In vitro stability and chemical reactivity of thiosulfinates.
A model reaction system was used to generate pure thiosulfinates (3) from S-alk(en)yl-L-cysteine sulfoxides (1) to facilitate studies on the intrinsic pH and thermal sensitivities of individual thiosulfinate species. Thiosulfinate decay could be characterized as first-order processes over the pH range of 1.2-9.0 and at 20-80 degrees C. The stability of thiosulfinates was greatest at pH 4.5-5.5, followed by pH 1.2, pH 6.5-7.5, and pH 8.0-9.0. Thiosulfinates with longer and saturated alk(en)yl groups were generally more stable than those with shorter and unsaturated alk(en)yl groups. Thiosulfinates underwent thioalkyl-exchange reactions at pH 8-9 without loss of total thiosulfinate levels within 60-90 min at 20 degrees C.
Shen
Cunxi
C
University of Wisconsin-Madison, Department of Food Science, Babcock Hall, 1605 Linden Drive, Madison, WI 53706, USA.
Xiao
Hang
H
Parkin
Kirk L
KL
D000490:Allium / Q000737:chemistry; D013437:Carbon-Sulfur Lyases / Q000378:metabolism; D004355:Drug Stability; D004800:Enzymes, Immobilized; D006358:Hot Temperature; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D013441:Sulfinic Acids / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D004800:Enzymes, Immobilized; D013441:Sulfinic Acids; C100040:thiosulfinic acids; D014867:Water; D013437:Carbon-Sulfur Lyases; C019243:alliin lyase