N-(3-Aminopropyl)biotinamide

 CAS No.: 244760-25-6  Cat No.: BP-502143  Purity: >98% 4.5  

N-(3-Aminopropyl)biotinamide is a biotin-derived linker bearing a primary amine at the terminus of a short three-carbon spacer, enabling robust covalent coupling to amine-reactive or activated carboxyl groups on PROTAC-related ligands and other functional modules. Structurally, it combines the high-affinity biotin motif with a flexible aminopropyl chain, providing both a handle for conjugation chemistry and a spatially defined separation between the biotin moiety and the attachment point. In targeted protein degradation workflows, such linkers are commonly used to generate biotinylated intermediates that can be further functionalized for assembling bifunctional degraders, including strategies where biotin serves as a modular tag for affinity-based capture, localization, or purification of PROTAC constructs. Its value for research lies in facilitating controlled, modular synthesis of conjugates, improving reproducibility of linker attachment, and supporting downstream analytical workflows such as affinity enrichment and characterization of degradation reagents.

N-(3-Aminopropyl)biotinamide

Structure of 244760-25-6

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PROTAC Linker
Molecular Formula
C13H24N4O2S
Molecular Weight
300.42
Related CAS
<a href="/product/n-3-aminopropyl-biotinamide-cas-244760-26-7-101392.html">244760-26-7</a> (TFA salt)

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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
Synonyms
(3aS,4S,6aR)-N-(3-Aminopropyl)hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide; N-(3-Aminopropyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide; N-Biotinyl-1,3-propanediamine; N-(+)-Biotinyl-3-aminopropylamine; Biotinyl-DAPr
Boiling Point
644.5±50.0 °C at 760 mmHg
Density
1.168±0.06 g/cm3
InChI Key
LKPUEUXUOQHTRS-NHCYSSNCSA-N
InChI
InChI=1S/C13H24N4O2S/c14-6-3-7-15-11(18)5-2-1-4-10-12-9(8-20-10)16-13(19)17-12/h9-10,12H,1-8,14H2,(H,15,18)(H2,16,17,19)/t9-,10-,12-/m0/s1
SMILES
C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCN)NC(=O)N2

N-(3-Aminopropyl)biotinamide is a biotin-based linker building block designed to connect biotin-derived targeting ligands to protein-binding or E3-recruiting modules in PROTAC architectures. Its biotin functionality supports strong, widely used affinity interactions, while the pendant aminopropyl group provides a practical handle for conjugation chemistry. Together, these features facilitate modular synthesis and optimization of targeted protein degradation constructs. The detailed structural and reactivity considerations for PROTAC assembly are provided below.

Structure: The molecule contains a biotinamide core linked to an aminopropyl substituent. It features amide and amine functionalities capable of hydrogen bonding and salt formation, with multiple heteroatoms that influence polarity and aqueous solubility. These characteristics make it suitable for bioconjugation workflows.

Reactivity: The aminopropyl group is typically used for coupling reactions to form stable amide or urea linkages with activated carboxylic acids or isocyanates. Common approaches include carbodiimide-mediated amide formation or activated ester chemistry under mild, anhydrous or buffered conditions, often using bases to maintain nucleophilicity. Reaction design should consider compatibility with other PROTAC components and the preservation of biotin’s binding-relevant functionality.

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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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