Diazo Biotin-PEG3-azide

Name: Diazo Biotin-PEG3-azide
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1339202-33-3

Cat No.: BP-501236 4.5

Diazo Biotin-PEG3-azide is a heterobifunctional PEG-based linker that combines an azo-containing cleavable biotin tag with a terminal azide for orthogonal “click” coupling to alkyne-bearing partners. Structurally, it features a short three-unit polyethylene glycol spacer that provides aqueous solubility and spatial separation between the biotin moiety and the reactive termini, while the azo linker can be reductively cleaved (for example, with sodium dithionite) to release captured biotinylated material. In targeted protein degradation workflows, this linker can be used to functionalize PROTAC-related components or auxiliary ligands, enabling controlled attachment to alkyne-bearing handles (e.g., via CuAAC with terminal alkynes or SPAAC with strained cyclooctynes) and facilitating purification or detection through streptavidin affinity. Its value lies in providing modular, experimentally convenient conjugation chemistry for building well-defined degraders and for monitoring synthesis, localization, or pull-down of ternary-complex–associated material.

Structure of 1339202-33-3

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Category

PROTAC Linker

Molecular Formula

C₃₃H₄₅N₉O₇S

Molecular Weight

711.83

* 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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IUPACName

N-[2-[2-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethoxy]ethoxy]ethoxy]ethyl]-4-[[5-(2-azidoethyl)-2-hydroxyphenyl]diazenyl]benzamide

InChI Key

VQJUOWXTLWKWGJ-JLHXZSQLSA-N

InChI

InChI=1S/C33H45N9O7S/c34-42-37-12-11-23-5-10-28(43)26(21-23)41-40-25-8-6-24(7-9-25)32(45)36-14-16-48-18-20-49-19-17-47-15-13-35-30(44)4-2-1-3-29-31-27(22-50-29)38-33(46)39-31/h5-10,21,27,29,31,43H,1-4,11-20,22H2,(H,35,44)(H,36,45)(H2,38,39,46)/t27-,29-,31-/m0/s1

SMILES

C1C2C(C(S1)CCCCC(=O)NCCOCCOCCOCCNC(=O)C3=CC=C(C=C3)N=NC4=C(C=CC(=C4)CCN=[N+]=[N-])O)NC(=O)N2

1. Imidazole-1-sulfonyl azide-based diazo-transfer reaction for the preparation of azido solid supports for solid-phase synthesis

Vida Castro, Juan B Blanco-Canosa, Hortensia Rodriguez, Fernando Albericio ACS Comb Sci. 2013 Jul 8;15(7):331-4.doi: 10.1021/co4000437.Epub 2013 Jun 6.

An efficient, standard, mild, and copper-free imidazole-1-sulfonyl azide hydrochloride-based diazo-transfer method was implemented in a set of four resins that cover a broad range of hydrophobicity. The imidazole-1-sulfonyl azide hydrochloride is easily prepared/commercially available, stable upon storage at 4 °C, and proved to be a suitable alternative to triflyl azide for diazo-transfer reactions in amine functionalized resins. We have successfully applied the azido resins for the conjugation of a TFA-labile Wang-type linker using Click Chemistry.

2. Taming tosyl azide: the development of a scalable continuous diazo transfer process

Benjamin J Deadman, Rosella M O'Mahony, Denis Lynch, Daniel C Crowley, Stuart G Collins, Anita R Maguire Org Biomol Chem. 2016 Apr 7;14(13):3423-31.doi: 10.1039/c6ob00246c.Epub 2016 Mar 9.

Heat and shock sensitive tosyl azide was generated and used on demand in a telescoped diazo transfer process. Small quantities of tosyl azide were accessed in a 'one pot' batch procedure using shelf stable, readily available reagents. For large scale diazo transfer reactions tosyl azide was generated and used in a telescoped flow process, to mitigate the risks associated with handling potentially explosive reagents on scale. The in situ formed tosyl azide was used to rapidly perform diazo transfer to a range of acceptors, including β-ketoesters, β-ketoamides, malonate esters and β-ketosulfones. An effective in-line quench of sulfonyl azides was also developed, whereby a sacrificial acceptor molecule ensured complete consumption of any residual hazardous diazo transfer reagent. The telescoped diazo transfer process with in-line quenching was used to safely prepare over 21 g of an α-diazocarbonyl in >98% purity without any column chromatography.

3. A 'sulfonyl-azide-free' (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis

Dmitry Dar'in, Grigory Kantin, Mikhail Krasavin Chem Commun (Camb). 2019 May 8;55(36):5239-5242.doi: 10.1039/c9cc02042j.Epub 2019 Apr 15.

Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first 'sulfonyl-azide-free' (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution via combinatorial chemistry and a range of scaffold-generating transformations.

Diazo Biotin-PEG3-azide is a bifunctional PEG-based linker designed for modular PROTAC construction, containing an aryl azo linkage together with an azide group for orthogonal “click” conjugation. Its polyethylene glycol segment supports solubility and conformational flexibility, while the biotin motif enables convenient tagging and affinity-based workflows during synthesis and characterization. The following sections describe the linker’s structure and the practical reactivity considerations for assembling PROTAC intermediates.

Structure: The molecule contains a PEG3 hydrophilic spacer linked to an azide functionality and an aryl azo (–N=N–) moiety, together with a biotin-derived recognition element. It features ether linkages within the PEG chain and an azide group suitable for cycloaddition, alongside an aryl azo linkage that is distinct from a carbene-forming diazo group.

Reactivity: The azide group is well suited to copper-catalyzed or strain-promoted azide–alkyne cycloaddition, while the aryl azo unit should not be treated as a diazo carbene precursor. For PROTAC assembly, click conjugation at the azide can be performed with an appropriate alkyne partner under conditions compatible with the azo-containing scaffold. Reaction media and catalysts should be chosen to preserve protein-binding integrity and minimize 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