Β-Homoleucine Explained

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.

Properties

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]

Notes and References

  1. β-Amino Acids and Homologs, Aldrich ChemFiles 2008, 8.7, 11
  2. Wang . Pam Shou-Ping . Craig . Cody J. . Schepartz . Alanna . Relationship between side-chain branching and stoichiometry in β3-peptide bundles . Tetrahedron . June 2012 . 68 . 23 . 4342–4345 . 10.1016/j.tet.2012.03.079. 22822272 . 3398705 .
  3. Zahradníčková . Helena . Jegorov . Alexandr . Trnka . Tomáš . Zelenka . Karel . Thiosugars - Derivatization agents for chiral resolution of homoleucines . Journal of Separation Science . January 2008 . 31 . 1 . 133–136 . 10.1002/jssc.200700208. 18080246 .
  4. Ilisz . István . Berkecz . Robert . Péter . Antal . Application of chiral derivatizing agents in the high-performance liquid chromatographic separation of amino acid enantiomers: A review . Journal of Pharmaceutical and Biomedical Analysis . May 2008 . 47 . 1 . 1–15 . 10.1016/j.jpba.2007.12.013. 18242036 .