Selective oxidation of allylic alcohols with chromic acid

Harding, Kenn E.; May, Leslie M.; DICK, K. F.

doi:10.1021/jo00899a040

Cited by 83 publications

(34 citation statements)

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“…We found that all four different isotopomers of 1 gave highly similar responses and the EC 50 values of the respective dose-response curves were not significantly different (Fig. 3A, Left, and SI Appendix, Table S3.2A).…”

Section: Response Of a Human Musk Or To Deuterated And Nondeuteratedmentioning

confidence: 79%

“…One-way ANOVA or an unpaired Student's t test was used to compare the 95% confidence interval logEC 50 values among isotopomers for each receptor/odorant pair in Figs. 3 and 4.…”

Section: Methodsmentioning

confidence: 99%

“…The level of significance was *P < 0.05. An F test was used to compare the best-fit values of EC 50 , Hill slope, and top of the dose-response curves between the original hydrogenated odorant and its isotopomers in Figs. 3 and 4 and SI Appendix, Fig.…”

Section: Methodsmentioning

confidence: 99%

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Implausibility of the vibrational theory of olfaction

Block

Jang

Matsunami

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

115

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The vibrational theory of olfaction assumes that electron transfer occurs across odorants at the active sites of odorant receptors (ORs), serving as a sensitive measure of odorant vibrational frequencies, ultimately leading to olfactory perception. A previous study reported that human subjects differentiated hydrogen/ deuterium isotopomers (isomers with isotopic atoms) of the musk compound cyclopentadecanone as evidence supporting the theory. Here, we find no evidence for such differentiation at the molecular level. In fact, we find that the human musk-recognizing receptor, OR5AN1, identified using a heterologous OR expression system and robustly responding to cyclopentadecanone and muscone, fails to distinguish isotopomers of these compounds in vitro. Furthermore, the mouse (methylthio)methanethiol-recognizing receptor, MOR244-3, as well as other selected human and mouse ORs, responded similarly to normal, deuterated, and 13 C isotopomers of their respective ligands, paralleling our results with the musk receptor OR5AN1. These findings suggest that the proposed vibration theory does not apply to the human musk receptor OR5AN1, mouse thiol receptor MOR244-3, or other ORs examined. Also, contrary to the vibration theory predictions, muscone-d 30 lacks the 1,380-to 1,550-cm −1 IR bands claimed to be essential for musk odor. Furthermore, our theoretical analysis shows that the proposed electron transfer mechanism of the vibrational frequencies of odorants could be easily suppressed by quantum effects of nonodorant molecular vibrational modes. These and other concerns about electron transfer at ORs, together with our extensive experimental data, argue against the plausibility of the vibration theory.olfaction | isotopomers | cyclopentadecanone | muscone | electron transfer I n 1870, the British physician William Ogle wrote: "As in the eye and the ear the sensory impression is known to result not from the contact of material particles given off by the object seen or heard, but from waves or undulations of the ether or the air, one cannot but suspect that the same may be true in the remaining sense, and that the undulatory theory of smell. . . [may be] the true one" (1, 2). Of the 29 different "theories of odour" listed in the 1967 edition of The Chemical Senses (3), nine associate odor with vibrations, particularly those theories championed by Dyson (4, 5) and Wright (6-8). However, the premise that olfaction involves detection of vibrational frequencies of odorants remains highly speculative because neither the structures of the odorant receptors (ORs) nor the binding sites or the activation mechanisms triggered upon odorant binding to ORs have been established. In 1996-1997, Turin (9-12) elaborated on the undulatory theory of smell, as considered in more detail below, and suggested that a mechanism analogous to inelastic electron tunneling spectroscopy (13) may be involved, where tunneling electrons in the receptor probe the vibrational frequencies of odorants. In 2013, Gane et al. (14) In judging the plausibility...

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Section: Response Of a Human Musk Or To Deuterated And Nondeuteratedmentioning

confidence: 79%

“…One-way ANOVA or an unpaired Student's t test was used to compare the 95% confidence interval logEC 50 values among isotopomers for each receptor/odorant pair in Figs. 3 and 4.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Implausibility of the vibrational theory of olfaction

Block

Jang

Matsunami

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

115

View full text Add to dashboard Cite

show abstract

“…The necessary, enantiopure (aS)-2Ј-methoxy-1,1Ј-binaphthyl-2-carboxyaldehyde (1) was prepared following the procedure reported by Miyano: [11] the pure diastereoisomeric binaphthylic menthol ester was reduced to the alcohol by LiAlH 4 and then oxidised to the aldehyde by JonesЈ reagent [12] (Scheme 1).…”

Section: Synthesismentioning

confidence: 99%

Chiral Atropisomeric Metalloporphyrins in the Enantioselective Styrene Epoxidation

Reginato

Bari

Salvadori³

et al. 2000

Eur. J. Org. Chem.

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“…9 Finally the alcohol 5 was oxidized by the Jones reagent, 10 In a typical procedure for the Prins cyclization reaction, 2.70 g of aluminum chloride (20.2 mmol) is added to a flame-dried flask, where 10 mL of dichloromethane (dried under calcium hydride), is added. To this flask, a solution containing 3.5 g (20.2 mmol) of homoallylic alcohol 3, 1.5 mL (20.2 mmol) of propanal, in 6 mL of dichloromethane is slowly added at 0 C. The reaction mixture is left stirring at this temperature for 2.5 h. After this time, 5 mL of a saturated sodium bicarbonate solution is slowly added until pH 7.…”

Section: Chemistrymentioning

confidence: 99%