Synthesis of four n-alkanes with terminal dipolar substituents

Ainscow, T.A.; Belmont, M.R.; Henshall, J. L.; Hooper, Robert; Simmonds, Derek J.

doi:10.1016/s0040-4020(01)89937-3

Cited by 13 publications

(5 citation statements)

References 25 publications

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“…The synthesis of Di-12A-ASPBS (4-{(E)-2-[4-(bis-w-hydroxydodecylamino)phenyl]vinyl}-1-(4-sulfonatobutyl)pyridinium; 3) was performed analogously to the synthesis of Di-4-ASPBS, with modifications (Scheme 1). [21] 1-(Bis-12-hydroxydodecylamino)-4-bromobenzene (1): In the first step, p-bromoaniline was alkylated with 12-iodododecan-1-ol (2.5 mol equiv, typically 200 mmol, obtained from 12-bromododecan-1-ol [39] ) in DMF containing K 2 CO 3 (2.5 mol equiv, 120 8C, 48 h). The cooled solution was then distributed between EtOAc and water.…”

Section: Methodsmentioning

confidence: 99%

Genetic Targeting of Individual Cells with a Voltage‐Sensitive Dye through Enzymatic Activation of Membrane Binding

2006

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Optical recording of the electrical activity of individual neurons in culture or in a tissue requires cell-selective staining with a fluorescent voltage-sensitive dye. In a proof-of-principle experiment, we implement a novel approach to genetically targeted staining. The method relies on a water-soluble precursor dye and an overexpressed cell-surface enzyme that transforms the precursor into a hydrophobic dye that binds to the targeted cell. We fused an alkaline phosphatase to a specifically designed general-purpose membrane anchor, and the fusion protein was expressed on the surface of HEK293 cells, as was corroborated by immuno- and histochemical staining. We next synthesised an amphiphilic hemicyanine dye containing two enzymatically cleavable phosphate groups at its hydrocarbon tails. When the phosphate groups were removed, the binding to membranes was enhanced by a factor of a thousand, as shown by titration with lipid vesicles. We observed selective staining of enzymatically active cells by fluorescence microscopy in a mixed population of phosphatase-transfected and untransfected HEK293 cells. The critical parameters of enzyme-induced cell-selective staining were elucidated by a simple kinetic model to guide further developments of the method.

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Section: Methodsmentioning

confidence: 99%

Genetic Targeting of Individual Cells with a Voltage‐Sensitive Dye through Enzymatic Activation of Membrane Binding

2006

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“…Diiodide 14 was also prepared by Ainscow and co-workers from cyclododecanone through 5 steps. 15 Our synthetic procedure was much more efficient than that of the reported. …”

Section: Scheme 1 Synthesis Of (R)-akolactone B (1a)mentioning

confidence: 79%

Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide

Hikosaka

Hattori

Makabe

2014

Tetrahedron: Asymmetry

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“…Using the same procedure, Ainscow et al . reported a high‐yield preparation of long‐chain ω‐functionalized nitroalkanes 11 (Table ).…”

Section: Preparation Of Nitroalkanes By Displacement Processesmentioning

confidence: 99%

Synthetic Procedures for the Preparation of Nitroalkanes

Ballini

Palmieri

2018

Adv Synth Catal

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Nitroalkanes, mainly the primary ones, are the keys tarting materials for the synthesis of al arge variety of important targets.H owever, in spite of their strategic synthetic importance,e very single type of nitroalkane ande very single procedure are relegated to individual contributions.T hus,t his review represents the first exhaustive collectiono f procedures for their synthesisa nd,c onsequently,i t can be considereda savery important tool for a growing use of nitroalkanes as key synthetic building blocks. Scheme 18. b-Keto-w-nitrotrimethylsilanes 60. Scheme19. Preparation of 61 b-nitrocycloalkanols. Scheme20. Synthesis of ketonitroalkanes 62. Scheme 34. Conversion of b-nitrostyrenes into a-nitro acetophenones. Scheme 35. Conversion of olefins into a-nitro ketones. Scheme36. Synthesis of b-nitro carbonyl compounds. Scheme37. Protection of 3-nitropropanal.

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Synthesis of four n-alkanes with terminal dipolar substituents

Cited by 13 publications

References 25 publications

Genetic Targeting of Individual Cells with a Voltage‐Sensitive Dye through Enzymatic Activation of Membrane Binding

Genetic Targeting of Individual Cells with a Voltage‐Sensitive Dye through Enzymatic Activation of Membrane Binding

Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide

Synthetic Procedures for the Preparation of Nitroalkanes

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