Английская Википедия:2-sec-Butyl-4,5-dihydrothiazole
2-sec-Butyl-4,5-dihydrothiazole (also known as SBT) is a thiazoline compound with the molecular formula C7H13NS. A volatile pheromone found in rodents such as mice and rats, SBT is excreted in the urine and promotes aggression amongst males while inducing synchronized estrus in females.[1]
Binding to MUP
Mouse major urinary proteins (MUPs) are responsible for binding to hydrophobic ligands such as the pheromone SBT. SBT binds within MUP-I's barrel-shaped active site, forming a hydrogen bond with a water molecule within the active site, which in turn is stabilized by forming hydrogen bonds with residue Phe56 and another water molecule; this second water molecule also forms hydrogen bonds to residues in the active site, namely Leu58 and Thr39. SBT also forms van der Waals forces with several of MUP-I's residues, including Ala121, Leu123, Leu134, Leu72, Val100, and Phe108.
When bound, MUP safely carries SBT through the aqueous environment; once the protein-ligand complex is excreted in the urine, MUP helps prevent SBT decomposition and controls the slow release of SBT over a prolonged period of time, resulting in the physiological and behavioral responses of animals who come into contact with the pheromone. [2]
Synthesis
SBT can be produced from 3-(2-aminoethanethio)-4-methylhex-2-enenitrile;[3] however, it is also possible to synthesize SBT from ethanolamine and 2-methylbutanoic acid, using Lawesson's reagent and microwave irradiation.[4]
References
