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L-β-Homoleucine hydrochloride[edit]

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.

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
8073252
Properties
C7H15NO2· HCl
Molar mass 181.66 g mol-1
Appearance N/A
Density N/A cm-3
Melting point N/A
Boiling point 249.1 °C
N/A L-1
Solubility in ethanol N/A
log P 0.90
Vapor pressure 0.00744 mmHg
Acidity (pKa) N/A
Hazards
Main hazards Flammable
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen NFPA 704 four-colored diamond

S=0 NFPA code error
.
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):

Properties[edit]

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.

Occurrences[edit]

|Amino Acids play a critical part in the formation of any given protein in a cell. Proteins are required for cellular function and have many specific jobs in a given cell. Amino acids are the subunits that make up a polypeptide and are referred to as the polpypeptides primary sequence.β-amino acids are an unusual type of amino acid that is found in cell but at aa greatly reduced frequency when compared to their α-analogues.β-amino acids are remarkably stable to metabolize, exhibiting slow microbial degradation, and inherently stable to proteases and peptidases, they fold into well-ordered secondary structures consisting of helices, turns, and sheets[reference1]

History[edit]

Homoleucine, like all of the unusual amino acid, has recently come into the focus of research and as a result does not contain significant history.

Production[edit]

A whole new “world” has emerged from the design of fascinating new peptidic macromolecules from β- and γ-homologated proteinogenic amino acids and other components. These compounds are now used to construct polypeptides and study the proteins that result from them.

Reactions[edit]

Homolecuine participates in a Peptide bond that links various amino acids together to form a polypeptide.

Uses[edit]

Homoleucine is used as a substrate Amino acid in the synthesis of polypeptides from which proteins are derived.

Safety[edit]

Protective eye ware and equipment should be worn to avoid direct contact. Do not store with incompatible materials such as oxidizing agents, reducing agents, bases, alkali metals.

References[edit]

1. β-Amino Acids and Homologs, Aldrich ChemFiles 2008, 8.7, 11.

2. Wang PS, Craig CJ, Schepartz A. Tetrahedron. 2012 Jun 10;68(23):4342-4345.

3. Zahradnícková H, Jegorov A, Trnka T, Zelenka K., J Sep Sci. 2008 Jan;31(1):133-6.

4. Ilisz I, Berkecz R, Péter A., J Pharm Biomed Anal. 2008 May 12;47(1):1-15. Epub 2007 Dec 15.