4.7 Review

Recent Advances in Organocatalytic Enantioselective Synthesis of Axially Chiral Allenes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 7, Pages 1212-1222

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200085

Keywords

Allene; Axial chirality; Enantioselectivity; Organocatalysis; Propargyl derivatives

Funding

  1. Shenzhen Innovation of Science and Technology Commission [20200925151614002]
  2. Natural Science Foundation of Shandong Province [ZR2021MB026]
  3. Special Funds of the Taishan Scholar Program of Shandong Province [tsqn201812047]
  4. Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]

Ask authors/readers for more resources

Axially chiral allenes are important natural products and synthetic molecules with significant biological activity. The catalytic enantioselective synthesis of these compounds has been widely studied, and many simple and efficient methods have been developed, thanks to the advancements in asymmetric organocatalysis.
Axially chiral allenes occur on a wide range of natural products and synthetic molecules with significant biological activity. Furthermore, they are versatile building blocks in organic synthesis because of their inherent chemical properties. Accordingly, catalytic enantioselective synthesis of axially chiral allenes has been paid much attention. Benefited from the development of asymmetric organocatalysis, many simple and efficient methods in terms of different catalytic systems as well as reaction partners have been developed. This review will focus on the recent progress in the field of organocatalytic enantioselective synthesis of allenes (2000-2022), which is organized according to types of allenes and the catalyst system used.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Microbiology

Paracoccus marinaquae sp. nov., isolated from coastal water of the Yellow Sea

Hua-Peng Xue, Zi-Yue Fu, Wei He, Lei Wang, Wen-Jun Li, Ai Hua Zhang, Jian-Ke Huang, Dao-Feng Zhang, Zhe Zhao

Summary: A new species of genus Paracoccus, named Paracoccus marinaquae sp. nov., was isolated from the coastal water of the Yellow Sea, China. This bacterium is Gram-stain-negative, non-motile and coccoid. It grows at a temperature range of 20-37 degrees C, pH range of 5.0-9.0, and NaCl concentration range of 0-7.0%. Based on phylogenetic analysis and phenotypic characteristics, it was determined to be a novel species within the genus Paracoccus.

ARCHIVES OF MICROBIOLOGY (2023)

Article Endocrinology & Metabolism

Longitudinal trends in glycated hemoglobin during and after tuberculosis treatment

Hardy Kornfeld, Elizabeth Procter-Gray, Satyavani Kumpatla, Kevin Kane, Wenjun Li, Matthew J. Magee, Subash Babu, Vijay Viswanathan

Summary: This study aimed to investigate the impact of pulmonary TB on glycemic status, as well as the associations of glycemic trends with antidiabetic therapy and TB outcomes. Data from two prospective cohort studies in Chennai, India were analyzed and it was found that baseline A1C levels decreased after TB treatment initiation in all groups. However, in patients with baseline diabetes, rising A1C levels during and after treatment were significantly associated with adverse TB outcomes.

DIABETES RESEARCH AND CLINICAL PRACTICE (2023)

Article Geochemistry & Geophysics

Natural Clinopyroxene Reference Materials for In Situ Microanalysis

Wenjun Li, Jing Wang, Mengmeng Cui, Xia Liu, Lihui Jia, Kaiyun Chen, Shitou Wu, Bingyu Gao, Dingshuai Xue, Yanhong Liu, Chao Li, Yang Luo, Benxun Su

Summary: Two clinopyroxene megacrysts, DMP-2 and DMP-3, from Cenozoic alkali basalts in Hannuoba region of China were characterized for major and trace element compositions through in situ microanalysis. Both clinopyroxene samples showed homogeneity in element mass fractions based on EPMA and LA-ICP-MS analyses. Bulk analyses using XRF, ICP-OES and solution ICP-MS techniques also revealed consistent major and trace element data. Thus, these samples can serve as potential reference materials for elemental in situ microanalysis, with recommended element mass fractions for thirty-two elements.

GEOSTANDARDS AND GEOANALYTICAL RESEARCH (2023)

Article Microbiology

Genomic Legacies of Ancient Adaptation Illuminate GC-Content Evolution in Bacteria

Wenkai Teng, Bin Liao, Mengyun Chen, Wensheng Shu

Summary: GC content is an important factor in microbial ecology and evolution, and the genomic GC of bacteria is characterized by heterogeneity between genomes, homogeneity within genomes, strong phylogenetic inertia, and association with the environment. Current hypotheses regarding direct selection or mutational biases cannot explain these features simultaneously. This study provides evidence that ancient adaptations have transformed the DNA replication and repair system, resulting in mutational biases that contribute to a bimodal distribution of genomic GC. This highlights the importance of indirect effects of natural selection in bacterial evolution.

MICROBIOLOGY SPECTRUM (2023)

Article Genetics & Heredity

Culturomics- and metagenomics-based insights into the microbial community and function of rhizosphere soils in Sinai desert farming systems

Wen-Hui Lian, Osama Abdalla Abdelshafy Mohamad, Lei Dong, Ling-Yu Zhang, Dong Wang, Lan Liu, Ming-Xian Han, Shuai Li, Shuang Wang, Andre Antunes, Bao-Zhu Fang, Jian-Yu Jiao, Wen-Jun Li

Summary: This study analyzed the microbial diversity and function of rhizosphere soil samples from Sinai Desert farming systems, revealing a wide range of microbial taxa and differences in composition between sampling sites. However, functional features were similar across different sites. The study highlights the importance of functional microbiomes in rhizosphere microbial communities.

ENVIRONMENTAL MICROBIOME (2023)

Article Plant Sciences

Comparative analysis of complete Artemisia subgenus Seriphidium (Asteraceae: Anthemideae) chloroplast genomes: insights into structural divergence and phylogenetic relationships

Guangzhao Jin, Wenjun Li, Feng Song, Lei Yang, Zhibin Wen, Ying Feng

Summary: This study sequenced and compared the chloroplast genomes of 16 species within the subgenus Seriphidium, revealing genetic consistency and variation in the subgenus. It also identified repetitive sequences and highly variable loci, and found inconsistencies between the molecular phylogeny and traditional taxonomy of subgenus Seriphidium. The whole chloroplast genomes can serve as molecular markers to infer interspecific relationships in this taxon.

BMC PLANT BIOLOGY (2023)

Article Microbiology

Salinibacterium sedimenticola sp. nov., Isolated from Tidal Flat Sediment

Chun-Yan Lu, Lei Dong, Shuai Li, Wen-Hui Lian, Zhi-Liang Lin, Zhuo-Huan Zheng, Lei Gao, Bao-Zhu Fang, Wen-Jun Li

Summary: A new actinobacterium, SYSU T00001(T), was isolated from a tidal flat sediment sample from Guangdong province, China. The isolate exhibited unique characteristics and showed highest similarity to Salinibacterium hongtaonis 194(T) based on phylogenetic analyses. Therefore, a novel species of the genus Salinibacterium, Salinibacterium sedimenticola sp. nov., is proposed, with SYSU T00001(T) as the type strain.

CURRENT MICROBIOLOGY (2023)

Article Fisheries

Characterization and expression analysis of the interferon regulatory factor (IRF) gene family in zig-zag eel (Mastacembelus armatus) against Aeromonas veronii infection

Chong Han, Wenwei Huang, Suhan Peng, Jiangwei Zhou, Huawei Zhan, Wenjun Li, Jian Gong, Qiang Li

Summary: In this study, 11 members of IRFs were identified and their expression patterns in different tissues were analyzed in the zig-zag eel. The results provide valuable information for understanding the antibacterial mechanism of IRFs in teleosts.

DEVELOPMENTAL AND COMPARATIVE IMMUNOLOGY (2023)

Article Microbiology

Sediment prokaryotic microbial community and potential biogeochemical cycle from saline lakes shaped by habitat

Yong-Hong Liu, Osama Abdalla Abdelshafy Mohamad, Lei Gao, Yuan-Guo Xie, Rashidin Abdugheni, Yin Huang, Li Li, Bao-Zhu Fang, Wen-Jun Li

Summary: This study investigated the distribution and potential functions of prokaryotes in different saline lakes in Xinjiang using the cultivation-independent method of amplicon sequencing. The results showed that Proteobacteria was the predominant community in all types of saline lakes, while Desulfobacterota, Firmicutes, Acidobacteriota, and Chloroflexi were mainly distributed in hypersaline, arid saline, and light saltwater lakes respectively. The functional group analysis revealed that fermentation was the main metabolic process of microbes in all saline lakes. Environmental factors such as SO42-, Na+, CO32-, and TN were found to significantly affect the microbial community.

MICROBIOLOGICAL RESEARCH (2023)

Article Biochemistry & Molecular Biology

The contrasting effects of fluctuating temperature on bacterial diversity and performances in temperate and subtropical soils

Xin-Feng Zhao, Bo-Hui Li, Wen-Sheng Shu, Yi-Qi Hao

Summary: This study found that fluctuating temperature has a positive effect on species diversity in soil bacterial communities compared to constant temperatures, and it also affects bacterial performances. The analysis showed that fluctuating temperature can delay species loss, and temperature-responsive species exhibit performance deviations under fluctuating temperature compared to constant temperatures. Additionally, the effects of fluctuating temperature on species diversity in soil bacterial communities may vary across latitude.

MOLECULAR ECOLOGY (2023)

Article Cell Biology

Panguiarchaeum symbiosum, a potential hyperthermophilic symbiont in the TACK superphylum

Yan-Ni Qu, Yang-Zhi Rao, Yan-Ling Qi, Yu-Xian Li, Andrew Li, Marike Palmer, Brian P. Hedlund, Wen-Sheng Shu, Paul N. Evans, Guo-Xing Nie, Zheng-Shuang Huo, Wen-Jun Li

Summary: By reconstructing 10 closely related metagenome-assembled genomes from hot spring habitats, we discovered a new species, Panguiarchaeum symbiosum. Our functional investigations revealed that Panguiarchaeum symbiosum is an anaerobic organism that exclusively grows in thermal habitats by fermenting peptides and producing sulfide and hydrogen. The species likely lives in a symbiotic lifestyle similar to DPANN archaea. Population metagenomics and metatranscriptomic analyses supported the proposed proteolytic catabolism and symbiotic lifestyle of Panguiarchaeum symbiosum. This study provides insights into the metabolism, evolution, and potential symbiotic lifestyle of this unique archaeon within the TACK superphylum.

CELL REPORTS (2023)

Article Microbiology

Monthly dynamics of microbial communities and variation of nitrogen-cycling genes in an industrial-scale expanded granular sludge bed reactor

Kun Zhang, Yanling Zhang, Maocheng Deng, Pengcheng Wang, Xiu Yue, Pandeng Wang, Wenjun Li

Summary: In this study, the dynamics of microbial and viral communities in an expanded granular sludge bed (EGSB) reactor were investigated. The results showed that COD, VSS/TSS ratio, and temperature were the main factors affecting the microbial community structure. The study also identified key genes involved in nitrogen cycling, with the dissimilatory nitrate reduction to ammonia (DNRA) and denitrification pathways dominating in the anaerobic system. The findings provide insights for the optimization of engineered systems.

FRONTIERS IN MICROBIOLOGY (2023)

Editorial Material Microbiology

Editorial: Thermophilic and halophilic extremophiles in Eurasian environments, volume II

Hongchen Jiang, Wen-Jun Li, Nils-Kare Birkeland, Dilfuza Egamberdieva

FRONTIERS IN MICROBIOLOGY (2023)

Article Pharmacology & Pharmacy

The impact of pharmacist early active consultation (PEAC) on multidrug resistance organism treatment outcomes: A prospective historically controlled study

Qian Du, Xin Xi, Jie Dong, Tongyan Zhang, Dongxuan Li, Yuzhu Dong, Wenjun Li, Guili Huang, Jun Zhu, Hailong Ran, Jinghui Gou, Cheng Chen, Zhanfeng Bai, Qinglong Liu, Wei Yao, Lei Zhang, Yutian Bi, Songqing Liu

Summary: This study found that early active pharmacy infectious disease consultation can reduce 30-day all-cause mortality and improve clinical outcomes in multidrug-resistant organism patients.

FRONTIERS IN PHARMACOLOGY (2023)

Article Microbiology

Hyperactive nanobacteria with host-dependent traits pervade Omnitrophota

Cale O. Seymour, Marike Palmer, Eric D. Becraft, Ramunas Stepanauskas, Ariel D. Friel, Frederik Schulz, Tanja Woyke, Emiley Eloe-Fadrosh, Dengxun Lai, Jian-Yu Jiao, Zheng-Shuang Hua, Lan Liu, Zheng-Han Lian, Wen-Jun Li, Maria Chuvochina, Brianna K. Finley, Benjamin J. Koch, Egbert Schwartz, Paul Dijkstra, Duane P. Moser, Bruce A. Hungate, Brian P. Hedlund

Summary: The candidate bacterial phylum Omnitrophota is poorly studied. By analyzing genomes and data from the Earth Microbiome Project, researchers found that Omnitrophota are ultra-small cells mainly found in water, sediments, and soils. These bacteria have reduced genomes but retain key metabolic pathways and symbiotic gene clusters, indicating a host-associated lifestyle. Additionally, stable-isotope probing identified certain Omnitrophota families as potential obligate bacterial predators. Overall, most Omnitrophota inhabit various ecosystems as predators or parasites.

NATURE MICROBIOLOGY (2023)

No Data Available