20736-40-7Relevant academic research and scientific papers
Probing the Binding Pocket of the Broadly Tuned Human Bitter Taste Receptor TAS2R14 by Chemical Modification of Cognate Agonists
Karaman, Rafik,Nowak, Stefanie,Di Pizio, Antonella,Kitaneh, Hothaifa,Abu-Jaish, Alaa,Meyerhof, Wolfgang,Niv, Masha Y.,Behrens, Maik
, p. 66 - 75 (2016)
Sensing potentially harmful bitter substances in the oral cavity is achieved by a group of ?25 receptors, named TAS2Rs, which are expressed in specialized sensory cells and recognize individual but overlapping sets of bitter compounds. The receptors differ in their tuning breadths ranging from narrowly to broadly tuned receptors. One of the most broadly tuned human bitter taste receptors is the TAS2R14 recognizing an enormous variety of chemically diverse synthetic and natural bitter compounds, including numerous medicinal drugs. This suggests that this receptor possesses a large readily accessible ligand binding pocket. To allow probing the accessibility and size of the ligand binding pocket, we chemically modified cognate agonists and tested receptor responses in functional assays. The addition of large functional groups to agonists was usually possible without abolishing agonistic activity. The newly synthesized agonist derivatives were modeled in the binding site of the receptor, providing comparison to the mother substances and rationalization of the in vitro activities of this series of compounds.
Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
Fang, Jing,Li, Ting,Ma, Xiang,Sun, Jiuchang,Cai, Lei,Chen, Qi,Liao, Zhiwen,Meng, Lingkui,Zeng, Jing,Wan, Qian
, p. 288 - 292 (2021/07/25)
A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.
Acyclic 1,4-Stereocontrol via the Allylic Diazene Rearrangement: Development, Applications, and the Essential Role of Kinetic e Stereoselectivity in Tosylhydrazone Formation
Shrestha, Maha L.,Qi, Wei,McIntosh, Matthias C.
, p. 8359 - 8370 (2017/08/23)
We report full details of a method for 1,3-reductive transposition of α-alkoxy-α,β-unsaturated hydrazones to provide E-alkenes with high 1,4-stereocontrol between the two respective allylic stereocenters. The process couples a chelation-controlled reduction of the hydrazone with an in situ allylic strain controlled retro-ene reaction of an allyl diazene, i.e., an allylic diazene rearrangement. Such stereotriads are frequently observed motifs in natural products. We observed a fortuitous kinetic preference for the E-hydrazone geometry during the hydrazonation reaction, as only the E-isomers could undergo chelation-controlled reduction.
Counterattack mode differential acetylative deprotection of phenylmethyl ethers: Applications to solid phase organic reactions
Chakraborti, Asit K.,Chankeshwara, Sunay V.
supporting information; experimental part, p. 1367 - 1370 (2009/07/04)
A counterattack protocol for differential acetylative cleavage of phenylmethyl ether has been developed. The phenylmethyl moiety is liberated as benzyl bromide that is isolated and reused providing advantages in terms of waste minimization/utilization and atom economy. The applicability of this methodology has been extended for solid phase organic reactions with the feasibility of reuse of the solid support.
