L-leucine
Leucine, derived from the ancient Greek word "λευκÏŒς" meaning white or bright, is an α-amino acid, with its IUPAC-IUBMB abbreviation denoted as Leu or L. It is one of the 22 proteinogenic amino acids, and one of the nine essential amino acids for humans. Leucine is classified as a branched-chain amino acid (BCAA), alongside valine and isoleucine.
Its encoding on mRNA occurs through the codons UUA, UUG, CUU, CUC, CUA, and CUG.
Upon cellular uptake, leucine can:
Regulate cellular processes, particularly stimulating muscle protein synthesis by activating the mammalian target of rapamycin complex 1 (mTORC1), a protein kinase. Be incorporated into a protein (proteinogenesis). Undergo degradation via the transfer of its amino group to α-ketoglutarate, following a transamination reaction. The final products of leucine metabolism in this third pathway are acetyl-CoA and acetoacetate. As such, it is classified as an exclusively ketogenic amino acid, along with lysine.
L-leucine has a sweet taste (with a detection threshold of 11–13 mmol·l-1) and is used in European food products as a flavor enhancer to amplify the taste of a food item. It is listed as a food additive under the number E641.
Accession Number : KLM0000248This work is released into the public domain; please see our release statement.
Synonyms :
- L-LEUCINE
- Leu
- L
Config Rule :
config('L-leucine',[
substituent(aminoacid_L_backbone),
substituent('buta-alpha-yl-beta-methyl'),
linkage(from(aminoacid_L_backbone,car(1)),
to('buta-alpha-yl-beta-methyl',car(1)),
down,single)]).
%%%% Substituent Config Rules for compound 'L-leucine' %%%%
config(aminoacid_L_backbone,[
left(amino),
right(hyd),
top(carboxyl),
center(car(1))]).
config('buta-alpha-yl-beta-methyl',[
top(methandiyl(1,empty)),
center(car(2,methyl&&hyd;)),
bottom(methyl)]).
Smiles String :
[C@2H]([NH3+])([C](=[O])[O-])[C@2H2][C@2H]([CH3])[CH3] 'L-leucine'
Fischer Diagram :
Terminal :
% 'L-leucine'
c(1,12,(0,chiral))-[n(1,left)~,h(1,right)~,c(2,up)~,c(3,down)~],
c(2,12,(0,nonchiral))-[o(1,nil)?,o(2,nil)?,c(1,down)~],
c(3,12,(0,nonchiral))-[c(4,left)~,h(9,right)~,c(1,up)~,h(10,down)~],
c(4,12,(0,nonchiral))-[c(5,left)~,c(3,right)~,h(5,up)~,c(6,down)~],
c(5,12,(0,nonchiral))-[h(6,left)~,c(4,right)~,h(7,up)~,h(8,down)~],
c(6,12,(0,nonchiral))-[h(11,left)~,h(13,right)~,c(4,up)~,h(12,down)~],
h(1,1,(0,nonchiral))-[c(1,left)~],
h(2,1,(0,nonchiral))-[n(1,right)~],
h(3,1,(0,nonchiral))-[n(1,down)~],
h(4,1,(0,nonchiral))-[n(1,up)~],
h(5,1,(0,nonchiral))-[c(4,down)~],
h(6,1,(0,nonchiral))-[c(5,right)~],
h(7,1,(0,nonchiral))-[c(5,down)~],
h(8,1,(0,nonchiral))-[c(5,up)~],
h(9,1,(0,nonchiral))-[c(3,left)~],
h(10,1,(0,nonchiral))-[c(3,up)~],
h(11,1,(0,nonchiral))-[c(6,right)~],
h(12,1,(0,nonchiral))-[c(6,up)~],
h(13,1,(0,nonchiral))-[c(6,left)~],
n(1,14,(1,nonchiral))-[h(2,left)~,c(1,right)~,h(3,up)~,h(4,down)~],
o(1,16,(-5.0E-01,nonchiral))-[c(2,nil)?],
o(2,16,(-5.0E-01,nonchiral))-[c(2,nil)?]
The Terminals for all the Config Rules are in Prolog Definite Clause Grammar (DCG) form.They can be checked in the Manual here.
The compound's PDB file can be seen here.