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Selected Chemistry Of Biologically-Active Thiols : N-Acetylpenicillamine And 2-Mercaptobenzothiazole In Nitrosothiol Formation And Role In Allergic Contact Dermatitis Respectively, Itai Chipinda
Dissertations and Theses
Two biologically-active thiols, N-acetylpenicillamine (NAP) and 2-mercaptobenzothiazole (MBT), were studied in this thesis. NAP is known to combine with nitric oxide (NO) to produce S-nitroso-N-acetylpenicillamine (SNAP) and MBT is a known allergen.
The formation, reaction dynamics, and detailed kinetics and mechanism of the reaction between nitrous acid (HNO2), prepared in situ, and NAP to produce SNAP were studied. The reaction is first order in nitrite, NAP and acid in pH conditions at or slightly higher than the pKa of HNO2. Both HPLC and quadrupole time-of-flight mass spectrometry techniques confirmed the formation of SNAP and the absence of any other products. …