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Alliin

(S)-3-(2-Propenylsulfinyl)-L-alanine 3-[(S)-Allylsulfinyl]-L-alanine S-Allyl-L-cysteine sulfoxide | NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0

Alliin is a sulfoxide that is a natural constituent of fresh garlic.{{cite journal

Alliin was the first natural product found to have both carbon- and sulfur-centered stereochemistry.

Chemical synthesis

The first reported synthesis, by Stoll and Seebeck in 1951, begins the alkylation of L-cysteine with allyl bromide to form deoxyalliin. Oxidation of this sulfide with hydrogen peroxide gives both diastereomers of L-alliin, differing in the orientation of the oxygen atom on the sulfur stereocenter.

:[[File:H2O2toAlliin.png|left|frameless|420 px]]

A newer route, reported by Koch and Keusgen in 1998, allows stereospecific oxidation using conditions similar to the Sharpless asymmetric epoxidation. The chiral catalyst is produced from diethyl tartrate and titanium isopropoxide.

Medical exploration

Garlic has been used since antiquity for conditions now associated with oxidative stress (production and accumulation of reactive oxygen species (ROS)). In an in vitro test, garlic powder showed antioxidant properties, and alliin showed good hydroxyl radical-scavenging effect.{{cite journal

References

References

  1. (2001). "Intake of Garlic and Its Bioactive Components". Oxford University Press (OUP).
  2. Block, E. (2009). "Garlic and Other Alliums: The lore and the science". [[Royal Society of Chemistry]].
  3. (1951). "Chemical investigations on alliin, the specific principle of garlic".
  4. (1998). "Diastereoselective synthesis of alliin by an asymmetric sulfur oxidation". Pharmazie.
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alpha-amino-acids sulfoxides sulfur-amino-acids nutrition allyl-compounds
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