N-(3-Aminopropyl)biotinamide trifluoroacetate

 CAS No.: 244760-26-7  Cat No.: BP-502142  Purity: >98% 4.5  

N-(3-Aminopropyl)biotinamide trifluoroacetate is a biotin-derived linker featuring a biotinamide headgroup connected through a three-carbon aminopropyl spacer, supplied as a trifluoroacetate salt to enhance handling and solubility. Structurally, it provides a primary amine for covalent coupling and a biotin moiety for strong, high-affinity binding to streptavidin or avidin, enabling orthogonal attachment strategies in PROTAC and related targeted degradation workflows. In PROTAC design, this type of linker can be used to tether or immobilize PROTAC components, facilitate purification and detection via biotin–avidin interactions, or support conjugation to affinity handles while preserving functional groups on the warhead and ligand-binding elements. Its utility lies in improving experimental throughput for synthesis, characterization, and pull-down assays, thereby supporting rigorous evaluation of ternary-complex formation and degradation potency in targeted protein degradation research.

N-(3-Aminopropyl)biotinamide trifluoroacetate

Structure of 244760-26-7

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PROTAC Linker
Molecular Formula
C15H25F3N4O4S
Molecular Weight
414.44
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<a href="/product/n-3-aminopropyl-biotinamide-cas-244760-25-6-459959.html">244760-25-6</a> (free base)

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

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Purity
>98%
Storage
Store at 2-8 °C
IUPACName
5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(3-aminopropyl)pentanamide;2,2,2-trifluoroacetic acid
Synonyms
N-(+)-Biotinyl-3-aminopropylammonium trifluoroacetate; Biotinyl-DAPr.TFA; N-(3-Aminopropyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide 2,2,2-trifluoroacetate; 1H-Thieno[3,4-d]imidazole-4-pentanamide, N-(3-aminopropyl)hexahydro-2-oxo-, (3aS,4S,6aR)-, 2,2,2-trifluoroacetate (1:1); 1H-Thieno[3,4-d]imidazole-4-pentanamide, N-(3-aminopropyl)hexahydro-2-oxo-, (3aS,4S,6aR)-, mono(trifluoroacetate)
InChI Key
XIFKYHZIURRTHB-SVMJMOIZSA-N
InChI
InChI=1S/C13H24N4O2S.C2HF3O2/c14-6-3-7-15-11(18)5-2-1-4-10-12-9(8-20-10)16-13(19)17-12;3-2(4,5)1(6)7/h9-10,12H,1-8,14H2,(H,15,18)(H2,16,17,19);(H,6,7)/t9-,10-,12-;/m0./s1
SMILES
C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCN)NC(=O)N2.C(=O)(C(F)(F)F)O

This biotin-based PROTAC linker reagent enables modular assembly of targeted protein degraders by providing a biotin-derived recognition handle alongside a primary amine for controlled conjugation chemistry. Its trifluoroacetate counterion supports convenient handling and salt formation, facilitating coupling strategies commonly used to connect ligands, linkers, and E3-recruiting motifs. The structural and reactivity features described below will be detailed to support experimental design and PROTAC construction.

Structure: The linker comprises a biotinamide framework bearing an N-(3-aminopropyl) substituent, with an amide linkage and a terminal primary amine. The trifluoroacetate forms an ionic salt with the amine, improving stability and solubility. The molecule contains heteroatoms suited for hydrogen bonding and bioconjugation.

Reactivity: The primary amine enables standard PROTAC linker formation via nucleophilic substitution or amide/urea coupling with activated carboxylic acids, NHS-esters, or isocyanates, typically under mild base conditions. The trifluoroacetate counterion can be removed or neutralized in situ to free the amine for coupling. Common solvents include polar aprotic media, and reactions are often conducted at controlled temperature to preserve sensitive functional groups and maintain coupling efficiency.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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