Facile synthesis of 4-acetoxy-2-methyl-2-butenal, a vitamin A precursor, from isoprene chlorohydrin

Babler, James H.; Coghlan, Michael J.; M, Feng; Fries, Peter

doi:10.1021/jo01324a030

Cited by 22 publications

(10 citation statements)

References 1 publication

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“…13 C NMR (101 MHz, CDCl 3 ) δ 170.4, 136.6, 123.5, 60.4, 50.5, 20.5, 14.2. Spectroscopic data for H-NMR are in agreement with those reported ( 30 ).…”

Section: Methodssupporting

confidence: 89%

Clickable Vitamins as a New Tool to Track Vitamin A and Retinoic Acid in Immune Cells

et al. 2021

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The vitamin A derivative, retinoid acid (RA) is key player in guiding adaptive mucosal immune responses. However, data on the uptake and metabolism of vitamin A within human immune cells has remained largely elusive because retinoids are small, lipophilic molecules which are difficult to detect. To overcome this problem and to be able to study the effect of vitamin A metabolism in human immune cell subsets, we have synthesized novel bio-orthogonal retinoid-based probes (clickable probes), which are structurally and functionally indistinguishable from vitamin A. The probes contain a functional group (an alkyne) to conjugate to a fluorogenic dye to monitor retinoid molecules in real-time in immune cells. We demonstrate, by using flow cytometry and microscopy, that multiple immune cells have the capacity to internalize retinoids to varying degrees, including human monocyte-derived dendritic cells (DCs) and naïve B lymphocytes. We observed that naïve B cells lack the enzymatic machinery to produce RA, but use exogenous retinoic acid to enhance CD38 expression. Furthermore, we showed that human DCs metabolize retinal into retinoic acid, which in co-culture with naïve B cells led to of the induction of CD38 expression. These data demonstrate that in humans, DCs can serve as an exogenous source of RA for naïve B cells. Taken together, through the use of clickable vitamins our data provide valuable insight in the mechanism of vitamin A metabolism and its importance for human adaptive immunity.

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“…13 C NMR (101 MHz, CDCl 3 ) δ 170.4, 136.6, 123.5, 60.4, 50.5, 20.5, 14.2. Spectroscopic data for H-NMR are in agreement with those reported ( 30 ).…”

Section: Methodssupporting

confidence: 89%

Clickable Vitamins as a New Tool to Track Vitamin A and Retinoic Acid in Immune Cells

et al. 2021

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“…Mesylation of compound 7 and subsequent treatment of the derivative obtained with magnesium bromide6 led to bromide 5 in high yield. The latter was transformed, in a moderate yield, into α‐methylene aldehyde 13 by Kornblum oxidation,21 and then into the diethyl acetal 14 by a standard procedure. Biohydrogenation of the methylene moiety in compound 14 with baker’s yeast led to chiral ( S )‐alcohol 3 , whose enantiomeric purity, as determined by Mosher’s method, was more than 97 % 22.…”

Section: Resultsmentioning

confidence: 99%

Transformation of Esters into 2‐Substituted Allyl Halides via Tertiary Cyclopropanols: Application in the Stereoselective Synthesis of (2S,3S,7S)‐3,7‐Dimethyl‐2‐pentadecyl Acetate, the Sex Pheromone of the Pine Sawfly Neodiprion sertifer

2006

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“…( E )-3-(5,5-Dimethyl-1,3-dioxan-2-yl)but-2-enal ( 6 ) [ 34 ]: To a stirred solution of acetal 4 (0.59 g, 1.93 mmol) in DMSO (10 mL), the following were added: K 2 HPO 4 (0.40 g, 2.28 mmol), KH 2 PO 4 (81 mg, 0.60 mmol), and NaI (29 mg, 0.19 mmol). The mixture was heated at 80 °C for 12 h and cooled to room temperature.…”

Section: Methodsmentioning

confidence: 99%

Oxo-Carotenoids as Efficient Superoxide Radical Scavengers

2022

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Oxo-carotenoids containing conjugated carbonyl groups in their chains were designed to be more efficient superoxide radical scavengers than natural carotenoids, β-carotene and canthaxanthin. A practical chain-extension method for polyene dials (e.g., crocetin dial) was also proposed based on Horner–Wadsworth–Emmons olefination. Double aldol condensation between polyene dials and acetophenones with ring substituents produced oxo-carotenoids with substituted benzene rings. The antioxidant activity of oxo-carotenoids was measured using DPPH (radical) and ABTS (cationic radical) scavenging assays and compared with the analysis with the superoxide (anionic radical) probe. An effective conjugation length by carbon–carbon double bonds is important to provide superior antioxidant activity for oxo-carotenoids, regardless of the type of radical probe used in the assay. Increasing electron density is favorable to strong antioxidant activity in DPPH, and the phenol group is favored in ABTS, whereas electron deficient oxo-carotenoids are very potent in the superoxide radical assay. All oxo-carotenoids exhibited 105~151% better superoxide radical scavenging activity compared to beta-carotene (100%), whereas 38~155% in DPPH and 16~96% in ABTS radical scavenging activities were observed.

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Facile synthesis of 4-acetoxy-2-methyl-2-butenal, a vitamin A precursor, from isoprene chlorohydrin

Cited by 22 publications

References 1 publication

Clickable Vitamins as a New Tool to Track Vitamin A and Retinoic Acid in Immune Cells

Clickable Vitamins as a New Tool to Track Vitamin A and Retinoic Acid in Immune Cells

Transformation of Esters into 2‐Substituted Allyl Halides via Tertiary Cyclopropanols: Application in the Stereoselective Synthesis of (2S,3S,7S)‐3,7‐Dimethyl‐2‐pentadecyl Acetate, the Sex Pheromone of the Pine Sawfly Neodiprion sertifer

Oxo-Carotenoids as Efficient Superoxide Radical Scavengers

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