Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles.

Chiral 1,2,3-triazoles are highly attractive motifs in various fields. However, achieving catalytic asymmetric click reactions of azides and alkynes for chiral triazole synthesis remains a significant challenge, mainly due to the limited catalytic systems and substrate scope. Herein, we report an enantioselective azidation/click cascade reaction of N-propargyl-ß-ketoamides with a readily available and potent azido transfer reagent via copper catalysis, which affords a variety of chiral 1,2,3-triazoles with up to 99% yield and 95% ee under mild conditions. Notably, chiral 1,5-disubstituted triazoles that have not been accessed by previous asymmetric click reactions are also prepared with good functional group tolerance.

Azidobenziodazolones as Azido Sources for the Enantioselective Copper-Catalyzed Azidation of N-Unprotected 3-Trifluoromethylated Oxindoles.

Both azido (N3) and trifluoromethyl (CF3) groups are key moieties of numerous valuable molecules that are extensively applied in drug discovery, chemical biology, and synthetic chemistry. However, the asymmetric construction of chiral quaternary stereocenters bearing both N3 and CF3 groups is still unexplored. Herein, we report a kind of bench-stable and easily adjustable benziodazolone-based azidating reagents. These reagents were used to achieve an enantioselective copper-catalyzed azidation of N-unprotected 3-trifluoromethylated oxindoles to provide diverse enantioenriched 3-N3-3-CF3 oxindoles.

Alamandine protects against renal ischaemia-reperfusion injury in rats via inhibiting oxidative stress.

OBJECTIVE: This study was to determine whether alamandine (Ala) could reduce ischaemia and reperfusion (I/R) injury of kidney in rats. METHODS: Renal I/R was induced by an occlusion of bilateral renal arteries for 70 min and a 24-h reperfusion in vivo, and rat kidney proximal tubular epithelial cells NRK52E were exposed to 24 h of hypoxia and followed by 3-h reoxygenation (H/R) in vitro. RESULTS: The elevated serum creatinine (Cr), blood cystatin C (CysC) and blood urea nitrogen (BUN) levels in I/R rats were inhibited by Ala treatment. Tumour necrosis factor alpha (TNF)-α, IL-1ß, IL-6, cleaved caspase-3, cleaved caspase-8 and Bax were increased, and Bcl2 was reduced in the kidney of I/R rats, which were reversed by Ala administration. Ala reversed the increase of TNF-α, IL-1ß, IL-6, cleaved caspase-3, cleaved caspase-8 and Bax and the decrease of Bcl2 in the H/R NRK52E cells. Ala could also inhibit the increase of oxidative stress levels in the kidney of I/R rats. NADPH oxidase 1 (Nox1) overexpression reversed the improving effects of Ala on renal function, inflammation and apoptosis of I/R rats. CONCLUSION: These results indicated that Ala could improve renal function, attenuate inflammation and apoptosis in the kidney of I/R rats via inhibiting oxidative stress.

Genetic Diversity and Association Analysis for Solvent Retention Capacity in the Accessions Derived from Soft Wheat Ningmai 9.

Solvent retention capacity (SRC) test is an effective method for quality evaluation of soft wheat. Ningmai 9 is a founder in soft wheat breeding. The SRC and genotype of Ningmai 9 and its 117 derivatives were tested. Association mapping was employed to identify the quantitative trait loci (QTL) associated with SRCs. Ningmai 9 had the allele frequency of 75.60% and 67.81% to its first- and second-generation derivatives, respectively, indicating higher contribution than theoretical expectation. Neighbor-joining cluster based on the genotyping data showed that Ningmai 9 and most of its first-generation derivatives were clustered together, whereas its second-generation derivatives were found in another group. The variation coefficients of SRCs in the derivatives ranged from 5.35% to 8.63%. A total of 29 markers on 13 chromosomes of the genome were associated with the SRCs. There were 6 markers associated with more than one SRC or detected in two years. The results suggested that QTL controlling SRCs in Ningmai 9 might be different from other varieties. Markers Xgwm44, Xbarc126, Xwmc790, and Xgwm232 associated with SRCs in Ningmai 9 might be used for quality improvement in soft wheat breeding.

Genetic Contribution of Ningmai 9 Wheat to Its Derivatives Evaluated by Using SNP Markers.

Founder parent usually plays an important role in wheat breeding. Ningmai 9 is a soft wheat variety with good performance in yield, quality, and resistance to wheat disease. Therefore it serves as an important commercial variety and founder parent in middle and lower Yangtze River of China. To date, 20 new cultivars have been developed from Ningmai 9 and released to wheat production in the last 10 years. In this study, the 90K iSELECT ILLUMINA chip was used to analyze the genotype of Ningmai 9 and its 17 derivatives. The genetic similarity coefficients between Ningmai 9 and its derivatives were more than 0.7 except for Yangfumai 4. Neighbor-Joining analysis showed that Yangfumai 4 had the largest genetic distance from Ningmai 9 in all derivatives. There was a great difference for the same allele ratio in either derivatives or chromosomes, though the average values of the same allele ratio in genomes A, B, and D were close to each other. The phenotypic difference in Ningmai 9, Ningmai 13, and Yangfumai 4 was consistent with their difference in genetic background by comparing previous reported QTLs. Some hot chromosome regions were found and might be used for marker assisted selection in wheat breeding.

Genome-wide sequence characterization and expression analysis of major intrinsic proteins in soybean (Glycine max L.).

Water is essential for all living organisms. Aquaporin proteins are the major facilitator of water transport activity through cell membranes of plants including soybean. These proteins are diverse in plants and belong to a large major intrinsic (MIP) protein family. In higher plants, MIPs are classified into five subfamilies including plasma membrane intrinsic proteins (PIP), tonoplast intrinsic proteins (TIP), NOD26-like intrinsic proteins (NIP), small basic intrinsic proteins (SIP), and the recently discovered X intrinsic proteins (XIP). This paper reports genome wide assembly of soybean MIPs, their functional prediction and expression analysis. Using a bioinformatic homology search, 66 GmMIPs were identified in the soybean genome. Phylogenetic analysis of amino acid sequences of GmMIPs divided the large and highly similar multi-gene family into 5 subfamilies: GmPIPs, GmTIPs, GmNIPs, GmSIPs and GmXIPs. GmPIPs consisted of 22 genes and GmTIPs 23, which showed high sequence similarity within subfamilies. GmNIPs contained 13 and GmSIPs 6 members which were diverse. In addition, we also identified a two member GmXIP, a distinct 5(th) subfamily. GmMIPs were further classified into twelve subgroups based on substrate selectivity filter analysis. Expression analyses were performed for a selected set of GmMIPs using semi-quantitative reverse transcription (semi-RT-qPCR) and qPCR. Our results suggested that many GmMIPs have high sequence similarity but diverse roles as evidenced by analysis of sequences and their expression. It can be speculated that GmMIPs contains true aquaporins, glyceroporins, aquaglyceroporins and mixed transport facilitators.

Uncovering the salt response of soybean by unraveling its wild and cultivated functional genomes using tag sequencing.

Soil salinity has very adverse effects on growth and yield of crop plants. Several salt tolerant wild accessions and cultivars are reported in soybean. Functional genomes of salt tolerant Glycine soja and a salt sensitive genotype of Glycine max were investigated to understand the mechanism of salt tolerance in soybean. For this purpose, four libraries were constructed for Tag sequencing on Illumina platform. We identify around 490 salt responsive genes which included a number of transcription factors, signaling proteins, translation factors and structural genes like transporters, multidrug resistance proteins, antiporters, chaperons, aquaporins etc. The gene expression levels and ratio of up/down-regulated genes was greater in tolerant plants. Translation related genes remained stable or showed slightly higher expression in tolerant plants under salinity stress. Further analyses of sequenced data and the annotations for gene ontology and pathways indicated that soybean adapts to salt stress through ABA biosynthesis and regulation of translation and signal transduction of structural genes. Manipulation of these pathways may mitigate the effect of salt stress thus enhancing salt tolerance.

[Structures of transgenic integration loci in transformed plants].

The plants transformed by either Agrobacterium-mediated or directly delivered DNA transformation possess complex transgenic loci. The transgenes tend to be integrated into gene-rich regions on chromosomes due to selection of transgenic cells during tissue culture rather than integrated elsewhere randomly. Fragments of transferred DNA are interspersed with genomic DNA and filler DNA at most of transgenic loci except a few which contain complete single-copy of transgene. Analysis of transgenic loci flanking sequences indicated that deletion, duplication and chromosomal rearrangement often occurred for transgene and genomic DNA. The complete transgenic structure is important for its expression in transformed plants.

Deletion of a Chromosome Arm Altered Wheat Resistance to Fusarium Head Blight and Deoxynivalenol Accumulation in Chinese Spring.

Fusarium head blight (FHB), caused by Fusarium graminearum Schwabe, is an important disease of wheat worldwide. Production of deoxynivalenol (DON) in infected wheat grain by F. graminearum is a major safety concern when considering use of the grain as feed for livestock or for human consumption. Determining chromosome locations of FHB-related genes may facilitate enhancement of wheat resistance to FHB and DON accumulation. In this study, a set of 30 ditelosomic lines derived from Chinese Spring, a moderately FHB-resistant landrace from China, were evaluated for proportion of scabbed spikelets per inoculated spike in the greenhouse and for DON contamination in harvested grain over 2 years. Significant variation in the proportion of scabbed spikelets was observed among ditelosomic lines, ranging from 13 to 95%. Seven ditelosomic lines exhibited a greater proportion of scabbed spikelets and three of these also had greater DON content than Chinese Spring (P = 0.01), suggesting that those missing chromosome arms may carry genes that contribute to resistance to FHB. Six ditelosomic lines had a reduction in proportion of scabbed spikelets, suggesting that susceptibility factors or resistance suppressors may be on these missing chromosomal arms. Selection for low proportion of scabbed spikelets in general will select for low DON content.

[Analysis of major QTL for Fusarium head blight resistance on the short arm of chromosome 3B in wheat].

Three recombinant inbred populations, Ning894037/Alondra, Wangshuibai/Alondra and Sumai3/Alondra, were analyzed for QTLs associated with Fusarium head blight resistance by interval mapping and composite interval mapping in this study. The result showed that the major QTLs were detected on the short arm of chromosome 3B of all three resistant parents using the data of FHB resistance evaluated in greenhouse or field. They were located in the interval of 5.0 cM between BARC133 and Xgwm493 in Ning894037, 11.5 cM between BARC147 and Xgwm493 in Wangshuibai, and 13.0 cM between Xgwm533a and Xgwm493 in Sumai3, explaining 42.8%, 15.1% and 10.6% of the phenotypic variance for Type II resistance (spread within the spike), respectively. Some of the SSR markers linking to the major QTLs tightly can be used directly in marker-assisted breeding to improve FHB resistance in wheat.