BOC-BIOCYTIN

Base Information

• Chemical Name: BOC-BIOCYTIN
• CAS No.: 62062-43-5
• Molecular Formula: C21H36N4O6S
• Molecular Weight: 472.606
• DSSTox Substance ID: DTXSID50583398
• Nikkaji Number: J1.782.884C
• Mol file: 62062-43-5.mol

Synonyms:L-Lysine,N2-[(1,1-dimethylethoxy)carbonyl]-N6-[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-1-oxopentyl]-,[3aS-(3aa,4b,6aa)]-;1H-Thieno[3,4-d]imidazole, L-lysine deriv.;

Chemical Property of BOC-BIOCYTIN

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 4.53E-28mmHg at 25°C
• Melting Point: 132
• Refractive Index: 1.526
• Boiling Point: 799.5 °C at 760 mmHg
• Flash Point: 437.4 °C
• PSA: 171.16000
• Density: 1.202 g/cm³
• LogP: 3.41600
• Storage Temp.: -15°C
• Solubility.: DMSO, Methanol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 14
• Exact Mass: 472.23555605
• Heavy Atom Count: 32
• Complexity: 684

Purity/Quality:

98%Min ^*data from raw suppliers

N-t-Boc-biocytin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCCCNC(=O)CCCCC1C2C(CS1)NC(=O)N2)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2)C(=O)O
• Description: N-Boc-Biocytin is a biotin PEG linker containing a carboxylic group and Boc-protected amine. Reaction of carboxylic with primary amino (-NH2) forms stable, irreversible amide bonds. The Boc group can be deprotected under acidic condition to obtain the free amine which can be used for further conjugations.
• Uses: An intermediate in the synthesis of biocytin-containing peptides

Technology Process of BOC-BIOCYTIN

There total 6 articles about BOC-BIOCYTIN 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: 83.0%

C22H38N4O6S (756450-07-4) → Boc-Lys(biotinyl)-OH (62062-43-5)

Guidance literature:

With sodium hydroxide; In methanol; water; at 0 - 20 ℃; for 5.5h;

DOI:10.1021/ja209641t

Reference yield: 76.0%

Boc-Lys-OH (13734-28-6) + biotin N-Hydroxysuccinimide ester (35013-72-0) → Boc-Lys(biotinyl)-OH (62062-43-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; for 20h; Ambient temperature;

DOI:10.1006/bioo.1995.1013

Reference yield:

5-((3aS)-2-oxo-1-trifluoroacetyl-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid 4-nitro-phenyl ester (62062-42-4) → Boc-Lys(biotinyl)-OH (62062-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. EtOH / Heating

2: Py, aq. NaOH

With pyridine; sodium hydroxide; ethanol;

DOI:10.1021/ja00443a040

upstream raw materials:

Boc-Lys-OH

D-(+)-biotin 2-nitrophenyl ester

biotin N-Hydroxysuccinimide ester

5-((3aS)-2-oxo-1-trifluoroacetyl-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid 4-nitro-phenyl ester

Downstream raw materials:

C₇₀H₁₀₀N₈O₁₉S₂

NHS-N-t-Boc-biocytin

(S)-2-{(S)-2-tert-Butoxycarbonylamino-6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-3-(4-hydroxy-phenyl)-propionic acid

3-[N⁶-biotinyl-N²-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol

Refernces

• 1、 Finn, Frances M.,Yamanouchi, Keitaro,Titus, Gail,Hofmann, Klaus. "Trifunctional Reagents for Derivatizing Sulfhydryl Groups". . p. 152 - 168. Retrieved 2007/10/02.