D-Arginine

Base Information

• Chemical Name: D-Arginine
• CAS No.: 157-06-2
• Deprecated CAS: 134309-35-6
• Molecular Formula: C6H14N4O2
• Molecular Weight: 174.203
• Hs Code.: 29252000
• European Community (EC) Number: 205-866-5
• UNII: R54Z304Z7C
• DSSTox Substance ID: DTXSID40883354
• Nikkaji Number: J9.186C
• Wikidata: Q27076987
• NCI Thesaurus Code: C77308
• Metabolomics Workbench ID: 38323
• ChEMBL ID: CHEMBL212301
• Mol file: 157-06-2.mol

Synonyms:D-Arginine;157-06-2;(R)-2-amino-5-guanidinopentanoic acid;H-D-Arg-OH;D-(-)-Arginine;D-Arginin;Arginine, d-;D-Arg;D-2-Amino-5-guanidinovaleric acid;(-)-D-Arginine hydrate;EINECS 205-866-5;(2R)-2-amino-5-(diaminomethylideneamino)pentanoic acid;UNII-R54Z304Z7C;(2R)-2-amino-5-carbamimidamidopentanoic acid;CHEBI:15816;R54Z304Z7C;(2R)-2-amino-5-guanidinopentanoic acid;(2R)-2-amino-5-(carbamimidamido)pentanoic acid;C6H14N4O2;(2R)-2-amino-5-[(diaminomethylidene)amino]pentanoic acid;MFCD00063116;H-D-Arginine;61155-84-8;1-deamino-d-arginine;D-Arginine, free base;ST069338;D09FOD;SCHEMBL29456;D-2-Amino-5-guanidinovalerate;CHEMBL212301;GTPL4680;D-Arginine, >=98% (TLC);DTXSID40883354;(R)-2-amino-5-guanidinopentanoicacid;AKOS015854119;AKOS032949749;AM81499;CS-W017497;DB04027;DS-2689;HY-W016781;NCGC00142610-01;NCGC00142610-02;AC-24126;BP-13299;LS-21577;(R,S)-2-Amino-5-guanidino-pentanoic acid;A1029;A-8500;C00792;EN300-136668;M02984;J-300021;7ED4AEC1-F8D9-4AC0-9634-54CEEF53DF5E;Q27076987;Z1201618596

Chemical Property of D-Arginine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 226 °C (dec.)(lit.)
• Refractive Index: -23 ° (C=8, 6mol/L HCl)
• Boiling Point: 409.1 °C at 760 mmHg
• PKA: 2.49±0.24(Predicted)
• Flash Point: 201.2 °C
• PSA: 125.22000
• Density: 1.46 g/cm³
• LogP: 0.55280
• Storage Temp.: Store at 0-5
• Sensitive.: Air Sensitive
• Solubility.: Aqueous Acid (Slightly), Water (Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: -4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 174.11167570
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

99% ^*data from raw suppliers

D-Arginine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36-36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(C(=O)O)N)CN=C(N)N
• Isomeric SMILES: C(C[C@H](C(=O)O)N)CN=C(N)N
• Description: D-arginine is the D-form of arginine, which is a kind of amino acids. It can be reacted with hydrogen peroxide for non-enzymatic synthesis of nitric oxide. It has certain pharmacological activities. For example, its derivative, 1-deamino-8-D-arginine vasopressin is useful for the management of haemophilia and von Willebrand’s disease. It also has the potential to inhibit the proliferation of certain cancer cells. In biological research, D-arginine is frequently used in the studies of L-arginine/nitric oxide pathway as an inactive form of L-arginine.
• Uses: Arginine is an essential amino acid found in food and plant sources, and many biological systems. D-Arginine is extensively used in studies on L-arginine/nitric oxide pathway as an inactive form of L-arginine, even in man. D-Arginine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). D-Arginine can be found in human epidermis and platelet tissues. Within the cell, D-arginine is primarily located in the peroxisome. D-Arginine specifically can inhibit arginine decarboxylase enzymes and also functions as a metabolite. 1-Deamino-8-D-arginine vasopressin makes a new pharmacological approach to the management of haemophilia and von Willebrand's disease. A novel nonenzymatic pathway for the generation of nitric oxide is by the reaction of hydrogen peroxide and d- or l-arginine.

Technology Process of D-Arginine

There total 25 articles about D-Arginine 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:

2-Benzyloxycarbonylamino-5-guanidino-pentanoic acid (1234-35-1,5619-02-3,6382-93-0) → L-arginine (74-79-3,157-06-2,7004-12-8,7200-25-1,25212-18-4) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With N^α-benzyloxycarbonyl amino acid urethane hydrolase II; cobalt(II); at 33 ℃; for 0.5h; Rate constant; pH=6.5;

Reference yield:

callipeltin N → D-Alanine (338-69-2,25191-17-7,18875-37-1) + D-Threonine (632-20-2,134357-96-3,7013-32-3,82822-12-6) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + D-arginine (157-06-2,25212-18-4) + pipecolinic acid (3105-95-1,83680-83-5)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 24h;

DOI:10.1016/j.tet.2016.09.016

Reference yield:

callipeltin O → D-Alanine (338-69-2,25191-17-7,18875-37-1) + D-Threonine (632-20-2,134357-96-3,7013-32-3,82822-12-6) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + D-arginine (157-06-2,25212-18-4) + pipecolinic acid (3105-95-1,83680-83-5)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 24h;

DOI:10.1016/j.tet.2016.09.016

upstream raw materials:

(2R)-2-acetamido-5-guanidino-pentanoate

Arg

D-3-bromocamphor-10-sulfonic acid ammonium salt

Downstream raw materials:

D-Allooectopin

N^α-((S)-1-carboxy-ethyl)-D-arginine

methyl (2R)-2-amino-5-carbamimidamidopentanoate dihydrochloride

Z(OMe)-Tyr-D-Arg-OH HCl

Refernces

• 1、 Garcia, Angel,Vazquez, Maria Jesus,Quinoa, Emilio,Riguera, Ricardo,Debitus, Cecile. "New amino acid derivatives from the marine ascidian Leptoclinides dubius". . p. 782 - 785. Retrieved 1996.
• 2、 Wu, Peng,Wu, Yuping,Zhang, Junhui,Lu, Zhenyu,Zhang, Mei,Chen, Xuexian,Yuan, Liming. "Chromatographic Resolution of α-Amino Acids by (R)-(3,3'-Halogen Substituted-1,1'-binaphthyl)-20-crown-6 Stationary Phase in HPLC". supporting information. p. 1037 - 1042. Retrieved 2017/07/25.
• 3、 Stierhof, Marc,Hansen, Kine ?stnes,Sharma, Mukesh,Feussner, Klaus,Subko, Karolina,Díaz-Rullo, Fernando Fernández,Isaksson, Johan,Pérez-Victoria, Ignacio,Clarke, David,Hansen, Espen,Jaspars, Marcel,Tabudravu, Jioji N.. "New cytotoxic callipeltins from the Solomon Island marine sponge Asteropus sp.". . p. 6929 - 6934. Retrieved 2016/10/14.