FMOC-LYS(BIOTIN)-OH

Base Information

• Chemical Name: FMOC-LYS(BIOTIN)-OH
• CAS No.: 146987-10-2
• Molecular Formula: C31H38N4O6S
• Molecular Weight: 594.732
• Hs Code.: 2934 99 90
• DSSTox Substance ID: DTXSID50452858
• Nikkaji Number: J623.701K
• Wikidata: Q72478105
• Mol file: 146987-10-2.mol

Synonyms:L-Lysine,N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-N6-[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl)-1-oxopentyl]-,[3aS-(3aa,4b,6aa)]-;Fmoc-lys(biotin)-OH;Fmoc-n-epsilon-biotinyl-l-lysine;

Chemical Property of FMOC-LYS(BIOTIN)-OH

Chemical Property:

• Melting Point: 178-180 °C(Solv: methanol (67-56-1); N,N-dimethylformamide (68-12-2))
• Boiling Point: 936.166 °C at 760 mmHg
• PKA: 3.88±0.21(Predicted)
• Flash Point: 519.974 °C
• PSA: 171.16000
• Density: 1.272 g/cm³
• LogP: 5.43000
• Storage Temp.: -15°C
• Solubility.: DMSO (Slightly, Heated)
• Water Solubility.: Slightly soluble in water and dimethyl sulfoxide.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 15
• Exact Mass: 594.25120612
• Heavy Atom Count: 42
• Complexity: 946

Purity/Quality:

99% ^*data from raw suppliers

Nα-Fmoc-Nε-biotinyl-L-lysine ^*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)NCCCCC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)NC(=O)N2
• Isomeric SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)NC(=O)N2
• Uses: Nα-Fmoc-Nε-biotinyl-L-lysine is useful in the synthesis of site-specific biotinylated probes.

Technology Process of FMOC-LYS(BIOTIN)-OH

There total 5 articles about FMOC-LYS(BIOTIN)-OH 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: 85.0%

Fmoc-Lys-OH (105047-45-8) + biotin (58-85-5,22879-79-4) → N-α-Fmoc-N-ε-biotinyl-L-lysine (146987-10-2,110990-09-5)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.3184/030823410X12759895186422

Reference yield: 73.0%

Fmoc-Lys-OH (105047-45-8) + biotin N-Hydroxysuccinimide ester (35013-72-0) → N-α-Fmoc-N-ε-biotinyl-L-lysine (146987-10-2,110990-09-5)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.jmedchem.1c01605

Reference yield:

Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → N-α-Fmoc-N-ε-biotinyl-L-lysine (146987-10-2,110990-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 1 h / 20 °C

2: 41.5 g / aq. NaOH / dioxane / 20 °C

With sodium hydroxide; trifluoroacetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1039/b515278j

upstream raw materials:

Fmoc-Lys-OH

biotin N-Hydroxysuccinimide ester

Fmoc-Lys(tert-butoxycarbonyl)

biotin

Downstream raw materials:

biocytin

Refernces

• 1、 Wang, Dongyao,Cao, Yan,Zheng, Leyi,Lv, Diya,Chen, Langdong,Xing, Xinrui,Zhu, Zhenyu,Li, Xiaoyu,Chai, Yifeng. "Identification of Annexin A2 as a target protein for plant alkaloid matrine". supporting information. p. 5020 - 5023. Retrieved 2017/07/11.
• 2、 Feng, Siliang,Li, Senhao,Kang, Xiaoyu,Liu, Keliang. "One step synthesis of biotinylated amino acids". experimental part. p. 348 - 350. Retrieved 2010/10/21.