TAMRA-PEG4-Alkyne

 CAS No.: 1225057-68-0  Cat No.: BP-501189  Purity: 90% 4.5  

TAMRA-PEG4-Alkyne is a bifunctional, fluorescent PROTAC linker featuring a tetramethylrhodamine (TAMRA) dye conjugated to a short polyethylene glycol (PEG) spacer terminating in a terminal alkyne. The PEG4 segment provides aqueous solubility and conformational flexibility, helping to reduce steric interference between the dye and the protein-binding or E3-ligase–recruiting modules. In targeted protein degradation workflows, this linker is used to append a clickable alkyne handle to PROTAC-related constructs, enabling copper-catalyzed azide–alkyne cycloaddition (CuAAC) with complementary azide-functional partners for modular assembly and post-synthetic labeling. TAMRA fluorescence facilitates monitoring of conjugation efficiency and tracking of labeled PROTAC species in biochemical assays, such as gel-based visualization or fluorescence readouts of binding and cellular uptake. Overall, it is valuable for mechanistic studies that require both chemical handle installation and sensitive detection of PROTAC intermediates or degradation-relevant probes.

TAMRA-PEG4-Alkyne

Structure of 1225057-68-0

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Category
PROTAC Linker
Molecular Formula
C₃₆H₄₁N₃O₈
Molecular Weight
643.73

* 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
2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]-5-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethylcarbamoyl]benzoate
Synonyms
2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]-5-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethylcarbamoyl]benzoate; 5-((3,6,9,12-tetraoxapentadec-14-yn-1-yl)carbamoyl)-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate
Excitation
553
Emission
575
InChI Key
WQEIEHQRZQLUSE-UHFFFAOYSA-N
InChI
InChI=1S/C36H41N3O8/c1-6-14-43-16-18-45-20-21-46-19-17-44-15-13-37-35(40)25-7-10-28(31(22-25)36(41)42)34-29-11-8-26(38(2)3)23-32(29)47-33-24-27(39(4)5)9-12-30(33)34/h1,7-12,22-24H,13-21H2,2-5H3,(H-,37,40,41,42)
SMILES
CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=C(C=C4)C(=O)NCCOCCOCCOCCOCC#C)C(=O)[O-]

TAMRA-PEG4-Alkyne is a bifunctional PROTAC linker reagent combining a TAMRA fluorophore for analytical visualization with a PEG-based spacer terminating in an alkyne handle for modular conjugation. Its flexible, hydrophilic PEG segment supports productive ternary-complex formation by reducing steric constraints, while the alkyne enables efficient attachment to targeting ligands or other PROTAC components. The following sections describe its structure and practical reactivity considerations in PROTAC assembly.

Structure: The linker comprises a TAMRA chromophore connected through a poly(ethylene glycol) spacer to a terminal alkyne. It contains aromatic and conjugated systems within TAMRA, ether linkages in the PEG chain, and a carbon–carbon triple bond at the reactive terminus, contributing to solubility and stable covalent functionality.

Reactivity: The terminal alkyne is suited for copper-catalyzed azide–alkyne cycloaddition (CuAAC) with azide-functional partners under standard click-chemistry conditions. This transformation proceeds via formation of a copper-acetylide intermediate followed by cycloaddition to yield a stable triazole linkage. Typical setups use a copper catalyst with an appropriate reducing agent and polar solvent systems compatible with biomolecule conjugation, enabling modular PROTAC construction and subsequent purification.

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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
g/mol
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