N-(Azido-PEG4)-biocytin

Name: N-(Azido-PEG4)-biocytin
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 2055042-70-9

Cat No.: BP-501415 4.5

N-(Azido-PEG4)-biocytin is a PEG-based linker reagent that combines a biotin moiety with a terminal azide functionality separated by a short, flexible tetraethylene glycol (PEG4) chain. The azide group enables bioorthogonal conjugation via copper-free or copper-catalyzed azide–alkyne cycloaddition, allowing researchers to attach the linker to complementary handles such as propargyl-modified ligands, affinity tags, or PROTAC-related components. In PROTAC and targeted degradation workflows, this linker is valuable because the biotin terminus can be used for strong, noncovalent capture or immobilization on streptavidin/avidin matrices, facilitating purification, assay development, and multicomponent assembly strategies. The PEG spacer improves solubility and reduces steric interference, which can help preserve binding and ternary-complex formation when conjugating large or multifunctional degradation constructs. Overall, it provides a practical, modular platform for constructing and characterizing biotin-tagged or azide-reactive targeted degradation reagents.

Structure of 2055042-70-9

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Category

PROTAC Linker

Molecular Formula

C₂₇H₄₇N₇O₉S

Molecular Weight

645.77

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

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

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IUPACName

(2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-[3-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]propanoylamino]hexanoic acid

InChI Key

PGFHEZMNHBZACD-UEOMBKFZSA-N

InChI

InChI=1S/C27H47N7O9S/c28-34-30-10-12-41-14-16-43-18-17-42-15-13-40-11-8-24(36)31-20(26(37)38)5-3-4-9-29-23(35)7-2-1-6-22-25-21(19-44-22)32-27(39)33-25/h20-22,25H,1-19H2,(H,29,35)(H,31,36)(H,37,38)(H2,32,33,39)/t20-,21-,22-,25-/m0/s1

SMILES

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

1. Advances and perspectives in tissue clearing using CLARITY

Kristian H Reveles Jensen, Rune W Berg J Chem Neuroanat. 2017 Dec;86:19-34.doi: 10.1016/j.jchemneu.2017.07.005.Epub 2017 Jul 17.

CLARITY is a tissue clearing method, which enables immunostaining and imaging of large volumes for 3D-reconstruction. The method was initially time-consuming, expensive and relied on electrophoresis to remove lipids to make the tissue transparent. Since then several improvements and simplifications have emerged, such as passive clearing (PACT) and methods to improve tissue staining. Here, we review advances and compare current applications with the aim of highlighting needed improvements as well as aiding selection of the specific protocol for use in future investigations.

2. Determination of biocytin

H Ebrahim, K Dakshinamurti Anal Biochem. 1987 May 1;162(2):319-24.doi: 10.1016/0003-2697(87)90398-8.

Biocytin (epsilon-N-[d-biotinyl]-L-lysine) is generally undetected in serum and other body fluids of normal healthy individuals in view of the ubiquitous distribution of biotinidase. It has been suggested that biocytin may be present in serum and urine of patients with inherited biotinidase deficiency. We have developed a noncompetitive assay for biocytin based on its interaction with avidin. Biocytin can be determined in biological samples containing both biotin and biocytin. Biotin from such samples is removed by an anion-exchange resin and the biocytin is determined by the avidin-binding assay. The effect of above-normal levels of biotin in the sample on the assay of biocytin is discussed.

3. 3-(N-Maleimido-propionyl)biocytin: a versatile thiol-specific biotinylating reagent

E A Bayer, M G Zalis, M Wilchek Anal Biochem. 1985 Sep;149(2):529-36.doi: 10.1016/0003-2697(85)90609-8.

A biotin-containing, thiol-specific reagent, 3-(N-maleimido-propionyl) biocytin (MPB), was synthesized and used to biotinylate various proteins via native or artificially induced sulfhydryl groups. In combination with appropriate avidin- or streptavidin-conjugated markers (i.e., fluorescent, enzyme-conjugated, electron-dense, etc.), MPB essentially constitutes a universal, multipurpose, thiol-specific probe. The reagent could be used to detect protein SH groups on dot blots with sensitivities in the femtomole range. The labeling was very specific for sulfhydryl groups or reduced S-S bonds; proteins lacking free SH groups were unlabeled by this method. Due to the long spacer between the biotinyl group and the reactive maleimide, improved adsorption of biotinylated proteins to avidin columns was achieved. An SH-containing enzyme (beta-galactosidase) was biotinylated with MPB, and the resultant biotinylated enzyme could be used as an efficient histochemical probe. The use of this reagent is recommended to biotinylate proteins which contain nonessential SH groups or which can be easily thiolylated prior to reaction with MPB.

N-(Azido-PEG4)-biocytin is a PEG-based linker bearing an azide handle for modular conjugation in targeted protein degradation workflows. Its flexible poly(ethylene glycol) segment supports productive spatial presentation of ligands, while the azide enables chemoselective “click” coupling to complementary alkynes for assembling PROTACs. The resulting conjugates can be generated under mild conditions with high functional-group tolerance; detailed structural and reactivity considerations are provided below.

Structure: The linker comprises a biotin-derived scaffold connected through an ether-rich PEG chain, terminating in an azide functional group. It contains stable amide and ether linkages, with an azide moiety suitable for bioorthogonal reactions. The PEG segment confers conformational flexibility and improved solubility in aqueous media.

Reactivity: The azide group is designed for copper-catalyzed azide–alkyne cycloaddition or copper-free strain-promoted azide–alkyne cycloaddition, enabling efficient formation of triazole-linked PROTAC architectures. Typical coupling proceeds under mild, ligand-compatible conditions using an appropriate alkyne partner, with solvent systems that support both reactant solubility and reaction kinetics. Reaction efficiency depends on maintaining azide integrity and minimizing side reactions during conjugation.

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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