Biotin-XX-NHS

• CAS: 89889-52-1
• Catalog Number: ACM89889521
• Category: Main Products
• Molecular Weight: 567.7g/mol
• Molecular Formula: C26H41N5O7S
• Synonyms: (+)-Biotin-LC-LC-NHS Ester
• IUPAC Name: (2,5-dioxopyrrolidin-1-yl) 6-[6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoylamino]hexanoate
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCCCNC(=O)CCCCC2C3C(CS2)NC(=O)N3
• InChI: InChI=1S/C26H41N5O7S/c32-20(27-16-8-2-4-12-24(36)38-31-22(34)13-14-23(31)35)10-3-1-7-15-28-21(33)11-6-5-9-19-25-18(17-39-19)29-26(37)30-25/h18-19,25H,1-17H2,(H,27,32)(H,28,33)(H2,29,30,37)/t18-,19-,25-/m0/s1
• InChI Key: ATYCFNRXENKXSE-MHPIHPPYSA-N
• Appearance: White Powder
• Complexity: 886
• Covalently-Bonded Unit Count: 1
• Exact Mass: 567.27267g/mol
• Formal Charge: 0
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Heavy Atom Count: 39
• Monoisotopic Mass: 567.27267g/mol
• Rotatable Bond Count: 19
• XLogP3: 0.4

Case Study

Biotin-XX-NHS as an Amine-Reactive Biotinylation Reagent for Protein Functionalization on Electrospun Fibers

Kumar, Manish, et al. Journal of Biomedical Materials Research Part A 105.2 (2017): 356-362.

The avidin-biotin interaction is one of the strongest non-covalent bonds in nature, widely exploited for biosensor development, diagnostic assays, and biomolecule immobilization. This study employed Biotin-XX-NHS (biotinamidohexanoyl-6-aminohexanoic acid N-hydroxysuccinimide ester) as a heterobifunctional reagent for covalent biotinylation of bovine serum albumin (BSA), enabling its incorporation into electrospun polylactic acid-polyethylene glycol (PLA-PEG) fibers.
Biotin-XX-NHS features an extended spacer arm that reduces steric hindrance and improves biotin accessibility. The NHS ester reacts selectively with primary amines on BSA under mild aqueous conditions (pH 7), forming stable amide bonds. Biotinylated BSA was then blended with PLA-PEG in chloroform and electrospun into uniform fibers.
Key Results: Successful biotinylation of BSA was achieved using Biotin-XX-NHS (25 mg in DMF added to 2.95 g BSA in phosphate buffer), with excess reagent removed by dialysis. Biotinylated BSA incorporated into PLA-PEG fibers (0.01 wt%) enabled specific immobilization of fluorescently labeled avidin, as confirmed by confocal microscopy-avidin binding was observed only on biotin-containing fibers and was completely blocked by excess free biotin.
Enzymatic assays using streptavidin-alkaline phosphatase demonstrated biotin-specific enzyme immobilization, with clear chromogenic signal (absorbance at 405 nm) only on biotinylated fibers, confirming retained bioactivity and accessibility.

Biotin-XX-NHS as an Amine-Reactive Biotinylation Reagent for Biosensor Surface Functionalization

Konopsky, Valery N., et al. Sensors 13.2 (2013): 2566-2578.

Label-free optical biosensors enable real-time monitoring of biomolecular interactions without fluorescent tags. The biotin-streptavidin system offers exceptional binding affinity, yet efficient immobilization of biotin groups on sensor surfaces requires reliable conjugation chemistry. In this study, Biotin-XX-NHS (biotinamidohexanoyl-6-aminohexanoic acid N-hydroxysuccinimide ester) was employed as a heterobifunctional reagent for covalent biotinylation of sensor surfaces in a photonic crystal surface wave (PC SW) biosensor platform.
The sensor surface (SiO2) was first functionalized with aminopropyl triethoxysilane (APTES) to introduce primary amine groups. Biotin-XX-NHS, featuring an extended spacer arm to reduce steric hindrance, was then reacted with the amine-terminated surface via its NHS ester moiety, forming stable amide bonds. This created a biotinylated interface for subsequent capture of streptavidin and detection of biotin binding.
Key Results: Successful surface biotinylation was achieved using Biotin-XX-NHS (500 μg/mL in DMF, overnight incubation), enabling specific immobilization of streptavidin (12 μg/mL) as monitored in real-time by the PC SW biosensor. The biotinylated surface supported detection of free biotin (244 Da) binding to the streptavidin monolayer, with the sensor reliably resolving adlayer thickness changes (~0.35 nm) from bulk refractive index variations-demonstrating the ability to segregate surface and volume signals. The extended spacer arm of Biotin-XX-NHS improved biotin accessibility, contributing to stable streptavidin capture and enabling sensitive detection of small-molecule binding events.

Custom Q&A

What is the molecular formula of Biotin-XX-NHS?

The molecular formula of Biotin-XX-NHS is C26H41N5O7S.

What is the synonym for Biotin-XX-NHS?

The synonym for Biotin-XX-NHS is Succinimidyl-6-[6-(biotinamido)caproyl]caproylate.

What is the molecular weight of Biotin-XX-NHS?

The molecular weight of Biotin-XX-NHS is 567.7 g/mol.

When was Biotin-XX-NHS created?

Biotin-XX-NHS was created on July 16, 2007.

What is the IUPAC name of Biotin-XX-NHS?

The IUPAC name of Biotin-XX-NHS is (2,5-dioxopyrrolidin-1-yl) 6-[6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoylamino]hexanoate.

What is the InChI of Biotin-XX-NHS?

The InChI of Biotin-XX-NHS is InChI=1S/C26H41N5O7S/c32-20(27-16-8-2-4-12-24(36)38-31-22(34)13-14-23(31)35)10-3-1-7-15-28-21(33)11-6-5-9-19-25-18(17-39-19)29-26(37)30-25/h18-19,25H,1-17H2,(H,27,32)(H,28,33)(H2,29,30,37)/t18-,19-,25-/m0/s1.

What is the InChIKey of Biotin-XX-NHS?

The InChIKey of Biotin-XX-NHS is ATYCFNRXENKXSE-MHPIHPPYSA-N.

What is the Canonical SMILES of Biotin-XX-NHS?

The Canonical SMILES of Biotin-XX-NHS is C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCCCNC(=O)CCCCC2C3C(CS2)NC(=O)N3.

What is the CAS number of Biotin-XX-NHS?

The CAS number of Biotin-XX-NHS is 89889-52-1.

What is the XLogP3-AA value of Biotin-XX-NHS?

The XLogP3-AA value of Biotin-XX-NHS is 0.4.