L-Homoarginine

Base Information

• Chemical Name: L-Homoarginine
• CAS No.: 156-86-5
• Deprecated CAS: 13094-78-5
• Molecular Formula: C7H16N4O2
• Molecular Weight: 188.23
• Hs Code.: 29152900
• UNII: JF751CK38I
• DSSTox Substance ID: DTXSID70926980
• Nikkaji Number: J24H
• Wikipedia: Homoarginine
• Wikidata: Q57828472
• Metabolomics Workbench ID: 37359
• ChEMBL ID: CHEMBL589752
• Mol file: 156-86-5.mol

Synonyms:Homoarginine

Chemical Property of L-Homoarginine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.06E-06mmHg at 25°C
• Melting Point: 207-209 °C
• Refractive Index: 1.586
• Boiling Point: 414.1 °C at 760 mmHg
• PKA: 2.52±0.24(Predicted)
• Flash Point: 202.4 °C
• PSA: 125.22000
• Density: 1.39 g/cm³
• LogP: 0.94290
• Storage Temp.: Store at RT.
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 188.12732577
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

98%min ^*data from raw suppliers

Homoarginine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,Xi
• Hazard Codes: Xn,N,Xi

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C(CCN=C(N)N)CC(C(=O)O)N
• Isomeric SMILES: C(CCN=C(N)N)C[C@@H](C(=O)O)N
• Recent ClinicalTrials: Homoarginine Supplementation in Patients After Stroke
• Description: Homoarginine and 1-hydroxyhomoarginine were originally detected in significant concentration in the seeds of many Lathyrus species (Bell, 1962a,b; 1963). Homoarginine was isolated from the seeds of L. cicera (Bell, 1962b) and L. sativus (Rao et al., 1963). The hydroxy compound was obtained from the seeds of L. tingitanus (Bell, 1964). The comparative distribution of guanidino compounds in the seeds of two genus of the Papilionoideae, Lathyrus and Vicia, exhibits interesting features (Bell and Tirimanna, 1964). For example, the genus Lathyrus stores predominantly the C7 amino acids homoarginine, y-hydroxyhomoarginine and the related compound lathyrine, while the genus Vicia stores relatively high concentrations of canavanine and of the C6 amino acids arginine and y-hydroxyarginine. Apart from plants, homoarginine was found in small amounts in human body fluids ,. urine (Armstrong, 1967), serum (Matsumoto et al., 1976a) and cerebrospinal fluid (Mori et al., 1981b) and in mammalian brain (Mori et al., 1978, 1979 ). Increased urinary excretion was reported in hyperlysinemia (Armstrong and Robinow, 1967) and citrullinemia (Scott-Emuakpor et al., 19(2). Homoarginine may be formed in mammals from lysine, by a homologous urea cycle in which arginine is replaced by lysine (Ryan and Wells, 1964; Scott-Emuakpor et al., 19(2). The excretion of homocitrulline and homoarginine in urine following administration of lysine to children supports this theory (Buergi et al., 1966). The biosynthesis of homoarginine has not been examined in plants, but y-hydroxyhomoarginine is synthesized from homoarginine in Lathyrus seeds (Bell, 1964). Subsequently both compounds have been identified as the precursors of the cyclic guanidino derivative, lathyrine, also present in Lathyrus seeds (Bell and Przybylska, 1965). Homoarginine and y-hydroxyhomoarginine probably serve as nitrogen reserves in Lathyrus seeds. Inhibition of growth by homoarginine has been reported In various microorganisms (Walker, 1955; Rao et al., 1963). gama-Hydroxyhomoarginine lactone isolated from the seeds of L. tingitanus (Bell, 1964) probably results from the cyclization of the open chain compound under acidic conditions.
• Uses: Homoarginine is an inhibitor of human arginase activity. Homoarginine as marker for exogenous protein Absorption and secretion of free homoarginine in the intestine: when 9 mmol homoarginine were infused into the proximal part of the jejunum, there was a 99.9% disappearance of the free amino acid homoarginine up to the ileum. In addition, following the infusion of 9 mmol homoarginine into the vena jugularis less than 0.2% of the infused homoarginine appeared in the intestine. We concluded from these data that with the homoarginine method endogenous protein in the chyme of the intestine can be distinguished from the food protein as homoarginine is not incorporated into endogenous secreta and free homo arginine is completely absorbed.

Technology Process of L-Homoarginine

There total 13 articles about L-Homoarginine 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:

lucentamycin E (1395754-40-1) → L-homoarginine (156-86-5) + (2S,3R,E)-3-methyl-4-ethylideneproline + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 2h;

DOI:10.1021/np3003854 DOI:10.1021/np3003854

Reference yield:

→ homoarginine (156-86-5)

Guidance literature:

With phosphonium iodide; hydrogen iodide; at 85 ℃; N⁶-carbamimidoyl-DL-lysine;

Reference yield:

→ homoarginine (156-86-5)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo01228a008

upstream raw materials:

2,6-diaminocaproic acid

CYANAMID

2-ethylisothiourea hydrobromide

bromocyane

Downstream raw materials:

N²-benzoyl-N⁶-carbamimidoyl-DL-lysine

H-Har(HCl)-OMe*2HCl

Boc-Tyr(Et)-Har-OMe

Z-Tyr(tert-Bu)-Har-OMe

Refernces

• 1、 Cha, Jin Wook,Park, Jin-Soo,Sim, Taebo,Nam, Sang-Jip,Kwon, Hak Cheol,Del Valle, Juan R.,Fenical, William. "Structure assignment of lucentamycin e and revision of the olefin geometries of the marine-derived lucentamycins". . p. 1648 - 1651. Retrieved 2013/01/15.
• 2、 Pundak, Shlomo,Wilchek, Meir. "Synthesis of Guanidino-N-alkylarginines by the Use of Polymeric Pseudoureas". . p. 808 - 809. Retrieved 2007/10/02.