Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2-sec-Butyl-4,5-dihydrothiazole: Difference between pages

{{DISPLAYTITLE:2-''sec''-Butyl-4,5-dihydrothiazole}}

| Verifiedfields = changed

| verifiedrevid = 477344176

| PubChem|162148}}</ref>

| = 2-(Butan-2-yl)-4,5-dihydro-1,3-thiazole

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 56367-27-2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C7H13NS/c1-3-6(2)7-8-4-5-9-7/h6H,3-5H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 142398

| = 70.5

}}

| Section4 = {{Chembox Related

| OtherCompounds = [[Dihydrothiazole]] (thiazoline)

'''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 [[rat]]s, SBT is excreted in the urine and promotes aggression amongst males while inducing synchronized estrus in females.<ref>{{cite journal | doi = 10.1002/pro.426 | title = High resolution X-ray structures of mouse major urinary protein nasal isoform in complex with pheromones | year = 2010 | last1 = Perez-Miller | first1 = Samantha | last2 = Zou | first2 = Qin | last3 = Novotny | first3 = Milos V. | last4 = Hurley | first4 = Thomas D. | journal = Protein Science | volume = 19 | issue = 8 | pages = 1469–79 | pmid = 20509168 | pmc = 2923500}}</ref>

==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. <ref>{{cite journal | doi = 10.1110/ps.52201 | title = Structural basis of pheromone binding to mouse major urinary protein (MUP-I) | year = 2001 | last1 = Timm | first1 = David E. | last2 = Baker | first2 = L.J. | last3 = Mueller | first3 = Heather | last4 = Zidek | first4 = Lukas | last5 = Novotny | first5 = Milos V. | journal = Protein Science | volume = 10 | issue = 5 | pages = 997–1004 | pmid = 11316880 | pmc = 2374202}}</ref>

== Synthesis ==

SBT can be produced from 3-(2-aminoethanethio)-4-methylhex-2-enenitrile;<ref>{{cite journal | doi = 10.1016/S0040-4020(01)88457-X | title = Allenes-41 the addition of thiols to allenyl- and phenylpropynyl- nitrile and the formation of thiazolines and benzothiazoles | year = 1984 | last1 = Landor | first1 = S | journal = Tetrahedron | volume = 40 | issue = 11 | pages = 2141}}</ref> however, it is also possible to synthesize SBT from [[ethanolamine]] and [[2-methylbutanoic acid]], using [[Lawesson's reagent]] and [[microwave irradiation]].<ref>{{cite journal | doi = 10.1016/j.tet.2008.07.027 | title = Straightforward microwave-assisted synthesis of 2-thiazolines using Lawesson's reagent under solvent-free conditions | year = 2008 | last1 = Seijas | first1 = Julio A. | last2 = Vázquez-Tato | first2 = M. Pilar | last3 = Crecente-Campo | first3 = José | journal = Tetrahedron | volume = 64 | issue = 39 | pages = 9280}}</ref>

== References ==

<references />

{{DEFAULTSORT:Butyl-4,5-dihydrothiazole, 2-sec-}}

[[Category:Mammalian pheromones]]

[[Category:Thiazolines]]

[[Category:Sec-Butyl compounds]]