57093-66-0Relevant academic research and scientific papers
Carbon chain shape selectivity by the mouse olfactory receptor OR-I7
Liu, Min Ting,Ho, Jianghai,Liu, Jason Karl,Purakait, Radhanath,Morzan, Uriel N.,Ahmed, Lucky,Batista, Victor S.,Matsunami, Hiroaki,Ryan, Kevin
, p. 2541 - 2548 (2018/04/12)
The rodent OR-I7 is an olfactory receptor exemplar activated by aliphatic aldehydes such as octanal. Normal alkanals shorter than heptanal bind OR-I7 without activating it and hence function as antagonists in vitro. We report a series of aldehydes designed to probe the structural requirements for aliphatic ligand chains too short to meet the minimum approximate 6.9 ? length requirement for receptor activation. Experiments using recombinant mouse OR-I7 expressed in heterologous cells show that in the context of short aldehyde antagonists, OR-I7 prefers binding aliphatic chains without branches, though a single methyl on carbon-3 is permitted. The receptor can accommodate a surprisingly large number of carbons (e.g. ten in adamantyl) as long as the carbons are part of a conformationally constrained ring system. A rhodopsin-based homology model of mouse OR-I7 docked with the new antagonists suggests that small alkyl branches on the alkyl chain sterically interfere with the hydrophobic residues lining the binding site, but branch carbons can be accommodated when tied back into a compact ring system like the adamantyl and bicyclo[2.2.2]octyl systems.
Synthesis and Properties of Some tert-Alkylmalonic Acid Derivatives
Holmberg, Carl
, p. 748 - 760 (2007/10/02)
1,4-Addition of Grignard reagents to the alkylidenemalonic acid derivatives 1-8 affords the tert-alkyl malonic derivatives 9-18.The esters 9-17 give the acids 19-26 and from these the corresponding chlorides 27-34 are obtained.Bromination yields the bromo acids 35-36, the brominated acyl bromide 43, the bromonitrile 44, and the bromoacyl chlorides 37-42.The trimethylsilyl esters 50-52, the bis(2-bromoethyl) esters 53-54, the ethyl ester 14, and the tert-butyl ester 16 are brominated via the corresponding ester enolates giving the bromo esters 45-46 in pure form. - The dealkylation of malonic esters with chlorotrimethylsilane/sodium iodide has been carried out.
