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Homoarginine information


Homoarginine

L-Homoarginine
Names
IUPAC name
(2S)-2-Amino-6-(diaminomethylideneamino)hexanoic acid
Other names
  • N6-(Aminoiminomethyl)lysine
  • N6-Amidinolysine
  • 2-Amino-6-guanidinohexanoic acid
Identifiers
CAS Number
  • 156-86-5 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8732
EC Number
  • 216-045-6
PubChem CID
  • 9085
UNII
  • JF751CK38I checkY
InChI
  • InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1
    Key: QUOGESRFPZDMMT-YFKPBYRVSA-N
SMILES
  • C(CCN=C(N)N)C[C@@H](C(=O)O)N
Properties
Chemical formula
C7H16N4O2
Molar mass 188.231 g·mol−1
Appearance White crystalline powder
Density 1.39 g/cm−3
Boiling point 414.1 °C (777.4 °F; 687.2 K) 760 mmHg
Solubility in water
soluble
Vapor pressure 1.06x10–6 mmHg at 25°C
Refractive index (nD)
1.586
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Homoarginine is an nonproteinogenic alpha-amino acid. It is structurally equivalent to a one-methylene group-higher homolog of arginine and to the guanidino derivative of lysine. L-Homoarginine is the naturally-occurring enantiomer. Physiologically, homoarginine increases nitric oxide (NO) supply and betters endothelial functions in the body, with a particular correlation and effect towards cardiovascular outcome and mortality. At physiological pH, homoarginine is cationic: the guanidino group is protonated.

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Homoarginine

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Homoarginine is an nonproteinogenic alpha-amino acid. It is structurally equivalent to a one-methylene group-higher homolog of arginine and to the guanidino...

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Lathyrus sativus

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due to toxicity. This legume is the only known dietary source for L-homoarginine[citation needed] and is preferred[by whom?] over arginine for nitric...

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Tears

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dimethylarginine/Symmetric dimethylarginine, Citrulline, Creatine, Glutamine, Homoarginine, Hydroxyproline, Phenylalanine, Proline, Pyroglutamic acid, Serine, Taurine...

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Alkaline phosphatase

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phosphatase isoenzymes except placental (PALP and SEAP) are inhibited by homoarginine, and, in similar manner, all except the intestinal and placental ones...

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Homocitrulline

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may be responsible for the enhanced synthesis of homocitrulline and homoarginine. Both amino acids can be detected in urine. Amino acid analysis allows...

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Phytotoxin

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modified tripeptide [Nδ-(N′-sulfodiaminophosphinyl)-ornithyl-alanyl-homoarginine] produced by certains strains of Pseudomonas syringae pv. phaseolicola...

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Endothelial NOS

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BOVINE ENDOTHELIAL NITRIC OXIDE SYNTHASE HEME DOMAIN COMPLEXED WITH HOMOARGININE (H4B FREE) 1dm8: BOVINE ENDOTHELIAL NITRIC OXIDE SYNTHASE HEME DOMAIN...

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Marta Bunster

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Bunster, M.; Wagner, K. G. (1975). "An X-ray diffraction study of poly-L-homoarginine hydrochloride". Biopolymers. 14 (6): 1197–1204. doi:10.1002/bip.1975...

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Perdur Radhakantha Adiga

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neurolathyrism in humans. He was also credited with the discovery of Homoarginine, an amino acid derivative, found in Lathyrus sativus. Later, he worked...

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