β-Leucine

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β-Leucine
Β-leucine.svg
Names
IUPAC name
3-Amino-4-methylpentanoic acid
Other names
DL-β-Leucine; Homovaline
Identifiers
3D model (JSmol)
3DMet B00449
ChEBI
ChemSpider
ECHA InfoCard 100.200.152
KEGG
Properties
C6H13NO2
Molar mass 131.175 g·mol−1
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

β-Leucine (beta-leucine) is a beta amino acid and positional isomer of L-leucine which is naturally produced in humans via the metabolism of L-leucine by the enzyme leucine 2,3-aminomutase.[1][2][3] In cobalamin (vitamin B12) deficient individuals, plasma concentrations of β-leucine are elevated.[3]

Biosynthesis and metabolism in humans[edit]

A small fraction of L-leucine metabolism – less than 5% in all tissues except the testes where it accounts for about 33% – is initially catalyzed by leucine aminomutase, producing β-leucine, which is subsequently metabolized into β-ketoisocaproate (β-KIC), β-ketoisocaproyl-CoA, and then acetyl-CoA by a series of uncharacterized enzymes.[1][2]

References[edit]

  1. ^ a b Kohlmeier M (May 2015). "Leucine". Nutrient Metabolism: Structures, Functions, and Genes (2nd ed.). Academic Press. pp. 385–388. ISBN 978-0-12-387784-0. Archived from the original on 22 March 2018. Retrieved 6 June 2016. Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds
    Figure 8.57: Metabolism of L-leucine Archived 22 March 2018 at the Wayback Machine
  2. ^ a b "Leucine metabolism". BRENDA. Technische Universität Braunschweig. Archived from the original on 17 August 2016. Retrieved 12 August 2016.
  3. ^ a b http://www.hmdb.ca/metabolites/HMDB03640