β-Leucine

β-Leucine
Names
	Preferred IUPAC name 3-Amino-4-methylpentanoic acid
	Other names DL-β-Leucine; Homovaline
Identifiers
CAS Number	5699-54-7;
3D model (JSmol)	Interactive image;
3DMet	B00449;
ChEBI	CHEBI:15604;
ChemSpider	167837;
ECHA InfoCard	100.200.152
KEGG	C02486;
PubChem CID	2761558;
CompTox Dashboard (EPA)	DTXSID50863602 ;
	InChI InChI=1S/C6H13NO2/c1-4(2)5(7)3-6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9) Key: GLUJNGJDHCTUJY-UHFFFAOYSA-N;
	SMILES CC(C)C(CC(=O)O)N;
Properties
Chemical formula	C6H13NO2
Molar mass	131.175 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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

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

^ ^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
^ ^a ^b "Leucine metabolism". BRENDA. Technische Universität Braunschweig. Archived from the original on 17 August 2016. Retrieved 12 August 2016.
^ ^a ^b "Human Metabolome Database: Showing metabocard for Beta-Leucine (HMDB0003640)".

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[Leucine_metabolism-1] 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

[BRENDA_leucine_metabolism-2] "Leucine metabolism". BRENDA. Technische Universität Braunschweig. Archived from the original on 17 August 2016. Retrieved 12 August 2016.

[HMDB_β-Leucine-3] "Human Metabolome Database: Showing metabocard for Beta-Leucine (HMDB0003640)".

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[2]

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