ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Arginine derivatives L(+)-Homoarginine hydrochloride

L(+)-Homoarginine hydrochloride

Product NameL(+)-Homoarginine hydrochloride
CAS1483-01-8
MFC7H17ClN4O2
MW224.69
EINECS216-045-6
MOL File1483-01-8.mol

Chemical Properties

Melting point	213-215 °C(lit.)
alpha	18 º (c=1, 1N HCl)
storage temp.	Inert atmosphere,Room Temperature
solubility	H₂O: 50 mg/mL, clear to slightly hazy, faintly yellow
form	Granular Powder
color	White
Water Solubility	Soluble in water(50 mg/mL).
BRN	4016621
Stability	Moisture Sensitive
InChI	InChI=1/C7H16N4O2.ClH/c8-5(6(12)13)3-1-2-4-11-7(9)10;/h5H,1-4,8H2,(H,12,13)(H4,9,10,11);1H/t5-;/s3
InChIKey	YMKBVNVCKUYUDM-USHJBNIQNA-N
SMILES	C(CCCNC(=N)N)[C@H](N)C(=O)O.Cl \|&1:8,r\|
CAS DataBase Reference	1483-01-8(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	24/25-36/37/39-27-26
WGK Germany	3
HS Code	29252900

MSDS

Provider	Language
L(+)-Homoarginine hydrochloride	English
SigmaAldrich	English
ACROS	English

Usage And Synthesis

Description

L-Homoarginine is an uncompetitive and organ-specific inhibitor of alkaline phosphatases. This non-essential amino acid inhibits human bone and liver alkaline phosphatases but has no effect on placental or intestinal isoenzymes. In vitro, L-homoarginine inhibits [³H]thymidine uptake by mouse myeloma MOPC 104E cells and inhibits proliferation of C3H/He mouse osteosarcoma cells. Pre-treatment with L-homoarginine delays in vivo tumor growth in a murine C3H/He osteosarcoma model. It also inhibits high-protein diet-induced pancreatic growth and enzyme secretion in bile-pancreatic juice-diverted rats, a model for the induction of pancreatic enzyme secretion with hypercholecystokininemia.

Chemical Properties

White Powder

Uses

An inhibitor of alkaline phosphatase isoenzymes. It is also an inhibitor of cellular transport of arginine by a sodium-independent high affinity y+ transporter. The substitution of homoarginine for arginine or lysine renders proteins resistant to proteolysis by trypsin. Arginine residues are often located at the active centers of proteins and enzymes. Replacing these arginines with homoarginine can elucidate protein function and structural requirements.

Uses

An inhibitor of alkaline phosphatase isoenzymes. An analog of Homoarginine (H585000).

Biochem/physiol Actions

Homoarginine is an inhibitor of tissue nonspecific alkaline phosphatase (TNALP). It is also an inhibitor of cellular transport of arginine by a sodium-independent high affinity y+ transporter.

IC 50

Human Endogenous Metabolite

References

[1] CHI-WEI LIN W F. L-Homoarginine. An organ-specific, uncompetitive inhibitor of human liver and bone alkaline phosphohydrolases.[J]. The Journal of Biological Chemistry, 1972, 16 1: 3082-3087. DOI: 10.1016/s0021-9258(19)45215-0
[2] Y KIKUCHI K K I Kizawa. [Inhibitory effect of L-homoarginine on murine osteosarcoma cell proliferation].[J]. Japanese Journal of Cancer and Chemotherapy, 1982, 9 5: 888-897.
[3] T. HIRA H. H S Ohyama. l-Homoarginine suppresses exocrine pancreas in rats[J]. Amino Acids, 2003, 24 4: 389-396. DOI: 10.1007/s00726-002-0344-2

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