Alliin
- 1 min read
- 2 chapters
Related on Lably
Through Amino acid, Sulfur and Radical (chemistry)
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.
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.
Sign in to keep reading
One more chapter is free with a Lably account.
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. Alliin has also been found to affect immune responses in blood cells in vitro.