Fmoc-Lys(Dabcyl)-OH

Base Information

• Chemical Name: Fmoc-Lys(Dabcyl)-OH
• CAS No.: 146998-27-8
• Molecular Formula: C₃₆H₃₇N₅O₅
• Molecular Weight: 619.72
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID60373222
• Nikkaji Number: J1.365.535I
• Mol file: 146998-27-8.mol

Synonyms:Fmoc-Lys(Dabcyl)-OH;146998-27-8;(2S)-6-[[4-[[4-(dimethylamino)phenyl]diazenyl]benzoyl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid;(S,E)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(4-((4-(dimethylamino)phenyl)diazenyl)benzamido)hexanoic acid;1217444-54-6;Fmoc-L-Lys(Dabcyl)-OH;MFCD00467694;Nalpha-Fmoc-Nepsilon-Dabcyl-L-lysine;starbld0019676;DTXSID60373222;AKOS025289437;AKOS030241545;HY-W048204;CS-0100601;F12337;Na-fmoc-ne-dimethylaminophenyldiazobenzoyl-L-lysine;N -4-[4-(Dimethylamino)phenylazo)benzoyl]-Nalpha-Fmoc-L-lysine;Nalpha-Fmoc-Nepsilon-Dabcyl-L-lysine, technical, >=90% (HPLC);(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(4-((4-(dimethylamino)phenyl)diazenyl)benzamido)hexanoic acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-epsilon-4-[4'-(dimethylamino)phenylazo]-benzoyl-L-lysine

Chemical Property of Fmoc-Lys(Dabcyl)-OH

Chemical Property:

• PSA: 136.18000
• Density: 1.26
• LogP: 7.65530
• Storage Temp.: 2-8°C
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 14
• Exact Mass: 619.27946930
• Heavy Atom Count: 46
• Complexity: 1000

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)N=NC2=CC=C(C=C2)C(=O)NCCCCC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Isomeric SMILES: CN(C)C1=CC=C(C=C1)N=NC2=CC=C(C=C2)C(=O)NCCCC[C@@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
• Uses: Fmoc-Lys(Dabcyl)-OH is a building block for in-sequence Lys labeling.

Technology Process of Fmoc-Lys(Dabcyl)-OH

There total 2 articles about Fmoc-Lys(Dabcyl)-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: 72.0%

4-((4-(dimethylamino)phenyl)azo)benzoic acid succinimidyl ester (146998-31-4,1155356-49-2) + 9-fluorenylmethoxycarbonyl-L-alanine hydrochloride (139262-23-0) → N-α-Fmoc-N-ε-(4,4-dimethylaminoazobenzene-4′carbonyl)-L-lysine (146998-27-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield: 40.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Nα-dabcyllysine (185503-99-5) → Nε-dabcyl-Nα-(9-fluorenylmethoxy)carbonyllysine (146998-27-8)

Guidance literature:

With sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; acetonitrile; at 20 ℃;

DOI:10.1080/00397910008087416

Reference yield:

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-[2-[(5-sulfo-1-naphthyl)amino]ethylamino]pentanoic acid (193475-66-0) + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + N-α-Fmoc-N-ε-(4,4-dimethylaminoazobenzene-4′carbonyl)-L-lysine (146998-27-8) + C25H22NO5Pol + N-Fmoc L-Phe (35661-40-6) + Fmoc-Thr-OH (73731-37-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → C72H97N17O19S2

Guidance literature:

C₂₅H₂₂NO₅Pol; With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 0.666667h; Wang resin

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-[2-[(5-sulfo-1-naphthyl)amino]ethylamino]pentanoic acid; With N-[({[(1E)-1-cyano-2-ethoxy-2-oxoethylidene]amino}oxy)(morpholin-4-yl)methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60 ℃; for 1h; Wang resin

N-(fluoren-9-ylmethoxycarbonyl)glycine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-α-Fmoc-N-ε-(4,4-dimethylaminoazobenzene-4′carbonyl)-L-lysine; N-Fmoc L-Phe; Fmoc-Thr-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; Further stages;

DOI:10.1021/acscombsci.7b00193

upstream raw materials:

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

N^α-dabcyllysine

4-((4-(dimethylamino)phenyl)azo)benzoic acid succinimidyl ester

9-fluorenylmethoxycarbonyl-L-alanine hydrochloride

Refernces

• 1、 Shen, Zongxuan,Zhang, Yawen,Chen, Yan. "Synthesis of dye-labeled lysine derivatives". . p. 2525 - 2532. Retrieved 2007/10/03.