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Alloisoleucine

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

Structure

Together with valine, leucine, and isoleucine, alloisoleucine is classified as a branched-chain amino acid (BCAA). It is the rarest of the four.

L-Alloisoleucine is a diastereomer of the proteogenic amino acid L-isoleucine. The stereochemistry of the isobutyl group differs for L-alloisoleucine and L-isoleucine.

Role in biosynthesis

L-allo-isoleucine is a precursor to coronamic acid, which is a constituent of the phytotoxin coronatine, produced by Pseudomonas syringae.[2]

References

  1. ^ Schadewaldt, Peter; Bodner-Leidecker, Annette; Hammen, Hans-Werner; Wendel, Udo (2000). "Formation of L-Alloisoleucine in Vivo : An L-[13C]Isoleucine Study in Man". Pediatric Research. 47 (2): 271–277. doi:10.1203/00006450-200002000-00020. PMID 10674358. S2CID 530588.
  2. ^ Vaillancourt, Frédéric H.; Yeh, Ellen; Vosburg, David A.; O'Connor, Sarah E.; Walsh, Christopher T. (August 2005). "Cryptic chlorination by a non-haem iron enzyme during cyclopropyl amino acid biosynthesis". Nature. 436 (7054): 1191–1194. Bibcode:2005Natur.436.1191V. doi:10.1038/nature03797. ISSN 1476-4687. PMID 16121186. S2CID 4428247.