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L-leucine

Leucine, derived from the ancient Greek word "λευκός" 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.

MBS358036 | Polyclonal anti-conjugated L-leucine antibodies
MBS358306 | L-Leucine (BSA) conjugate
MBS405063 | L-Leucine
MBS407412 | N-Formyl-L-Leucine
MBS546014 | L-Leucine
MBS614552 | L-Leucine, Conjugated
MBS6031881 | N-tert-Butylcarbamoyl-L-tert-leucine
MBS6036935 | Gly-Leu (Glycyl-L-leucine)
MBS6044580 | L-Leucine (non-animal)
MBS6046966 | N-(Methoxycarbonyl)-L-tert-leucine
MBS6074061 | tert-Butoxycarbonyl-L-leucine
MBS6074896 | N-tert-Butoxycarbonyl-L-tert-leucine
MBS6084554 | N-Formyl-L-leucine
MBS6100726 | Cbz-L-tert-Leucine
MBS6104940 | L-Leucine-d3
MBS6120471 | N-Formyl-L-leucine-d3
MBS3608902 | L-Leucine
MBS3609542 | N-Acetyl-L-leucine
MBS4158169 | Anti-Conjugated L-Leucine Antibody
MBS5750287 | L-Leucine

 

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.