Fmoc-L-citrulline

Base Information

• Chemical Name: Fmoc-L-citrulline
• CAS No.: 133174-15-9
• Molecular Formula: C₂₁H₂₃N₃O₅
• Molecular Weight: 397.431
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID10373252
• Wikidata: Q72478214
• Mol file: 133174-15-9.mol

Synonyms:Fmoc-Cit-OH;Fmoc-L-citrulline;133174-15-9;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-ureidopentanoic acid;L-Ornithine, N5-(aminocarbonyl)-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-;Nalpha-Fmoc-L-citrulline;(2S)-5-(carbamoylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid;fmoc-citoh;MFCD00151943;SCHEMBL119468;Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-citrulline;DTXSID10373252;NBMSMZSRTIOFOK-SFHVURJKSA-N;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-ureido-pentanoic acid;AKOS015837234;AKOS015895285;AC-8677;AM82463;CS-W008064;Fmoc-Cit-OH, >=97.0% (HPLC);AS-17492;F0626;EN300-316936;M03232;A806573;J-300338;S-133174-15-9;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-citrulline (Fmoc-L-Cit-OH);(2S)-5-(carbamoylamino)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid

Chemical Property of Fmoc-L-citrulline

Chemical Property:

• Appearance/Colour: White to off white powder
• Vapor Pressure: 6.01E-19mmHg at 25°C
• Melting Point: 168-175ºC
• Refractive Index: -10 ° (C=1, DMF)
• Boiling Point: 671.5oC at 760 mmHg
• PKA: 3.84±0.21(Predicted)
• Flash Point: 359.9oC
• PSA: 130.75000
• Density: 1.316g/cm3
• LogP: 3.90890
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 397.16377084
• Heavy Atom Count: 29
• Complexity: 577

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-Cit-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCNC(=O)N)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CCCNC(=O)N)C(=O)O

Technology Process of Fmoc-L-citrulline

There total 1 articles about Fmoc-L-citrulline 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: 100.0%

Citrulline (372-75-8) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid (133174-15-9)

Guidance literature:

Citrulline; With sodium hydrogencarbonate; In water; at 20 ℃; for 1h;

(fluorenylmethoxy)carbonyl chloride; In 1,2-dimethoxyethane; water;

DOI:10.1016/j.tetlet.2018.08.021

Reference yield: 84.0%

Nα-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine (1097192-04-5,1176270-25-9) + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Pro-OH (71989-31-6) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4) + Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) + Fmoc-L-Gln(Trt)-OH (132327-80-1,200623-62-7) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) + (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid (133174-15-9) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) + Fmoc-L-propargyl-Gly-OH (198561-07-8) → H-Gly-Cys-Pra-Thr-Asp-Pro-Arg-Cys-Cit-Trp-Gln-5-azidoNva-Tyr-OH

Guidance literature:

Fmoc-Tyr(tBu)-OH; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1.5h;

With piperidine; In N,N-dimethyl-formamide; for 0.5h;

N^α-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine; N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-(tBu)Asp-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-Thr(tBu)-OH; Fmoc-L-Gln(Trt)-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Fmoc-L-propargyl-Gly-OH; Further stages;

Reference yield: 77.0%

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid (133174-15-9) + 4-nitrobenzyl chloroformate (4457-32-3) → 14-(9H-fluoren-9-yl)-1-(4-nitrophenyl)-3,5,12-trioxo-2,13-dioxa-4,6,11-triazatetradecane-10-carboxylic acid

Guidance literature:

In tetrahydrofuran; at 40 ℃;

DOI:10.1021/acs.molpharmaceut.8b00741

upstream raw materials:

Citrulline

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

2-(2-{3-[1-(4-bromo-phenyl)-ethyl]-ureido}-5-ureido-pentanoylamino)-3-methyl-butyric acid

symplocamide A

C₃₉H₃₄N₆O₉

C₂₂H₃₃N₅O₆

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