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H1007

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
NACRES:
NA.26
PubChem Substance ID:
24895420
UNSPSC Code:
12352209
EC Number:
216-045-6
MDL number:
MFCD00012622
Beilstein/REAXYS Number:
4016621

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Product Name

L-Homoarginine hydrochloride, unnatural arginine analog

InChI key

YMKBVNVCKUYUDM-JEDNCBNOSA-N

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

SMILES string

Cl[H].N[C@@H](CCCCNC(N)=N)C(O)=O

assay

≥98% (TLC)

form

powder

color

white to off-white

mp

213-215 °C (lit.)

solubility

H2O: soluble

application(s)

peptide synthesis

Quality Level

200

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This Item
A5131H6503H6647
L-Homoarginine hydrochloride unnatural arginine analog

Sigma-Aldrich

H1007

L-Homoarginine hydrochloride

L-Arginine monohydrochloride reagent grade, ≥98% (HPLC), powder

Sigma-Aldrich

A5131

L-Arginine monohydrochloride

L-Homocysteine thiolactone hydrochloride ≥98% (TLC)

Sigma-Aldrich

H6503

L-Homocysteine thiolactone hydrochloride

L-Histidinol dihydrochloride ≥98 (TLC)

Sigma-Aldrich

H6647

L-Histidinol dihydrochloride

form

powder

form

powder

form

powder

form

powder

assay

≥98% (TLC)

assay

≥98% (HPLC)

assay

≥98% (TLC)

assay

≥98% (TLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

color

white to off-white

color

white

color

white

color

white to off-white

mp

213-215 °C (lit.)

mp

>235 °C

mp

185 °C

mp

198-201 °C (dec.) (lit.)

solubility

H2O: soluble

solubility

H2O: 50 mg/mL

solubility

-

solubility

-

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF1042V
MKCQ9509
WXBD8621V
MKCR8187
MKCP3931

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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
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
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-/-
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
View All Related Papers

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