Biotin hydrazide

• CAS: 66640-86-6
• Catalog Number: ACM66640866
• Category: Other Products
• Molecular Weight: 258.3 g/mol
• Molecular Formula: C10H18N4O2S
• Description: Biotin hydrazide is a biotinyl derivative that can be used as a probe for the determination of protein carbonylation, which is a component of several diseases. Protein carbonylation, an irreversible post translational modification (PTM), is caused by attack of reactive oxygen species (ROS), numerous lipid oxidation products (such as α,β-unsaturated γ-hydroxyalkenals), or nonemzymatic glycation resulting in the loss of protein function. Biotin hydrazide is a preferred carbonyl-reactive probe for its direct reaction and chemistry and no requirement of additional catalysts or reducing agents. Biotin hydrazide exclusively and readily derivatizes carbonyl groups at pH 5.5, which facilitates its use to measure carbonylated proteins in biological samples.
• Synonyms: (+)-Biotin Hydrazide; Biotin-Hz; Hydrazide Biotin; Biotine Hydrazide
• IUPAC Name: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanehydrazide
• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)NN)NC(=O)N2
• InChI Key: KOZWHQPRAOJMBN-ZKWXMUAHSA-N
• Boiling Point: 633.1ºC at 760 mmHg
• Melting Point: 245-247ºC
• Flash Point: 336.7ºC
• Density: 1.243 g/cm³
• Appearance: white or slightly yellow powder
• Storage: Store at -20°C
• EC Number: 613-970-0
• Exact Mass: 258.11500
• H-Bond Acceptor: 3
• H-Bond Donor: 4
• Shipping: Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
• WGK Germany: 3

Synthetic Use

Upstream Synthesis Route 1

• 91853-90-6

• 66640-86-6

Reference: [1] Bioconjugate Chemistry, 2010, vol. 21, # 5, p. 979 - 987
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 19, p. 4689 - 4693

Upstream Synthesis Route 2

• 608-16-2

• 66640-86-6

Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18140 - 18148
[2] Journal of Biological Chemistry, 1942, vol. 144, p. 513,516

Upstream Synthesis Route 3

• 58-85-5

• 66640-86-6

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 19, p. 4689 - 4693
[2] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18140 - 18148

Upstream Synthesis Route 4

• 608-16-2

• 66640-86-6

Reference: [1]Journal of the American Chemical Society,2014,vol. 136,p. 18140 - 18148
[2]Journal of Biological Chemistry,1942,vol. 144,p. 513,516
[3]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 707 - 712