Fmoc-Lys(Fmoc)-OH

Base Information

• Chemical Name: Fmoc-Lys(Fmoc)-OH
• CAS No.: 78081-87-5
• Molecular Formula: C₃₆H₃₄N₂O₆
• Molecular Weight: 590.676
• Hs Code.: 2924 29 70
• European Community (EC) Number: 812-209-1
• ChEMBL ID: CHEMBL4634184
• DSSTox Substance ID: DTXSID30549391
• Nikkaji Number: J1.553.425G
• Wikidata: Q72445829
• Mol file: 78081-87-5.mol

Synonyms:Fmoc-Lys(Fmoc)-OH;78081-87-5;(2S)-2,6-bis(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid;N,N'-Bis-Fmoc-L-lysine;MFCD00080275;FmocLys(Fmoc)OH;SCHEMBL178733;CHEMBL4634184;DTXSID30549391;Nalpha,Nepsilon-di-Fmoc-L-lysine;AKOS015907339;AKOS015922842;CS-W008386;HY-W008386;DS-15337;B4931;Fmoc-Lys(Fmoc)-OH, >=98.0% (HPLC);N,N'-bis-(9-fluorenylmethoxycarbonyl)lysine;F11045;EN300-6488264;J-300178;Q-101581;Nalpha,Nepsilon-di-(9-fluorenylmethoxycarbonyl)-L-lysine;N2,N6-Bis(((9H-fluoren-9-yl)methoxy)carbonyl)-L-lysine;N~2~,N~6~-Bis{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-lysine;Nalpha,Nepsilon-Bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysine;(S)-2,6-bis(((9H-fluoren-9-yl)methoxy)carbonylamino)hexanoic acid;(2S)-2,6-bis({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid;N-alpha-N-epsilon-Bis(9-fluorenylmethyloxycarbonyl)-L-lysine (Fmoc-L-Lys(Fmoc)-OH)

Chemical Property of Fmoc-Lys(Fmoc)-OH

Chemical Property:

• Vapor Pressure: 1.36E-29mmHg at 25°C
• Melting Point: 120-130 °C
• Refractive Index: 1.629
• Boiling Point: 835.2 °C at 760 mmHg
• PKA: 3.88±0.21(Predicted)
• Flash Point: 458.9 °C
• PSA: 113.96000
• Density: 1.278 g/cm³
• LogP: 7.46910
• Storage Temp.: 2-8°C
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 590.24168681
• Heavy Atom Count: 44
• Complexity: 946

Purity/Quality:

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

Fmoc-Lys(Fmoc)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCCCC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCCC[C@@H](C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Uses: Fmoc-Lys(Fmoc)-OH is useful derivative for the synthesis of branched peptides. Fmoc-Lys(Fmoc)-OH is used in the synthesis of [Lys8]-oxytocin related dendrimer which were functionally active in vitro on human oxytocin receptors and inhibited colonic nociceptors potently in a mouse model of chronic abdominal pain.

Technology Process of Fmoc-Lys(Fmoc)-OH

There total 5 articles about Fmoc-Lys(Fmoc)-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: 93.0%

L-Lysine hydrochloride (657-27-2,10098-89-2,26124-78-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-2,N-6-bis(9-fluorenylmethyloxycarbonyl)-L-lysine (75932-02-4,78081-87-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 3h; pH=8.5;

DOI:10.1134/S1068162007010153

Reference yield: 71.0%

L-lysine (56-87-1,3506-25-0) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → N-2,N-6-bis(9-fluorenylmethyloxycarbonyl)-L-lysine (75932-02-4,78081-87-5)

Guidance literature:

Reference yield: 46.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → N-2,N-6-bis(9-fluorenylmethyloxycarbonyl)-L-lysine (75932-02-4,78081-87-5)

Guidance literature:

Fmoc-Lys(tert-butoxycarbonyl); With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

(fluorenylmethoxy)carbonyl chloride; With sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.9b02119

upstream raw materials:

L-lysine

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-Lysine hydrochloride

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

(S)-2,6-Diamino-hexanoic acid {2-[2-(2,4-dichloro-phenoxy)-acetylamino]-ethyl}-amide

C₇₀H₁₀₅N₁₆O₂₀PS₂

C₈₅H₁₂₇N₂₀O₂₂PS₂

C₉₆H₁₄₄N₃₀O₁₇

Refernces

• 1、 Tevyashova,Olsufyeva,Preobrazhenskaya,Klyosov,Zomer,Platt. "New conjugates of antitumor antibiotic doxorubicin with water-soluble galactomannan: Synthesis and biological activity". . p. 139 - 145. Retrieved 2008/03/13.
• 2、 -. "Amino acid derivatives as HIV aspartyl protease inhibitors". . . Retrieved 2008/06/13.