β-Homoleucine, also known as 3-amino-5-methylhexanoic acid, 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. β-Homoleucine can exists as either of two enantiomers, D-β-homoleucine and L-β-homoleucine, with L-β-homoleucine being the more common isomer. β-Homoleucine hydrochloride is the hydrochloride salt of the amino acid.

β-Homoleucine

L-β-homoleucine
Names
IUPAC name
3-Amino-5-methylhexanoic acid
Other names
H-BETA-HOMOLEU-OH; H-BETA-HOLEU-OH; H-β-homo-Leu-OH
Identifiers
3D model (JSmol)
8073252
  • Key: MLYMSIKVLAPCAK-UHFFFAOYSA-N
  • (DL): InChI=1S/C7H15NO2/c1-5(2)3-6(8)4-7(9)10/h5-6H,3-4,8H2,1-2H3,(H,9,10)
  • (DL): CC(C)CC(CC(=O)O)N
Properties
C7H15NO2
Molar mass 145.202 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
GHS labelling:
GHS07: Exclamation mark
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Properties

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Homolecuine shares many of the same properties as its α-analogue leucine. Some notable differences include being remarkably stable to metabolism, exhibiting slow microbial degradation, and being 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

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  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. PMC 3398705. PMID 22822272.
  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. PMID 18080246.
  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. PMID 18242036.