Fmoc-D-Arg-OH

Base Information

• Chemical Name: Fmoc-D-Arg-OH
• CAS No.: 130752-32-8
• Molecular Formula: C₂₁H₂₄N₄O₄
• Molecular Weight: 396.446
• DSSTox Substance ID: DTXSID00427036
• Nikkaji Number: J1.298.082E
• Mol file: 130752-32-8.mol

Synonyms:Fmoc-D-Arg-OH;130752-32-8;FMOC-D-ARGININE;D-Arginine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2R)-5-(diaminomethylideneamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;(2R)-5-(diaminomethylideneazaniumyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoate;N-|A-Fmoc-D-Arginine;N-A-FMOC-D-ARGININE;N-ALPHA-FMOC-D-ARGININE;SCHEMBL18237098;DTXSID00427036;MFCD00077047;AKOS016842936;AC-8581;AM81508;AS-19660;CS-0062084;(R)-2-(Fmoc-amino)-5-guanidinopentanoic acid;EN300-650282;W16692;J-300028;(((9H-FLUOREN-9-YL)METHOXY)CARBONYL)-D-ARGININE;Z1805585500;(2R)-5-carbamimidamido-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid;(R)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-5-GUANIDINOPENTANOIC ACID

Chemical Property of Fmoc-D-Arg-OH

Chemical Property:

• PKA: 3.81±0.21(Predicted)
• PSA: 137.53000
• Density: 1.38 g/cm³
• LogP: 3.82340
• Storage Temp.: -15°C
• 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

Fmoc-D-Arg-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)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-D-arginine is an N-Fmoc-protected form of D-Arginine (A769515). D-Arginine is an unnatural isomer of L-Arginine (A769505), and is used to inhibit glutamate-induced nitric oxide production in rats. Derivatives of D-Arginine are used for pharmaceutical purposes, one example is 1-Deamino-8-D-arginine vasopressin, which is used to treat various bleeding disorders.

Technology Process of Fmoc-D-Arg-OH

There total 15 articles about Fmoc-D-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:

C₃₇H₅₀N₁₀O₁₁

C₃₇H₅₀N₁₀O₁₁

C₆₄H₁₀₇N₁₉O₁₆

neuropeptide FF (Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2)

Refernces

• 1、 Palladino, Pasquale,Stetsenko, Dmitry A.. "New TFA-free cleavage and final deprotection in Fmoc solid-phase peptide synthesis: Dilute HCl in fluoro alcohol". supporting information. p. 6346 - 6349. Retrieved 2013/02/25.
• 2、 Nowshuddin, Shaik,Rao,Reddy, A. Ram. "Efficient procedure for the preparation of oligomer-free N-fmoc amino acids". experimental part. p. 2022 - 2031. Retrieved 2009/11/30.