Biotin-PEG5-azide

Name: Biotin-PEG5-azide
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1163732-89-5

Cat No.: BP-500951

Purity: >97% 4.5

Biotin-PEG5-azide is a heterobifunctional PROTAC linker built from a biotin affinity handle connected through a short, flexible polyethylene glycol (PEG) spacer to an azide functional group. The PEG segment provides aqueous solubility and conformational flexibility, helping the biotin moiety and the azide-bearing terminus behave independently when conjugated to larger constructs. In targeted protein degradation workflows, the azide enables efficient bioorthogonal “click” coupling to complementary alkyne-bearing partners, allowing researchers to attach the linker to PROTAC scaffolds, reporter tags, or surface/streptavidin-based capture systems. The biotin group further supports affinity enrichment and detection of degradation reagents or intermediates using streptavidin or NeutrAvidin, facilitating optimization of linker placement and monitoring of conjugate integrity. This product is valuable for constructing degraders with traceable components and for streamlining experimental workflows that require rapid, specific conjugation and downstream pull-down assays.

Structure of 1163732-89-5

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Worldwide
Delivery

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Category

PROTAC Linker

Molecular Formula

C₂₂H₄₀N₆O₇S

Molecular Weight

532.65

Appearance

White Solid

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

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Capabilities & Facilities

Comprehensive PROTAC Platform
Scientific Expertise & Technical Support
Custom Synthesis & Design Service
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Popular Publications Citing BOC Sciences Products

Purity

>97%

Appearance

White Solid

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-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethyl]pentanamide

Synonyms

(+)-Biotin-PEG5-CH2CH2N3

InChI Key

MKXKDMBFPMTVAW-ZJOUEHCJSA-N

InChI

InChI=1S/C22H40N6O7S/c23-28-25-6-8-32-10-12-34-14-16-35-15-13-33-11-9-31-7-5-24-20(29)4-2-1-3-19-21-18(17-36-19)26-22(30)27-21/h18-19,21H,1-17H2,(H,24,29)(H2,26,27,30)/t18-,19-,21-/m0/s1

SMILES

C1C2C(C(S1)CCCCC(=O)NCCOCCOCCOCCOCCOCCN=[N+]=[N-])NC(=O)N2

1. Development of biotin-tagged near-infrared fluorescence probes for tumor-specific imaging

Hang Li, Xiuting Wang, Yinxing Miao, Qingzhu Liu, Ke Li, Jianguo Lin, Minhao Xie, Ling Qiu J Photochem Photobiol B. 2021 Apr;217:112172. doi: 10.1016/j.jphotobiol.2021.112172.Epub 2021 Mar 3.

Near-infrared (NIR) probes are applicable for tumor imaging due to deep tissue penetration and low background signal. And cyanine dyes with long emission wavelength are excellent fluorophores to develop NIR probes. However, the aggregation of cyanine dyes in aqueous solution reduces the utilization of light. To solve this problem, polyethylene glycol (PEG) was introduced into the probes to reduce their aggregation. In our work, two new NIR probes G1 and G2 were designed and prepared by conjugating the cyanine dye G0 with Biotin-PEG5-Azide. The conjugated biotin could enhance the target specificity of probes. And the photophysical and photochemical parameters demonstrated that G1 and G2 had a reduced aggregation tendency. In vitro fluorescence imaging proved that these two probes could be specifically taken up by HeLa cells, and in vivo imaging demonstrated that these two probes could specifically target tumors with large tumor-to-muscle (T/M) ratios. All these results indicated that G1 and G2 are promising NIR fluorescent contrast agents for tumor-specific imaging.

Biotin-PEG5-azide is a PEG-based bifunctional linker designed for modular PROTAC assembly, combining a biotin tag with an azide handle for efficient conjugation. Its flexible polyether chain supports productive spatial presentation of ligands, while the azide enables bioorthogonal coupling strategies commonly used to generate targeted protein degraders. The linker’s design facilitates reliable synthesis workflows and downstream characterization, and the detailed structure and reactivity considerations are provided below.

Structure: Biotin-PEG5-azide contains a biotin moiety connected through a polyethylene glycol segment to a terminal azide. The linker features ether linkages within the PEG backbone and an azide functional group suitable for click-type reactions. Overall, it is a polar, flexible conjugation scaffold with improved solubility relative to purely aromatic linkers.

Reactivity: The azide group is compatible with copper-catalyzed azide–alkyne cycloaddition or strain-promoted azide–alkyne cycloaddition, enabling attachment to alkyne-bearing PROTAC warheads or E3 ligase ligands. Typical coupling is performed under inert atmosphere with appropriate base and ligand-stabilized copper catalysts for the CuAAC route, or under mild conditions for SPAAC. Solvent systems that maintain solubility of both partners are commonly selected to drive efficient conjugation while preserving sensitive functional groups.

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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