Enantioselective 6-<i>exo</i>-Bromoaminocyclization of Homoallylic <i>N</i>‑Tosylcarbamates Catalyzed by a Novel Monophosphine-Sc(OTf)₃ Complex

A highly enantioselective 6-<i>exo</i>-bromoaminocyclization of (<i>E</i>)-homoallylic <i>N</i>-tosylcarbamates catalyzed by a novel monophosphine-Sc­(OTf)₃ complex is described, giving a wide variety of optically active oxazinanones with high enantioselectivities

Phosphine Oxide–Sc(OTf)₃ Catalyzed Highly Regio- and Enantioselective Bromoaminocyclization of (<i>E</i>)‑Cinnamyl Tosylcarbamates. An Approach to a Class of Synthetically Versatile Functionalized Molecules

A highly regio- and enantioselective bromoaminocyclization of (<i>E</i>)-cinnamyl tosylcarbamates catalyzed by a chiral phosphine oxide–Sc­(OTf)₃ complex is described. A wide variety of optically active aryl 5-bromo-1,3-oxazinan-2-ones can be obtained with high yield and enantioselectivity

Synthesis of Optically Active Deuterated Primary Amines via Reduction of <i>N</i>-<i>tert</i>-Butanesulfinyl Aldimines

Optically active deuterated primary amines have been obtained with 78–98% ee’s from chiral <i>N</i>-<i>tert</i>-butanesulfinyl aldimines via reduction with <i>N</i>-Selectride and subsequent alcoholysis

Known sperm function associated genes affected by BPA.

<p>Known sperm function associated genes affected by BPA.</p

Summary of DhMR location distribution in sperm genome.

<p><b>a.</b> Atlas of DhMRs distribution in different chromosomes. Red lines in inner circle represent the position of hyper-hMRs and blue lines represent the position of hypo-hMRs. The length unit of the outer circle is 100Mb. <b>b</b>. DhMRs in gene body. <b>c.</b> 5hmc density in repeats. <b>d.</b> DhMRs affected repeats density.</p

Relationship of 5hmc, histone binding and expression of sperm genes.

<p><b>a.</b> relationship of H3K4me2 binding genes with DhMR genes and gene expression. <b>b.</b> relationship of H3K4me3 binding genes with DhMR genes and gene expression. <b>c.</b> relationship of H3K27me3 binding genes with DhMR genes and gene expression. <b>d.</b> relationship of H3K4me3/H3K27me3 binding genes with DhMR genes and gene expression.</p

5hmc distribution and BPA affection in promoter and gene body of sperm expressed or repressed genes.

<p><b>a</b>. Composition of 5hmc in promoter. <b>b</b>. Relative to control, the 5hmc level of each gene body in BPA-exposed sperm.</p

5hmc distribution in sperm genome.

<p><b>(a)</b>. 5hmc region ratio on the 19 autosomal chromosomes and the X and Y sex chromosomes. 100% cover ratio is defined as covering all the human genome. <b>(b)</b>. 5hmc increase ratio on the 19 autosomal chromosomes and the X and Y sex chromosomes, where hMeDIP-seq data covered genome size in each chromosome was defined as 1. <b>(c)</b> The ratio of 5hmc region in each gene body. 100% cover ratio is defined as covering all of the elements of a particular type in the human genome. <b>(d)</b> Proportion of 5hmC regions with different CpG densities. <b>(e)</b> Densities of 5hmC (counts per kilobases per million reads) in each 100bp regions with different CpG densities.</p

BPA raised 5hmc rate in sperm genes analyzed by qPCR.

<p><b>a.</b> Schematic representation of location of the CCGG loci in the 5UTR /promoters/ gene body of LINE-1, AChE, ATP2A1 and PPP2R3C, respectively. The red line indicates the region where enrichment of BPA-associated 5hmc was detected through high-throughput sequencing, and it is 200-bp long in LINE-1, AChE, ATP2A1, and 300-bp long in PPP2R3C, respectively. The green line represents the location of qPCR product. <b>b and d.</b> The 5hmc rates of four genes were measured using the pooled sperm samples from BPA-exposed men and the control men. The sperm DNA was treated with glucosylation followed by CCGG loci-dependent MspI/HpaII digestion (b), or was immuno-precipitated with the 5hmc antibody (d), and then used as the template of qPCR. The data were obtained from at least three independent experiments, and the values are shown as the mean ± SEM; * p< 0.05. <b>c.</b> The 5hmc rates were measured using individual samples. Five BPA-exposed samples and five control samples were randomly chosen for measurement of 5hmc rate. The values are shown as the mean ± SEM; * p< 0.05.</p

Known sperm function associated genes affected by BPA.

<p>Known sperm function associated genes affected by BPA.</p