Chiral Aryliodine-Catalyzed Asymmetric Oxidative C–N Bond Formation via Desymmetrization Strategy

An asymmetric oxidative C–N bond-forming reaction is developed using a chiral diiodospirobiindane derivative as the catalyst and <i>m</i>CPBA as a terminal oxidant. The protocol is based on an asymmetric desymmetrization strategy and affords lactams or spirolactams according to the different substituents on the substrates. The products are obtained in good yields and moderate to high enantioselectivities

A CuAAC/Ullmann C–C Coupling Tandem Reaction: Copper-Catalyzed Reactions of Organic Azides with <i>N</i>-(2-Iodoaryl)propiolamides or 2-Iodo-<i>N</i>-(prop-2-ynyl)benzenamines

A novel copper-catalyzed tandem reaction was developed by utilizing two famous copper-catalyzed reactions, CuAAC and Ullmann coupling. The trapping of the C–Cu intermediate produced in CuAAC led to further formation of an aryl C–C bond through intramolecular Ullmann C–C coupling

Demographic and clinical characteristics of the participants.

<p>Demographic and clinical characteristics of the participants.</p

Themes and subthemes of the study.

<p>Themes and subthemes of the study.</p

Effect of fatty acids on caveolin-1 subcellular location.

<p>CHO cells were cultured in Ham’s F-12 complete medium to 80% confluency. The cells were culture for 24 h with Ham’s F-12 containing 20% FBS, 1% BSA (fatty acid free), 1% BSA plus 200 µg/ml palmitic acid or 1% BSA plus 200 µg/ml stearic acid. The subcellular fractions were isolated with Opti-Prep method and subjected to Western blot using antibody against caveolin-1. The experiments were repeated two times and representative data are shown.</p

Quantification of fatty acids bound to caveolin-1, associated with caveolae, and present in CHO cells.

<p>The CHO cells were cultured in Ham’s F-12 medium to 90% confluency. Caveolae were isolated with Opti-Prep method and caveolin-1 was purified by immunoprecipitation. Total fatty acids were extracted from each sample with Folch reagent, methyl esterified with BF3, and then subjected to GC/MS equipped with Omegawax 250 capillary column. Fatty acids bound to caveolin-1 (A), associated with caveolae (B), and present in CHO cells (C) were quantified with FID. The experiments were repeated three times with triplicate measurements. Data are presented as Mean ± SD.</p

Separation of fatty acid methyl esters and determination of the sensitivity and linear range of GC/MS method.

<p>A mixture of standard fatty acid esters was subjected to GC/MS equipped with Omegawax 250 capillary column. Fatty acids were identified by mass spectrometer and quantified by FID. The measurement of fatty acid methyl esters with GC/MS was of high sensitivity, up to 40 pg of tricosanoic methyl ester, and had a wide linear range, up to 10 ng (inner figure, a and b).</p

Acylation of caveolin-1.

<p>CHO cells were cultured in Ham’s F-12 complete medium to 80% confluency. The cells were starved and then labeled with 2.5 mCi of ³H-palmitic acid or 25 µCi of ¹⁴C-stearic acid for 3 h at 37°C in the presence/absence of 30 times of non-labeled palmitic acid (C16∶0), stearic acid (C18∶0) or oleic acid (C18∶1). The cells were harvested in MBST/OG buffer and immunoprecipitated with anti-acveolin-1 IgG/protein A. The immunoprecipitated caveolin-1 was separated by SDS-PAGE, transferred to a membrane and the fatty acid associated with caveolin-1 was detected with autoradiogram. The experiments were repeated three times, and representative data are shown.</p