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H1007 Sigma-Aldrich

L-Homoarginine hydrochloride

unnatural arginine analog

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

  • CAS Number 1483-01-8

  • Linear Formula H2NC(=NH)NH(CH2)4CH(NH2)CO2H · HCl

  • Molecular Weight 224.69

  •  Beilstein/REAXYS Number 4016621

  •  EC Number 216-045-6

  •  MDL number MFCD00012622

  •  PubChem Substance ID 24895420

  •  NACRES NA.26

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Properties

Related Categories Amino Acids, Biochemicals and Reagents, Chemical Biology, Chemical Synthesis, Homo-Amino Acids,
Quality Level   200
assay   ≥98% (TLC)
form   powder
application(s)   peptide synthesis: suitable
color   white to off-white
mp   213-215 °C (lit.)
solubility   H2O: soluble
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

Description

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.

Packaging

5 g in poly bottle

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Related Content

Amino Acids Reference Charts

Amino acids are the compounds or building blocks that make up peptides and proteins. Each amino acid is structured from an amino group and a carboxyl group bound to a tetrahedral carbon. This carbon ...
Keywords: Building blocks, Gene expression, Mass spectrometry

Peer-Reviewed Papers
15

References

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