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H1007

Sigma-Aldrich

L-Homoarginine hydrochloride

≥98% (TLC)

Synonym(s):

(S)-2-Amino-6-guanidinohexanoic acid hydrochloride

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About This Item

Linear Formula:
H2NC(=NH)NH(CH2)4CH(NH2)CO2H · HCl
CAS Number:
1483-01-8
Molecular Weight:
224.69
Beilstein/REAXYS Number:
4016621
EC Number:
216-045-6
MDL number:
MFCD00012622
UNSPSC Code:
12352209
PubChem Substance ID:
24895420
NACRES:
NA.26

product name

L-Homoarginine hydrochloride, unnatural arginine analog

Quality Level

200

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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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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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
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)
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
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-/-
Gabor Tajti et al.
Allergy, asthma, and clinical immunology : official journal of the Canadian Society of Allergy and Clinical Immunology, 14, 2-2 (2018-01-09)
Contribution of nitric-oxide (NO) pathway to the pathogenesis of bronchial asthma (asthma) is ambiguous as NO may confer both protective and detrimental effects depending on the NO synthase (NOS) isoforms, tissue compartments and underlying pathological conditions (e.g. systemic inflammation). Asymmetric
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