5-(Biotinamido)pentylamine TFA salt

 CAS No.: 288259-39-2  Cat No.: BP-502141  Purity: >97% 4.5  

5-(Biotinamido)pentylamine TFA salt is a biotin-derived primary amine linker featuring a biotinamide headgroup connected through a five-carbon spacer to an amino terminus, with trifluoroacetic acid forming a salt to improve handling and solubility. In PROTAC and targeted protein degradation designs, such biotinylated linkers are commonly used to introduce a high-affinity biotin handle that can be used to assemble ternary complexes or to conjugate biotin-binding modules, enabling controlled recruitment of biotin-recognizing partners while maintaining a defined linker length between functional domains. The flexible aliphatic chain and terminal amine support straightforward coupling to electrophilic groups (e.g., activated carboxylic acids or NHS-esters) to attach this linker to ligands, scaffolds, or reporter tags. As a modular building block, it facilitates systematic optimization of spatial arrangement and conjugation chemistry, which are critical determinants of degradation potency and selectivity in targeted protein degradation research.

5-(Biotinamido)pentylamine TFA salt

Structure of 288259-39-2

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PROTAC Linker
Molecular Formula
C17H29F3N4O4S
Molecular Weight
442.50
Related CAS
<a href="/product/5-biotinamido-pentylamine-cas-115416-38-1-117714.html">115416-38-1</a> (free base)

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

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Purity
>97%
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-(5-aminopentyl)pentanamide;2,2,2-trifluoroacetic acid
Synonyms
Biotin-DAPe.TFA; Biotinyl cadaverine TFA salt; Cadaverine-X-biotin TFA salt; N-(5-Aminopentyl)biotinamide trifluoroacetate; Biotinylated 1,5-diaminopentane TFA salt; Biotinyl-DAPe.TFA; 1H-Thieno[3,4-d]imidazole-4-pentanamide, N-(5-aminopentyl)hexahydro-2-oxo-, (3aS,4S,6aR)-, 2,2,2-trifluoroacetate (1:1); 1H-Thieno[3,4-d]imidazole-4-pentanamide, N-(5-aminopentyl)hexahydro-2-oxo-, (3aS,4S,6aR)-, mono(trifluoroacetate); N-(5-Aminopentyl)biotinamide trifluoroacetate salt; Biotin-cadaverin trifluoracetate; EZ-link Pentylamine-Biotin trifluoracetate; Pentylamine biotin trifluoracetate
InChI Key
QWKKJNXOPDNIEU-RGESYUBESA-N
InChI
InChI=1S/C15H28N4O2S.C2HF3O2/c16-8-4-1-5-9-17-13(20)7-3-2-6-12-14-11(10-22-12)18-15(21)19-14;3-2(4,5)1(6)7/h11-12,14H,1-10,16H2,(H,17,20)(H2,18,19,21);(H,6,7)/t11-,12-,14-;/m0./s1
SMILES
C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCCCN)NC(=O)N2.C(=O)(C(F)(F)F)O

This PROTAC linker, supplied as a trifluoroacetate (TFA) salt, provides a biotinamide-bearing, flexible aliphatic connection point suitable for assembling targeted protein degraders via modular conjugation. Its design supports reliable coupling to affinity ligands and receptor-binding modules while maintaining conformational freedom that can improve productive ternary complex formation. The detailed Structure and Reactivity parameters are provided below for experimental planning.

Structure: The linker contains a saturated, flexible pentyl chain terminating in a primary amine, paired with a biotinamide functionality. Amide and multiple hydrogen-bonding sites are present, while the TFA counterion forms an ionic salt with the amine. Overall, it is a polar, water-compatible organic linker.

Reactivity: The primary amine enables standard PROTAC assembly strategies such as amide-bond formation using activated carboxylic acids (e.g., NHS/activated esters) or coupling reagents commonly used for amine–carboxyl conjugation. Reaction conditions are typically mild and compatible with biotin derivatives, often employing polar aprotic solvents and base to promote nucleophilic acyl substitution. The TFA salt can be neutralized in situ to improve coupling efficiency.

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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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