Iron-Catalyzed Photoredox Intermolecular Dearomatization of Benzothiazoles with Alkanes

Benzothiazolines, with their versatile nature, serve as fundamental building blocks for the synthesis of significant biological compounds. However, methods for the preparation of benzothiazolines from readily available starting materials are limited. An efficient synthesis of benzothiazoline via photoredox-catalyzed dearomatization of benzothiazole derivatives has been achieved at room temperature. This catalysis proceeds via a ligand to metal charge transfer process, and FeCl3 plays a dual role as an indirect HAT reagent and reducing agent. This methodology can be conveniently scaled up, and most of the alkylated products can be purified without chromatography. In addition, this process exhibited the advantages of low cost, high reaction efficiency, and mild conditions

Construction of PSLIN.

<p>A network in the left represents a global PIN. A eukaryotic cell in the center can be divided into 11 compartments, <i>Endoplasmic</i>, <i>Cytoskeleton</i>, <i>Golgi</i>, <i>Cytosol</i>, <i>Lysosome</i>(or <i>Vacuole</i>), <i>Mitochondrion</i>, <i>Endosome</i>, <i>Plasma</i>, <i>Nucleus</i>, <i>Peroxisome</i> and <i>Extracellular</i>, where <i>Lysosome</i> only exists in animal cells. For each compartment, a PSLIN of this compartment is constituted by the proteins localized in this compartment and their interactions. With the subcellular localization information of proteins, the PSLINs can be generated by mapping the global PIN to each compartment separately.</p

The schematic of LSED method.

<p>The schematic of LSED method.</p

Percentage of top <i>c</i>% ranked proteins, identified by LSED-XC methods and XC methods, to be essential proteins of <i>Saccharomyces cerevisiae</i>.

<p>Eight centrality methods (DC, BC, CC, SC, EC, IC, NC, and ION) were adopted to calculate centrality scores from the global PIN, respectively. LSED was combined with these centrality methods to calculate Localization-specific Centrality Scores from PSLINs separately. In (a)-(f), all the centrality methods are denoted as XC in the legend, and LSED with different XC methods are denoted as LSED-XC in the legend. The proteins are ranked in the descending order based on their Localization-specific Centrality Scores (<i>LCSs</i>) and centrality scores computed by LSED-XC methods and XC methods, respectively. Then, top 1%, 5%, 10%, 15%, 20% and 25% of the ranked proteins are selected as candidates for essential proteins. According to the list of known essential proteins, the percentages of true essential proteins were calculated. The figure shows the percentage of true essential proteins identified by each method in each top percentage of ranked proteins. The digits in brackets stand for the number of proteins ranked in each top percentage. For example, since the total number of ranked proteins of <i>Saccharomyces cerevisiae</i> is 6,304, the number of proteins ranked in top 1% is about 63 (= 6,304*1%).</p

Percentage of top <i>c</i>% ranked proteins, identified by LSED-XC methods and XC methods, to be essential proteins of <i>Homo sapiens</i>.

<p>Eight centrality methods (DC, BC, CC, SC, EC, IC, NC, and ION) were adopted to calculate centrality scores from the global PIN, respectively. LSED was combined with these centrality methods to calculate Localization-specific Centrality Scores from PSLINs separately. In (a)-(f), all the centrality methods are denoted as XC in the legend, and LSED with different XC methods are denoted as LSED-XC in the legend. The proteins are ranked in the descending order based on their Localization-specific Centrality Scores (<i>LCSs</i>) and centrality scores computed by LSED-XC methods and XC methods, respectively. Then, top 1%, 5%, 10%, 15%, 20% and 25% of the ranked proteins are selected as candidates for essential proteins. According to the list of known essential proteins, the percentages of true essential proteins were calculated. The figure shows the percentage of true essential proteins identified by each method in each top percentage of ranked proteins. The digits in brackets stand for the number of proteins ranked in each top percentage. For example, the total number of ranked proteins of Homo sapiens is 16,275, thus the number of proteins ranked in top 1% is about 162 (= 16,275*1%).</p

Percentage of top <i>c</i>% ranked proteins, identified by LSED-XC methods and XC methods, to be essential proteins of <i>Mus musculus</i>.

<p>Eight centrality methods (DC, BC, CC, SC, EC, IC, NC, and ION) were adopted to calculate centrality scores from the global PIN, respectively. LSED was combined with these centrality methods to calculate Localization-specific Centrality Scores from PSLINs separately. In (a)-(f), all the centrality methods are denoted as XC in the legend, and LSED with different XC methods are denoted as LSED-XC in the legend. The proteins are ranked in the descending order based on their Localization-specific Centrality Scores (<i>LCSs</i>) and centrality scores computed by LSED-XC methods and XC methods, respectively. Then, top 1%, 5%, 10%, 15%, 20% and 25% of the ranked proteins are selected as candidates for essential proteins. According to the list of known essential proteins, the percentages of true essential proteins were calculated. The figure shows the percentage of true essential proteins identified by each method in each top percentage of ranked proteins. The digits in brackets stand for the number of proteins ranked in each top percentage. For example, the total number of ranked proteins of <i>Mus musculus</i> is 6,582, thus the number of proteins ranked in top 1% is about 65 (= 6,582 *1%).</p

Statistics of proteins, PPIs, essential proteins, and proteins annotated by 11 labeled compartments in the global PIN of each species.

<p>#Protein, #PPI, #<i>Essential protein</i>, and #<i>Annoted Protein</i> denote the numbers of proteins, PPIs, essential proteins and proteins annotated by 11 labeled compartments in the global PIN of each species, respectively.</p><p>Statistics of proteins, PPIs, essential proteins, and proteins annotated by 11 labeled compartments in the global PIN of each species.</p

Percentage of top <i>c</i>% ranked proteins, identified by LSED-XC methods and XC methods, to be essential proteins of <i>Drosophila melanogaster</i>.

<p>Eight centrality methods (DC, BC, CC, SC, EC, IC, NC, and ION) were adopted to calculate centrality scores from the global PIN, respectively. LSED was combined with these centrality methods to calculate Localization-specific Centrality Scores from PSLINs separately. In (a)-(f), all the centrality methods are denoted as XC in the legend, and LSED with different XC methods are denoted as LSED-XC in the legend. The proteins are ranked in the descending order based on their Localization-specific Centrality Scores (<i>LCSs</i>) and centrality scores computed by LSED-XC methods and XC methods, respectively. Then, top 1%, 5%, 10%, 15%, 20% and 25% of the ranked proteins are selected as candidates for essential proteins. According to the list of known essential proteins, the percentages of true essential proteins were calculated. The figure shows the percentage of true essential proteins identified by each method in each top percentage of ranked proteins. The digits in brackets stand for the number of proteins ranked in each top percentage. For example, the total number of ranked proteins of <i>Drosophila melanogaster</i> is 8,020, thus the number of proteins ranked in top 1% is about 80 (= 8,020 *1%).</p

The <i>AKAcc</i>s of each method in different top percentages of ranked proteins over four species.

<p>Four species are <i>Saccharomyces cerevisiae</i>, <i>Homo sapiens</i>, <i>Mus musculus</i> and <i>Drosophila melanogaster</i>. When top 1%, 5%, 10%, 15%, 20% and 25% of the ranked proteins are selected as candidates for essential proteins, according to the list of known essential proteins of each species, the <i>Acc</i> of each method in each top percentage of ranked proteins was calculated. (a)-(f) illustrate the <i>AKAcc</i>s of LSED-XC methods and XC methods in the top 1%, 5%, 10%, 15%, 20%, and 25% of ranked proteins over four species, respectively. In (a)-(f), all the centrality methods are denoted as XC in the legend, and LSED with different XC methods are denoted as LSED-XC in the legend.</p

Percentage of different proteins, resulted by LSED-XC methods and the corresponding XC methods, to be essential proteins.

<p>Different proteins between two prediction methods are the proteins predicted by one method while neglected by the other method. (a)-(d) illustrate the percentages of true essential proteins in the different proteins from the top 100 protein sets ranked by LSED-XC methods and XC methods for <i>Saccharomyces cerevisiae</i>, <i>Homo sapiens</i>, <i>Mus musculus</i> and <i>Drosophila melanogaster</i>, respectively. In (a)-(d), the X axis represents the number of different proteins between LSED-XC and XC, and the Y axis represents the percentage of true essential proteins in the different proteins. In (a)-(d), all the centrality methods are denoted as XC in the legend, and LSED with different XC methods are denoted as LSED-XC in the legend.</p