title: Encapsulation of Vitamin B(1) and Its Phosphate Derivatives by Cucurbit[7]uril: Tunability of the Binding Site and Affinity by the Presence of Phosphate Groups.
abstract: Vitamin B1 (1) and its phosphate derivatives, thiamine monophosphate (2) and thiamine pyrophosphate (3), are shown to form stable 1:1 host-guest complexes with cucurbit[7]uril (CB[7]) in aqueous solution. The binding sites of CB[7] on these guests shift from the ethylthiazolium region of 1 to the pyrimidine moiety of 2 and 3 due to the presence of phosphate groups, leading to variations of binding affinities as well as C(2)-H/D exchange rate constants and C(2)-H pKa values with these guest molecules.
authors.affiliation: State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.
authors.forename: Shengke
authors.initials: S
authors.lastname: Li
authors.affiliation: State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.
authors.forename: Hang
authors.initials: H
authors.lastname: Yin
authors.affiliation: Department of Chemistry, Queen's University , 90 Bader Lane, Kingston, ON K7L 3N6, Canada.
authors.forename: Ian W
authors.initials: IW
authors.lastname: Wyman
authors.affiliation: State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.
authors.forename: Qingwen
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, Queen's University , 90 Bader Lane, Kingston, ON K7L 3N6, Canada.
authors.forename: Donal H
authors.initials: DH
authors.lastname: Macartney
authors.affiliation: State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.
authors.forename: Ruibing
authors.initials: R
authors.lastname: Wang
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010710:Phosphates / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013831:Thiamine / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
chemical_list: D001952:Bridged-Ring Compounds; D003903:Deuterium; D007093:Imidazoles; D010710:Phosphates; D011743:Pyrimidines; D013831:Thiamine; D013844:Thiazoles; C456276:cucurbit(7)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils