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Alloisoleucine

Chemical compound From Wikipedia, the free encyclopedia

Alloisoleucine is an amino acid with the formula CH3CH2CH(CH3)CH(NH2)CO2H. It is the diastereomer of isoleucine, differing in the stereochemistry within the side chain. Alloisoleucine exists as two enantiomers, of which the L isomer occurs naturally. L-Alloisoleucine occurs in healthy serum in only trace amounts, except for individuals suffering from maple syrup urine disease.[1]

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Alloisoleucine
Identifiers
3D model (JSmol)
1721791
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.014.676 Edit this at Wikidata
EC Number
  • L: 216-142-3
  • racemic: 207-139-8
UNII
  • InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5+/m1/s1
    Key: AGPKZVBTJJNPAG-UHNVWZDZSA-N
  • D: InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5+/m0/s1
    Key: AGPKZVBTJJNPAG-CRCLSJGQSA-N
  • L: CC[C@@H](C)[C@@H](C(=O)O)N
  • D: CC[C@H](C)[C@H](C(=O)O)N
  • racemic: CCC(C)C(C(=O)O)N
Properties
C6H13NO2
Molar mass 131.175 g·mol−1
Appearance white solid
Melting point 285 °C (545 °F; 558 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Structure

Together with valine, leucine, and isoleucine, alloisoleucine is classified as a branched-chain amino acid (BCAA). The L enantiomer of valine, leucine, and isoleucine are proteinogenic amino acids; alloisoleucine is non-proteinogenic.

 
l-isoleucine (2S,3S) and d-isoleucine (2R,3R)
 
l-alloisoleucine (2S,3R) and d-alloisoleucine (2R,3S)

Role in biosynthesis

L-Alloisoleucine is a precursor to coronatine, a phytotoxin produced by Pseudomonas syringae.[2]

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