2011
DOI: 10.1002/ejic.201100605
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The Zinc‐Dependent Fluorescence of a Synthetic GFP‐Like Chromophore in Organic Solvents

Abstract: A synthetic green fluorescent protein analogue showed Zn 2+ -induced fluorescence in organic solvents (Φ = 0.07 at r.t. and up to 0.3 at low temperature). The experimental observations and theoretical calculations suggest that Zn 2+ binding inhibits the free rotation of an aryl-alkene bond, which allows

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Cited by 4 publications
(2 citation statements)
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“…Therefore, the hydroxyl group and amide needed to be protected by TBS and 2-(trimethylsilyl)ethoxymethyl (SEM) groups, respectively, to configure the desired enolate for the aldol reaction. The aldol reaction with 22 and imidazolyl aldehyde 23 proceeded smoothly to give 24a together with a minor diastereomer 24b ( a : b = 5.7:1), which could be separated by silica gel column chromatography. The elimination reaction of 24a under Sai’s conditions provided ( Z )-dehydrohistidine 25 as a single isomer in good yield.…”
mentioning
confidence: 99%
“…Therefore, the hydroxyl group and amide needed to be protected by TBS and 2-(trimethylsilyl)ethoxymethyl (SEM) groups, respectively, to configure the desired enolate for the aldol reaction. The aldol reaction with 22 and imidazolyl aldehyde 23 proceeded smoothly to give 24a together with a minor diastereomer 24b ( a : b = 5.7:1), which could be separated by silica gel column chromatography. The elimination reaction of 24a under Sai’s conditions provided ( Z )-dehydrohistidine 25 as a single isomer in good yield.…”
mentioning
confidence: 99%
“…Given that the HWE reaction strategy to construct the dehydrohistidine failed, we next attempted to introduce the imidazole moiety at the C12 position by the aldol reaction (Scheme ). The reaction of indoline 46 with N ‐Boc imidazolyl aldehyde 16 a 30a provided two aldol adducts, 48 a and 48 b , as diastereomers, plus an unexpected carbonated aldol adduct 49 , with yields of 50, 9, and 28 %, respectively. Carbonate 49 had the same stereochemistry as that of aldol adduct 48 a 31.…”
Section: Resultsmentioning
confidence: 99%