Biotinamidocaproyl hydrazide

Base Information

• Chemical Name: Biotinamidocaproyl hydrazide
• CAS No.: 109276-34-8
• Molecular Formula: C16H29 N5 O3 S
• Molecular Weight: 371.4982
• Hs Code.: 29349990
• European Community (EC) Number: 600-909-8
• DSSTox Substance ID: DTXSID80911069
• Nikkaji Number: J645.131D
• Wikidata: Q72443568
• ChEMBL ID: CHEMBL4439291
• Mol file: 109276-34-8.mol

Synonyms:6-BACH;biotin-6-aminocaproyl hydrazide

Chemical Property of Biotinamidocaproyl hydrazide

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 4.43E-24mmHg at 25°C
• Melting Point: 195-196oC
• Boiling Point: 777 °C at 760 mmHg
• PKA: 13.26±0.35(Predicted)
• Flash Point: 423.7 °C
• PSA: 150.65000
• Density: 1.188 g/cm³
• LogP: 2.51840
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 25 mg/mL
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 371.19911098
• Heavy Atom Count: 25
• Complexity: 477

Purity/Quality:

98%,99%, ^*data from raw suppliers

N''-Biotinyl-6-aminohexanoylhydrazide >97.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)NCCCCCC(=O)NN)NC(=O)N2
• Isomeric SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCCCC(=O)NN)NC(=O)N2
• 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.
• 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.

Technology Process of Biotinamidocaproyl hydrazide

There total 4 articles about Biotinamidocaproyl hydrazide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl 6-(+)-biotinylamidohexanoate → (5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(6-hydrazinyl-6-oxohexyl)pentanamide) (109276-34-8)

Guidance literature:

With hydrazine hydrate; In methanol; for 17h;

DOI:10.1016/j.bmcl.2019.01.015

Reference yield:

N-(+)-biotinyl-6-aminocaproic acid (72040-64-3) → (5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(6-hydrazinyl-6-oxohexyl)pentanamide) (109276-34-8)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 20 °C

2: hydrazine hydrate / methanol / 17 h

With thionyl chloride; hydrazine hydrate; In methanol;

DOI:10.1016/j.bmcl.2019.01.015

Reference yield:

biotin (58-85-5,22879-79-4) → (5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(6-hydrazinyl-6-oxohexyl)pentanamide) (109276-34-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C

2: sodium hydrogencarbonate / water; acetone / 12 h / 20 °C

3: thionyl chloride / 20 °C

4: hydrazine hydrate / methanol / 17 h

With 1-hydroxy-pyrrolidine-2,5-dione; thionyl chloride; hydrazine hydrate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmcl.2019.01.015

upstream raw materials:

N-(+)-biotinyl-6-aminocaproic acid

biotin

biotin N-Hydroxysuccinimide ester

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