N-(Azido-PEG3)-N-Biotin-PEG4-methyl ester

 CAS No.: 2100306-76-9  Cat No.: BP-501139  Purity: 98% 4.5  

N-(Azido-PEG3)-N-Biotin-PEG4-methyl ester is a heterobifunctional PEG-based linker that combines an azide handle with a biotin moiety and a terminal methyl ester. Structurally, it consists of an azido-terminated short polyethylene glycol segment connected to a biotin-conjugation region through an amide linkage, followed by a longer PEG4 spacer that improves aqueous solubility and spatial control. In PROTAC and targeted degradation workflows, the azide group enables bioorthogonal conjugation (e.g., copper-free click chemistry) to install the linker onto an E3 ligase ligand or other binding module, while the biotin functionality can be used for affinity-based capture, localization, or modular assembly with biotin-binding partners. The methyl ester provides a chemically addressable end group that can be leveraged for controlled derivatization or stability tuning during synthesis. This linker is valuable for constructing well-defined, water-compatible PROTAC architectures and for facilitating purification or analytical tracking of assembled conjugates.

N-(Azido-PEG3)-N-Biotin-PEG4-methyl ester

Structure of 2100306-76-9

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PROTAC Linker
Molecular Formula
C₃₀H₅₄N₆O₁₁S
Molecular Weight
706.85

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

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Purity
98%
Storage
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
methyl 3-[2-[2-[2-[2-[5-[(3aR,4R,6aS)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoyl-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
methyl 1-{5-[(3aR,4R,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]-N-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethyl)pentanamido}-3,6,9,12-tetraoxapentadecan-15-oate; methyl 1-azido-12-(5-((3aR,4R,6aS)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl)-3,6,9,15,18,21,24-heptaoxa-12-azaheptacosan-27-oate
InChI Key
ZZZFELOBFYPAJE-WWPJHQMMSA-N
InChI
InChI=1S/C30H54N6O11S/c1-40-28(38)6-10-41-14-18-45-22-23-47-21-17-44-13-9-36(8-12-43-16-20-46-19-15-42-11-7-32-35-31)27(37)5-3-2-4-26-29-25(24-48-26)33-30(39)34-29/h25-26,29H,2-24H2,1H3,(H2,33,34,39)/t25-,26-,29-/m1/s1
SMILES
COC(=O)CCOCCOCCOCCOCCN(CCOCCOCCOCCN=[N+]=[N-])C(=O)CCCCC1C2C(CS1)NC(=O)N2
1. Synthesis of New Cyclopeptide Analogues of the Miuraenamides
Sarah Kappler, Andreas Siebert, Uli Kazmaier Curr Org Synth. 2021;18(4):418-424.doi: 10.2174/1570179418666210113161550.
Introduction:Miuraenamides belong to natural marine compounds with interesting biological properties.Materials and methods:Miuraenamides initiate polymerization of monomeric actin and therefore show high cytotoxicity by influencing the cytoskeleton. New derivatives of the miuraenamides have been synthesized containing an N-methylated amide bond instead of the more easily hydrolysable ester in the natural products. Results:Incorporation of an aromatic side chain onto the C-terminal amino acid of the tripeptide fragment also led to highly active new miuraenamides.Conclusion:In this study, we showed that the ester bond of the natural product miuraenamide can be replaced by an N-methyl amide. The yields in the cyclization step were high and generally much better than with the corresponding esters. On the other hand, the biological activity of the new amide analogs was lower compared to the natural products, but the activity could significantly be increased by incorporation of a p-nitrophenyl group at the C-terminus of the peptide fragment.
2. Second-generation probes for biosynthetic intermediate capture: towards a comprehensive profiling of polyketide assembly
Ina Wilkening, Silvia Gazzola, Elena Riva, James S Parascandolo, Lijiang Song, Manuela Tosin Chem Commun (Camb). 2016 Aug 16;52(68):10392-5.doi: 10.1039/c6cc04681a.
Malonyl carba(dethia) N-decanoyl cysteamine methyl esters and novel acetoxymethyl esters were utilised as second-generation probes for polyketide intermediate capture. The use of these tools in vivo led to the characterisation of an almost complete set of biosynthetic intermediates from a modular assembly line, providing a first kinetic overview of intermediate processing leading to complex natural product formation.

This PROTAC linker reagent, N-(Azido-PEG3)-N-Biotin-PEG4-methyl ester, combines an azide handle with PEG-based spacing and a biotin motif to support modular assembly of targeted protein degraders. Its flexible polyethylene glycol segments can improve solubility and presentation of reactive termini, while the biotin functionality enables robust conjugation strategies commonly used in proximity-inducing designs. The following sections describe its structure and practical reactivity considerations for linker incorporation into PROTAC constructs.

Structure: The molecule is built from PEG oligomers featuring ether linkages that provide conformational flexibility and improved hydrophilicity. A terminal azide group enables bioorthogonal click chemistry, while a biotin-derived amide region and a methyl ester provide orthogonal functional handles for controlled conjugation and coupling.

Reactivity: The azide is typically used in copper-catalyzed azide–alkyne cycloaddition or related click reactions to join PROTAC fragments under mild, aqueous-compatible conditions. The methyl ester can undergo standard ester-activation or nucleophilic acyl substitution approaches to form amide or related linkages, depending on the coupling partner. Selection of solvent systems and catalysts should follow established click and ester-coupling protocols that preserve sensitive targeting ligands and maintain linker integrity.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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