109276-34-8

Basic information

• Product Name: BIOTINAMIDOCAPROYL HYDRAZIDE
• Synonyms: N-biotinyl-6-aminocaproic hydrazide;(+)-Biotin-ε-aminocaproyl hydrazide, (+)-Biotin-X-hydrazide, (+)-Biotinamidocaproyl hydrazide, BACH, N-(+)-Biotinyl-6-aminohexanoic hydrazide;6-Bach;Hexanoic acid, 6-((5-((3as,4S,6ar)-hexahydro-2-oxo-1H-thieno(3,4-D)imidazol-4-yl)-1-oxopentyl)amino)-, hydrazide;Hexanoic acid, 6-((5-(hexahydro-2-oxo-1H-thieno(3,4-D)imidazol-4-yl)-1-oxopentyl)amino)-, hydrazide, (3as-(3aalpha,4beta,6aalpha))-;Biotin-LC-Hz;EZ-Link Biotin-LC-hydrazide;N-(+)-Biotinyl-6-aminohexanoic hydrazide
• CAS NO: 109276-34-8
• Molecular Formula: C₁₆H₂₉N₅O₃S
• Molecular Weight: 371.5
• Product Categories: Biotinylation Reagents;biotinyl
• Mol File: 109276-34-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 195-196°C
• Boiling Point: 777 °C at 760 mmHg
• Flash Point: 423.7 °C
• Appearance: /powder
• Density: 1.188 g/cm³
• Vapor Pressure: 4.43E-24mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: 2-8°C
• Solubility: DMSO: 25 mg/mL
• PKA: 13.26±0.35(Predicted)
• CAS DataBase Reference: BIOTINAMIDOCAPROYL HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BIOTINAMIDOCAPROYL HYDRAZIDE(109276-34-8)
• EPA Substance Registry System: BIOTINAMIDOCAPROYL HYDRAZIDE(109276-34-8)

Safety Data

• Safety Statements: 22-24/25
• F: 10-21
• Hazardous Substances Data: 109276-34-8(Hazardous Substances Data)

Usage

Description

This is a hydrazide-activated biotinylation reagent used to label glycoproteins, carbohydrate-containing compounds that have oxidizable sugars or aldehydes. Hydrazine moiety reacts with an aldehyde to form semi-permanent hydrazone bonds. The extended spacer arm helps to minimize steric hindrance.

Chemical Properties

mp 195°C

Uses

Biotinylation reagent with aminocaproic spacer for aldehyde groups (e.g., periodate-oxidized sugars) and carboxylic acids. Typically used for coupling to glycoproteins through the carbohydrate by hydrazone bond formation.

Purification Methods

Suspend the hydrazide in ice-water (100mg/mL), stand overnight at 4o, filter and dry the solid in a vacuum. Recrystallise it from isoPrOH. RF is 0.26 on SiO2 plate using CHCl3/MeOH (7:3) as eluent. [O'Shannessy et al. Anal Biochem 163 204 1987.]

InChI:InChI=1/C16H29N5O3S/c17-21-14(23)8-2-1-5-9-18-13(22)7-4-3-6-12-15-11(10-25-12)19-16(24)20-15/h11-12,15H,1-10,17H2,(H,18,22)(H,21,23)(H2,19,20,24)/t11-,12-,15-/m0/s1

Upstream product

• 35013-72-0 biotin N-Hydroxysuccinimide ester 
• 58-85-5 biotin 
• 72040-64-3 N-(+)-biotinyl-6-aminocaproic acid 

Relevant articles and documents

Design and synthesis of biotinylated cardiac glycosides for probing Nur77 protein inducting pathway

The orphan nuclear receptor Nur77 (also known as TR3 or nerve growth factor-induced clone B NGFI-B) functions as a nuclear transcription factor in the regulation of target gene expression and plays a critical role in the regulation of differentiation, proliferation, apoptosis, and survival of many different cell types. Recent studies demonstrate that Nur77 also involves many important physiological and pathological processes including cancer, inflammation and immunity, cardiovascular diseases, and bone diseases. Our previous studies showed that cardiac glycosides could induce the expression of Nur77 protein and its translocation from the nucleus to the cytoplasm and subsequent targeting to mitochondria, leading to apoptosis of cancer cells. In order to probe the Nur77 protein inducting pathway, we designed and synthesized a series of novel biotinylated cardiac glycosides from β-Antiarin and α-Antiarin, two typical cardiac glycosides from the plant of Antiaris toxicaria. The induction of Nur77 protein expression of these biotinylated cardiac glycosides and their inhibitory effects on NIH-H460 cancer cell proliferation were evaluated. Results displayed that some biotinylated cardiac glycosides could significantly induce the expression of Nur77 protein comparable with their parent compounds β-Antiarin and α-Antiarin. Also, their streptavidin binding activities were evaluated. Among them, biotinylated cardiac glycosides P4b and P5a exhibited significant effect on the induction of Nur77 expression along with high binding capacity with streptavidin, suggesting that they can be used as probes for probing Nur77 protein inducting pathway.