Chemistry:L-β-Homoleucine hydrochloride

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L-β-Homoleucine hydrochloride
L-β-Homoleucine hydrochloride.png
Names
IUPAC name
(3S)-3-Amino-5-methylhexanoic acid hydrochloride
Other names
H-BETA-HOMOLEU-OH HCL;H-BETA-HOLEU-OH HCL;H-LEU-(C*CH2)OH HCL;L-BETA-HOMOLEUCINE HCL;L-BETA-HOMOLEUCINE HYDROCHLORIDE;(S)-3-AMINO-5-METHYLHEXANOIC ACID HYDROCHLORIDE;L-β-homoleucine.HCI;H-β-homo-Leu-OH
Identifiers
3D model (JSmol)
8073252
Properties
C7H15NO2· HCl
Molar mass 181.66 g mol-1
Boiling point 249.1 °C
log P 0.90
Vapor pressure 0.00744 mmHg
Acidity (pKa) N/A
Hazards
Main hazards Flammable
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
1
0
Flash point 104.5°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

L-β-Homoleucine hydrochloride, also known as (3S)-3-Amino-5-methylhexanoic acid hydrochloride belongs to a class of unusual amino acids known as β-Homo amino acids or beta amino acids. The more common α-analogues of these amino acids are present in greater quantities and make up most polypeptides in a cell. β-amino acids however, can also be found in nature and bound to polypeptides, although at a reduced frequency. The hydrochloride is the chloride salt of the amino acid.

Properties

Homolecuine shares many of the same properties as its α-analogue lecuine. Some notable differences include being remarkably stable to metabolism, exhibiting slow microbial degradation, and inherently stable to proteases and peptidases, as well as folding into well-ordered secondary structures consisting of helices, turns, and sheets.[1][2][3][4]

References

  1. β-Amino Acids and Homologs, Aldrich ChemFiles 2008, 8.7, 11
  2. Wang, Pam Shou-Ping; Craig, Cody J.; Schepartz, Alanna (June 2012). "Relationship between side-chain branching and stoichiometry in β3-peptide bundles". Tetrahedron 68 (23): 4342–4345. doi:10.1016/j.tet.2012.03.079. 
  3. Zahradníčková, Helena; Jegorov, Alexandr; Trnka, Tomáš; Zelenka, Karel (January 2008). "Thiosugars - Derivatization agents for chiral resolution of homoleucines". Journal of Separation Science 31 (1): 133–136. doi:10.1002/jssc.200700208. 
  4. Ilisz, István; Berkecz, Robert; Péter, Antal (May 2008). "Application of chiral derivatizing agents in the high-performance liquid chromatographic separation of amino acid enantiomers: A review". Journal of Pharmaceutical and Biomedical Analysis 47 (1): 1–15. doi:10.1016/j.jpba.2007.12.013.