TAMRA-PEG3-Azide

 CAS No.: 1228100-59-1  Cat No.: BP-501474  Purity: 90% 4.5  

TAMRA-PEG3-Azide is a bifunctional, fluorescent PROTAC linker that combines a TAMRA (tetramethylrhodamine) reporting group with a short, flexible triethylene glycol (PEG3) spacer terminating in an azide handle. Structurally, the molecule provides a hydrophilic, conformationally mobile tether that can reduce steric interference between a targeting ligand and an E3-recruiting or reactive partner, while the azide enables efficient bioorthogonal conjugation (most commonly via copper-free azide–alkyne cycloaddition) to install the linker onto complementary modules. In targeted protein degradation workflows, this reagent is particularly valuable for building and validating degraders or related conjugates where tracking of localization, cellular uptake, or ternary-complex formation is required. The TAMRA label supports sensitive fluorescence readouts without substantially increasing hydrophobicity, and the PEG3 length helps maintain functional group accessibility, making it useful for optimizing linker geometry and experimentally comparing degradation-relevant conjugate designs.

TAMRA-PEG3-Azide

Structure of 1228100-59-1

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Category
PROTAC Linker
Molecular Formula
C₃₃H₃₈N₆O₇
Molecular Weight
630.69

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

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Purity
90%
Solubility
Water, DMSO, DMF, DCM
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-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethylcarbamoyl]-2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]benzoate
Synonyms
TAMRA-PEG3-N3; 5-Carboxytetramethylrhodamine-PEG3-Azide; 5-((2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)carbamoyl)-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate; 5-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethylcarbamoyl]-2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]benzoate; Xanthylium, 9-[4-(13-azido-1-oxo-5,8,11-trioxa-2-azatridec-1-yl)-2-carboxyphenyl]-3,6-bis(dimethylamino)-, inner salt
Excitation
553
Emission
575
InChI Key
YREJCORUQQJQHB-UHFFFAOYSA-N
InChI
InChI=1S/C33H38N6O7/c1-38(2)23-6-9-26-29(20-23)46-30-21-24(39(3)4)7-10-27(30)31(26)25-8-5-22(19-28(25)33(41)42)32(40)35-11-13-43-15-17-45-18-16-44-14-12-36-37-34/h5-10,19-21H,11-18H2,1-4H3,(H-,35,40,41,42)
SMILES
CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=C(C=C4)C(=O)NCCOCCOCCOCCN=[N+]=[N-])C(=O)[O-]

TAMRA-PEG3-Azide is a fluorescent, polyethylene glycol–containing azide linker designed for modular PROTAC assembly and analytical tracking. Its PEG segment provides aqueous compatibility and conformational flexibility, while the TAMRA fluorophore enables visualization of conjugation efficiency and localization in biochemical workflows. The terminal azide supports bioorthogonal click coupling to complementary alkynes, facilitating efficient construction of targeted protein degraders. The structure and reactivity considerations are described in detail below.

Structure: The linker contains a TAMRA fluorophore conjugated to a short PEG chain terminating in an azide functional group. It features ether linkages within the PEG segment, aromatic and heteroatom-rich motifs in the dye, and a terminal azide suitable for selective cycloaddition. Overall, it is designed for water-compatible handling.

Reactivity: The azide reacts selectively with terminal alkynes via copper-catalyzed azide–alkyne cycloaddition or, where required, copper-free strain-promoted variants. For PROTAC synthesis, the linker is typically coupled under mild conditions that preserve sensitive ligands and maintain fluorophore integrity. Common choices include polar organic/aqueous solvent mixtures, with catalysts such as Cu(I) generated in situ, or ligand-stabilized copper systems to control reactivity and minimize side reactions.

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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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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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