Fmoc-Arg-OH

Base Information

• Chemical Name: Fmoc-Arg-OH
• CAS No.: 91000-69-0
• Molecular Formula: C21H24N4O4
• Molecular Weight: 396.446
• Hs Code.: 29252900
• European Community (EC) Number: 690-793-5
• DSSTox Substance ID: DTXSID90369198
• Nikkaji Number: J1.298.083C
• Mol file: 91000-69-0.mol

Synonyms:Fmoc-Arg-OH;91000-69-0;FMOC-L-Arginine;FMOC-L-ARG-OH;(2S)-5-(diaminomethylideneamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;N-A-FMOC-L-ARGININE;MFCD00051770;alfa-Fmoc-L-arginine;N-alpha-FMOC-L-ARGININE;Fmoc-Arg;Na-Fmoc-L-arginine;N-|A-Fmoc-L-Arginine;(((9H-fluoren-9-yl)methoxy)carbonyl)-L-arginine;SCHEMBL120403;Fmoc-L-ArginineFmoc-L-Arginine;Fmoc-Arg-OH, >=96.0%;DTXSID90369198;DVBUCBXGDWWXNY-SFHVURJKSA-N;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-guanidino-pentanoic acid;AKOS015837235;AKOS015906885;AM81509;CS-W014466;HY-W013750;AS-14291;Na-(9-Fluorenylmethoxycarbonyl)-L-arginine;EN300-650965;M03403;A843693;J-300029;L-Arginine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-ARGININE;(2S)-5-carbamimidamido-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-5-GUANIDINOPENTANOIC ACID

Chemical Property of Fmoc-Arg-OH

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 145-150 °C(lit.)
• Refractive Index: 1.659
• Boiling Point: 520.14°C (rough estimate)
• PKA: 3.81±0.21(Predicted)
• PSA: 137.53000
• Density: 1.38 g/cm³
• LogP: 3.82340
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Aqueous Acid (Slightly), Chloroform (Slightly), Dimethylformamide (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 396.17975526
• Heavy Atom Count: 29
• Complexity: 586

Purity/Quality:

99% ^*data from raw suppliers

Nα-Fmoc-L-arginine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCN=C(N)N)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CCCN=C(N)N)C(=O)O
• Uses: Nα-Fmoc-L-arginine is an N-Fmoc-protected form of L-Arginine (A769505). L-Arginine is an conditionally essential amino acid for humans and adult mammals as it’s requirements exceed production during certain developmental stages in life (such as pregnancy). L-Arginine also prevents blood toxicity from intravenous amino acid administration in humans.

Technology Process of Fmoc-Arg-OH

There total 14 articles about Fmoc-Arg-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: 56.0%

L-arginine (74-79-3,25212-18-4) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-L-Arg-OH (91000-69-0,130752-32-8)

Guidance literature:

L-arginine; With N-cyclohexyl-cyclohexanamine; In acetone; at 20 ℃;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium carbonate; In water; acetonitrile; at 0 - 20 ℃; pH=8;

With potassium hydrogensulfate; In water; acetonitrile; pH=2 - 3;

DOI:10.1080/00397910802632563

Reference yield:

Nα-Fmoc-Arg(Ng-Pbf)-OH → Fmoc-L-Arg-OH (91000-69-0,130752-32-8)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 0.5h; Concentration; Time; Solvent;

DOI:10.1021/ol303124r

Reference yield:

L-arginine (74-79-3,25212-18-4) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → Fmoc-L-Arg-OH (91000-69-0,130752-32-8)

Guidance literature:

In acetonitrile; at 20 ℃; for 0.25h; pH=9.2; aq. borate buffer;

DOI:10.1002/jccs.201190014

upstream raw materials:

Nα-(9-fluorenylmethoxycarbonyl)-Nγ-(4-methoxy-2,3,6-trimethylbenzenesulphonyl)-L-arginine

N^α-9-Fluorenylmethyloxycarbonyl-N^G-2,4,6-triisopropylbenzenesulphonyl-L-arginine

N^α-9-Fluorenylmethyloxycarbonyl-N^G-4-methoxy-3,5-di-tert-butylbenzenesulphonyl-L-arginine

N^α-9-fluorenylmethyloxycarbonyl-N^G-biphenyl-4-sulphonyl-L-arginine

Downstream raw materials:

Fmoc-Arg-pNA*HCl

bradykinin

Refernces

• 1、 Zhou, Wei,Zhang, Xiao-Yan,Duan, Geng-Li. "Liquid-chromatography quantitative analysis of 20 amino acids after derivatization with FMOC-CI and its application to different origin Radix isatidis". experimental part. p. 509 - 515. Retrieved 2012/01/04.
• 2、 Harris, Paul W.R.,Brimble, Margaret A.. "Synthesis of an arginine tagged [Cys155-Arg180] fragment of NY-ESO-1: elimination of an undesired by-product using 'In house' resins". experimental part. p. 3460 - 3466. Retrieved 2010/04/05.