(2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-azaniumylhexanoate

Base Information

• Chemical Name: (2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-azaniumylhexanoate
• CAS No.: 576-19-2
• Molecular Formula: C16H28N4O4S
• Molecular Weight: 372.489
• Hs Code.: 29362900
• Mol file: 576-19-2.mol

Synonyms:

Chemical Property of (2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-azaniumylhexanoate

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.75E-24mmHg at 25°C
• Melting Point: 241-243 °C
• Refractive Index: 1.547
• Boiling Point: 748 °C at 760 mmHg
• PKA: 2.53±0.24(Predicted)
• Flash Point: 406.2 °C
• PSA: 158.85000
• Density: 1.234g/cm³
• LogP: 2.15940
• Storage Temp.: −20°C
• Solubility.: Aqueous Base (Slightly), Water (Slightly, Sonicated)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 372.18312656
• Heavy Atom Count: 25
• Complexity: 485

Purity/Quality:

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

Biocytin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)NCCCCC(C(=O)[O-])[NH3+])NC(=O)N2
• Isomeric SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCC[C@@H](C(=O)[O-])[NH3+])NC(=O)N2
• Description: Biocytin is a conjugate of biotin and lysine known formally as ε-N-(d-biotinyl)-L-lysine. The addition of lysine to biotin increases the chain length extending from biotin, allowing the synthesis of medium-chain reagents. It also provides terminal carboxyl and amino groups for derivatization or conjugation to proteins and other molecules. Covalent linking reactions typically involve carbodiimide or NHS-ester crosslinking chemistries. Biocytin is also used as an anterograde, retrograde, or intracellular neuroanatomical tracer that is fixable with aldehyde-based fixatives. For this and other applications, biocytin is detected with avidin or streptavidin probes.
• Uses: Useful for the synthesis of Biocytin containing peptides to study the mechanism of reactions catalyzed by biotin - containing enzymes Biocytin can be used as a versatile fluorescent marker for neuroanatomical investigations and for a biotinidase assay. Biocytin is used as a substrate to study the specificity and kinetics of biotinidase(s), to measure biotinidase deficiency and as a model compound to study various uptake mechanisms of cells and tissues. Biocytin has been used to label neurons, medium spiny neurons and optic nerves.

Technology Process of (2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-azaniumylhexanoate

There total 17 articles about (2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-azaniumylhexanoate 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: 73.0%

N-(4-((S)-5'-oxo-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-4'-yl)butyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide → biocytin (576-19-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1002/ejoc.201700063

Reference yield:

biotin N-Hydroxysuccinimide ester (35013-72-0) → biocytin (576-19-2)

Guidance literature:

biotin N-Hydroxysuccinimide ester; With sodium hydrogencarbonate; In water; N,N-dimethyl-formamide;

With ethylenediaminetetraacetic acid; In water;

Reference yield:

biotin (58-85-5,22879-79-4) → biocytin (576-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 4-nitro-phenol, Py / 50 °C

2: aq. EtOH / Heating

3: Py, aq. NaOH

4: aq. CF₃CO₂H, anisole

With pyridine; sodium hydroxide; 4-nitro-phenol; ethanol; methoxybenzene; trifluoroacetic acid;

DOI:10.1021/ja00443a040

upstream raw materials:

L-lysine

biotin chloride

N²-formyl-N⁶-[5-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-valeryl]-L-lysine

biotin methyl ester

Downstream raw materials:

2-(4-azido-2,3,5,6-tetrafluorobenzamido)-6-[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanamido]hexanoic acid

N^α-(4-benzoylbenzoyl)-L-biocytin

(S)-2-{2-[2-Nitro-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-acetylamino}-6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid

1-(N-(N^α-(4-benzoylbenzoyl)-L-biocytinoyl)amino)-6-(N'-boc-amino)hexane

Refernces

• 1、 Weijlard et al.. "-". . p. 2505. Retrieved 1954.
• 2、 Wang, Dong-Yao,Cao, Yan,Zheng, Le-Yi,Chen, Lang-Dong,Chen, Xiao-Fei,Hong, Zhan-Ying,Zhu, Zhen-Yu,Li, Xiaoyu,Chai, Yi-Feng. "Target Identification of Kinase Inhibitor Alisertib (MLN8237) by Using DNA-Programmed Affinity Labeling". . p. 10906 - 10914. Retrieved 2017/08/22.