All Photos(1)
Synonym(s):
(S)-2-Amino-6-guanidinohexanoic acid hydrochloride
Linear Formula:
H2NC(=NH)NH(CH2)4CH(NH2)CO2H · HCl
CAS Number:
Molecular Weight:
224.69
Beilstein:
4016621
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26
Recommended Products
Quality Level
Assay
≥98% (TLC)
form
powder
color
white to off-white
mp
213-215 °C (lit.)
solubility
H2O: soluble
application(s)
peptide synthesis
SMILES string
Cl[H].N[C@@H](CCCCNC(N)=N)C(O)=O
InChI
1S/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-;/m0./s1
InChI key
YMKBVNVCKUYUDM-JEDNCBNOSA-N
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Related Categories
Application
L-Homoarginine may be used to create non-natural proteins for studies of post-translational protein modifications. 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. L-Homoarginine is used to study the mechanisms of nitric oxide production by cells via nitric oxide synthase(s). L-Homoarginine is used as a selective mammalian alkaline phosphatase isoenzyme inhibitor. The substitution of homoarginine for arginine or lysine renders proteins resistant to proteolysis by trypsin.
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.
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.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Szilvia Erdélyi-Bótor et al.
Cephalalgia : an international journal of headache, 37(6), 571-580 (2016-05-22)
Background/Aim Migraine is a risk factor for the formation of silent brain white matter lesions (WMLs) that are possibly ischemic in nature. Although dysfunction of the L-arginine/nitric oxide (NO) pathway has been associated with oxidative stress and endothelial dysfunction in
Amino acids as modulators of endothelium-derived nitric oxide.
Kakoki M, Kim HS, Edgell CJ, et al.
American Journal of Physiology: Renal Physiology, 291, F297-F304 (2006)
Azin Nowrouzi et al.
Biochemical and biophysical research communications, 330(2), 400-409 (2005-03-31)
Liver tissue is the source of 90% of serum alkaline phosphatase (AP). The serum levels and structures of tumor marker proteins change under many disease conditions as well as cancer. The study was aimed at determining the type of alkaline
J Fernandes et al.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas, 41(1), 41-46 (2007-12-22)
Our objective was to characterize the modulation of the activity of Saccharomyces cerevisiae alkaline phosphatases (ALPs) by classic inhibitors of ALP activity, cholesterol and steroid hormones, in order to identify catalytic similarities between yeast and mammalian ALPs. S. cerevisiae expresses
Michael D Wetzel et al.
Physiological reports, 9(5), e14766-e14766 (2021-03-14)
Recently we showed that homoarginine supplementation confers kidney protection in diabetic mouse models. In this study we tested whether the protective effect of homoarginine is nitric oxide synthase-3 (NOS3)-independent in diabetic nephropathy (DN). Experiments were conducted in NOS3 deficient (NOS3-/-
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