag for downstream detection, enrichment, or affinity-based pull-down experiments. Researchers use such biotin–PEG linkers to streamline synthesis and characterization of degrader constructs, improve experimental traceability, and support mechanistic studies of ternary complex formation and cellular engagement.

Structure of 2222687-71-8

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Category

PROTAC Linker

Molecular Formula

C27H42N8O7S

Molecular Weight

622.74

Appearance

Colorless to Off-white Oil

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

Size	Price	Stock	Quantity
25 mg	$348	In stock

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Purity

≥95%

Appearance

Colorless to Off-white Oil

Storage

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

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-[2-[2-[3-[[6-(azidomethyl)pyridin-3-yl]amino]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethyl]pentanamide

Synonyms

Biotin picolyl azide

InChI Key

MIIHOWLWUTYJDT-FXSPECFOSA-N

InChI

InChI=1S/C27H42N8O7S/c28-35-31-18-20-5-6-21(17-30-20)32-25(37)7-9-39-11-13-41-15-16-42-14-12-40-10-8-29-24(36)4-2-1-3-23-26-22(19-43-23)33-27(38)34-26/h5-6,17,22-23,26H,1-4,7-16,18-19H2,(H,29,36)(H,32,37)(H2,33,34,38)/t22-,23-,26-/m0/s1

SMILES

C1C2C(C(S1)CCCCC(=O)NCCOCCOCCOCCOCCC(=O)NC3=CN=C(C=C3)CN=[N+]=[N-])NC(=O)N2

1. Decatungstate-photocatalysed C(sp3)-H azidation

Yen-Chu Lu, Shih-Chieh Kao, Julian G West Chem Commun (Camb). 2022 Apr 14;58(31):4869-4872.doi: 10.1039/d2cc00425a.

C-H Azidation is an increasingly important tool for bioconjugation, materials chemistry, and the synthesis of nitrogen-containing natural products. While several approaches have been developed, these often require exotic and energetic reagents, expensive photocatalysts, or both. Here we report a simple and general C-H azidation reaction using earth-abundant tetra-n-butylammonium decatungstate as a photocatalyst and commercial p-acetamidobenzenesulfonyl azide (p-ABSA) as the azide source. This system can azidate a variety of unactivated C(sp3)-H bonds in moderate to good yields and excellent turnover numbers. Preliminary mechanistic experiments implicate a radical mechanism proceeding VIA photo-hydrogen atom transfer (photo-HAT).

2. Azidation in the Difunctionalization of Olefins

Kai Wu, Yujie Liang, Ning Jiao Molecules. 2016 Mar 16;21(3):352.doi: 10.3390/molecules21030352.

Organic azides are key motifs in compounds of relevance to chemical biology, medicinal chemistry and materials science. In addition, they also serve as useful building blocks due to their remarkable reactivity. Therefore, the development of efficient protocols to synthesize these compounds is of great significance. This paper reviews the major applications and development of azidation in difunctionalization of olefins using azide reagents.

3. Cross-Correlated Motions in Azidolysozyme

Seyedeh Maryam Salehi, Markus Meuwly Molecules. 2022 Jan 27;27(3):839.doi: 10.3390/molecules27030839.

The changes in the local and global dynamics of azide-labelled lysozyme compared with that of the wild type protein are quantitatively assessed for all alanine residues along the polypeptide chain. Although attaching -N3 to alanine residues has been considered to be a minimally invasive change in the protein it is found that depending on the location of the alanine residue, the local and global changes in the dynamics differ. For Ala92, the change in the cross-correlated motions are minimal, whereas attaching -N3 to Ala90 leads to pronounced differences in the local and global correlations as quantified by the cross-correlation coefficients of the Cα atoms. We also demonstrate that the spectral region of the asymmetric azide stretch distinguishes between alanine attachment sites, whereas changes in the low frequency, far-infrared region are less characteristic.

Biotin-PEG4-Picolyl azide is a PEG-based PROTAC linker designed to connect biotin-derived targeting motifs to picolyl-anchored handles, enabling efficient assembly of targeted protein degraders. Its flexible polyethylene glycol segment supports favorable linker dynamics and solubility, while the azide functionality provides a robust conjugation site commonly used in click-style ligations. The following sections describe the linker’s structure and practical reactivity considerations for PROTAC construction.

Structure: The linker comprises a biotin-bearing terminus connected through a polyethylene glycol chain to a picolyl-derived azide. It contains ether linkages within the PEG segment, aromatic heterocycle character at the picolyl portion, and a terminal azide group. These features impart flexibility and improved aqueous compatibility.

Reactivity: The azide group is suited to copper-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne cycloaddition, enabling modular PROTAC synthesis with alkyne-bearing partners under mild conditions. Typical strategies use compatible solvents such as polar aprotic media or buffered aqueous systems, with copper catalysis requiring ligand and oxygen-aware handling to limit side reactions. The conjugation proceeds via formation of a triazole linkage, preserving linker integrity for subsequent degrader evaluation.

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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