Β-Homoleucine

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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
ChEBI
ChemSpider
EC Number
  • (DL): 676-223-8
  • (D): 676-223-8
  • (L): 674-652-5
UNII
  • 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)
  • (D): InChI=1S/C7H15NO2/c1-5(2)3-6(8)4-7(9)10/h5-6H,3-4,8H2,1-2H3,(H,9,10)/t6-/m1/s1
    Key: MLYMSIKVLAPCAK-ZCFIWIBFSA-N
  • (L): InChI=1S/C7H15NO2/c1-5(2)3-6(8)4-7(9)10/h5-6H,3-4,8H2,1-2H3,(H,9,10)/t6-/m0/s1
    Key: MLYMSIKVLAPCAK-LURJTMIESA-N
  • (DL): CC(C)CC(CC(=O)O)N
  • (D): CC(C)C[C@H](CC(=O)O)N
  • (L): CC(C)C[C@@H](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).
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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]

References

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