Chemistry:Leucines

From HandWiki

The leucines are primarily the four isomeric amino acids: leucine, isoleucine, tert-leucine (terleucine, pseudoleucine) and norleucine.[1] Being compared with the four butanols, they could be classified as butyl-substituted glycines; they represent all four possible variations. Leucine and isoleucine belong to the proteinogenic amino acids; the others are non-natural.

Isomers

Including the stereoisomers, six further isomers could be added: D-leucine, D-isoleucine, L-alloisoleucine, D-alloisoleucine, D-tert-leucine and D-norleucine.

Leucines
Name L-Leucine L-Isoleucine L-tert-Leucine (terleucine, pseudoleucine) L-Norleucine
Other names 2-Amino-4-methylpentanoic acid,
Isobutylglycine
2-Amino-3-methylpentanoic acid,
sec-Butylglycine
2-Amino-3,3-dimethylbutanoic acid,
tert-Butylglycine
2-Amino-hexanoic acid,
n-Butylglycine
Structure L-Leucin - L-Leucine.svg 150px 110px L-Norleucin.svg
CAS-number 61-90-5 73-32-5 20859-02-3 327-57-1
PubChem CID 6106 from PubChem CID 791 from PubChem CID 164608 from PubChem CID 21236 from PubChem
Molecular formula C6H13NO2
Molar mass 131.18 g/mol

Derivatives

Cycloleucine could be classified as a cyclic derivative of norleucine. With a cyclopentane-ring, it has two hydrogen atoms fewer and thus is not an isomer. The α-carbon atom is not a stereocenter.

Cycloleucine

See also


Literature

  • Jeremy M. Berg, John L. Tymoczko, Lubert Stryer: Biochemie. 6 Auflage, Spektrum Akademischer Verlag, Heidelberg 2007. ISBN:978-3-8274-1800-5.
  • Donald Voet, Judith G. Voet: Biochemistry. 3. Auflage, John Wiley & Sons, New York 2004. ISBN:0-471-19350-X.
  • Bruce Alberts, Alexander Johnson, Peter Walter, Julian Lewis, Martin Raff, Keith Roberts: Molecular Biology of the Cell, 5. Auflage, Taylor & Francis 2007, ISBN:978-0815341062.

References

  1. Zaremska, Valeriia; Tan, Jiajun; Lim, Sierin; Knoll, Wolfgang; Pelosi, Paolo (2020-07-17). "Isoleucine Residues Determine Chiral Discrimination of Odorant‐Binding Protein" (in en). Chemistry – A European Journal 26 (40): 8720–8724. doi:10.1002/chem.202000872. ISSN 0947-6539. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202000872.