This review summarizes our development of nitrogen-doped carbon-supported metal catalysts for precise organic synthesis, including asymmetric carbon-carbon bond forming reactions and electrochemical synthesis. These catalysts have been successfully applied to continuous-flow reactions. The nitrogen dopants critically activate and stabilize metal species, enabling unique reactivity and expanding the potential for novel organic reactions in heterogeneous manner.
{"title":"Development of Nitrogen-doped Carbon Supported Metal Catalysts for Green Organic Synthesis","authors":"Tomohiro Yasukawa","doi":"10.1093/bulcsj/uoae076","DOIUrl":"https://doi.org/10.1093/bulcsj/uoae076","url":null,"abstract":"This review summarizes our development of nitrogen-doped carbon-supported metal catalysts for precise organic synthesis, including asymmetric carbon-carbon bond forming reactions and electrochemical synthesis. These catalysts have been successfully applied to continuous-flow reactions. The nitrogen dopants critically activate and stabilize metal species, enabling unique reactivity and expanding the potential for novel organic reactions in heterogeneous manner.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"1 1","pages":""},"PeriodicalIF":4.0,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141613975","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Iezoside (1a) is a novel, potent sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitor from marine cyanobacterium. This paper describes the synthesis of comprehensive iezoside (1a) analogs containing C18/19 diastereomers, simplified analogs without the peptide unit, and aglycones. Evaluations of the antiproliferative activities against cancer cells and SERCA inhibitory activities of the synthesized analogs revealed how the absolute configurations at C18/19, peptide, and the sugar unit contribute to each bioactivity.Ca2+ ATPase (SERCA) inhibitor, Structure-activity relationship, Marine natural products
{"title":"Structure-Activity Relationship Studies on Iezoside, a Highly Potent Ca2+ ATPase Inhibitor","authors":"Naoaki Kurisawa, Kazuya Teranuma, Akari Noto, Arihiro Iwasaki, Yoshiki Kabashima, Rie Nakajima, Chikashi Toyoshima, Kiyotake Suenaga","doi":"10.1093/bulcsj/uoae070","DOIUrl":"https://doi.org/10.1093/bulcsj/uoae070","url":null,"abstract":"Iezoside (1a) is a novel, potent sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) inhibitor from marine cyanobacterium. This paper describes the synthesis of comprehensive iezoside (1a) analogs containing C18/19 diastereomers, simplified analogs without the peptide unit, and aglycones. Evaluations of the antiproliferative activities against cancer cells and SERCA inhibitory activities of the synthesized analogs revealed how the absolute configurations at C18/19, peptide, and the sugar unit contribute to each bioactivity.Ca2+ ATPase (SERCA) inhibitor, Structure-activity relationship, Marine natural products","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"64 1","pages":""},"PeriodicalIF":4.0,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141571535","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The present account reviews recent progress in the synthesis, functionalization, and application of discrete polyketones. Whereas most polyketones are synthesized as polydisperse polymers with various molecular chain lengths and sizes, discrete polyketones are obtained in chemically pure forms. This allows precise structural analysis using NMR and X-ray diffraction. Discrete polyketones have been used to determine the critical chain length that distinguishes the crystallization behaviors of small molecules from those of macromolecules. Calix[3]pyrrole, which is a ring-contracted analogue of porphyrinogen, was first obtained from a cyclic hexaketone. The discovery of the strain-induced ring expansion reaction of calix[3]pyrroles has provided an important insight into solving a long-standing enigma in porphyrin synthesis. Chemical derivatization of discrete polyketones using ketone-derived transformations has resulted in the generation of various functional molecules for potential applications. These molecules have been used to develop several materials, including luminescent chromophores, ion adsorbents, drug–drug conjugates, and microfluidic devices for cancer diagnosis.
本报告回顾了离散聚酮化合物在合成、功能化和应用方面的最新进展。大多数聚酮化合物是以分子链长度和大小各异的多分散聚合物形式合成的，而离散聚酮化合物则是以化学纯形式获得的。这样就可以利用核磁共振和 X 射线衍射进行精确的结构分析。离散多酮已被用于确定临界链长，以区分小分子和大分子的结晶行为。钙[3]吡咯是卟啉原的环收缩类似物，最早是从环状六酮中获得的。钙[3]吡咯的应变诱导扩环反应的发现，为解决卟啉合成中一个长期存在的谜团提供了重要的启示。利用酮衍生转化法对离散多酮进行化学衍生，产生了各种具有潜在应用价值的功能分子。这些分子已被用于开发多种材料，包括发光发色团、离子吸附剂、药物共轭物和用于癌症诊断的微流控装置。
{"title":"Discrete Polyketones: Synthesis, Derivatization, and Potential Applications","authors":"Yasuhide Inokuma","doi":"10.1093/bulcsj/uoae072","DOIUrl":"https://doi.org/10.1093/bulcsj/uoae072","url":null,"abstract":"The present account reviews recent progress in the synthesis, functionalization, and application of discrete polyketones. Whereas most polyketones are synthesized as polydisperse polymers with various molecular chain lengths and sizes, discrete polyketones are obtained in chemically pure forms. This allows precise structural analysis using NMR and X-ray diffraction. Discrete polyketones have been used to determine the critical chain length that distinguishes the crystallization behaviors of small molecules from those of macromolecules. Calix[3]pyrrole, which is a ring-contracted analogue of porphyrinogen, was first obtained from a cyclic hexaketone. The discovery of the strain-induced ring expansion reaction of calix[3]pyrroles has provided an important insight into solving a long-standing enigma in porphyrin synthesis. Chemical derivatization of discrete polyketones using ketone-derived transformations has resulted in the generation of various functional molecules for potential applications. These molecules have been used to develop several materials, including luminescent chromophores, ion adsorbents, drug–drug conjugates, and microfluidic devices for cancer diagnosis.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"14 1","pages":""},"PeriodicalIF":4.0,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141548439","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2024-01-27DOI: 10.1101/2023.06.21.545975
Joyce Liu, Daniel J Lustberg, Abigail Galvez, L Cameron Liles, Katharine E McCann, David Weinshenker
In rodents, exposure to predator odors such as cat urine acts as a severe stressor that engages innate defensive behaviors critical for survival in the wild. The neurotransmitters norepinephrine (NE) and dopamine (DA) modulate anxiety and predator odor responses, and we have shown previously that dopamine β-hydroxylase knockout (Dbh -/-), which reduces NE and increases DA in mouse noradrenergic neurons, disrupts innate behaviors in response to mild stressors such as novelty. We examined the consequences of Dbh knockout (Dbh -/-) on responses to predator odor (bobcat urine) and compared them to Dbh-competent littermate controls. Over the first 10 min of predator odor exposure, controls exhibited robust defensive burying behavior, whereas Dbh -/- mice showed high levels of grooming. Defensive burying was potently suppressed in controls by drugs that reduce NE transmission, while excessive grooming in Dbh -/- mice was blocked by DA receptor antagonism. In response to a cotton square scented with a novel "neutral" odor (lavender), most control mice shredded the material, built a nest, and fell asleep within 90 min. Dbh -/- mice failed to shred the lavender-scented nestlet, but still fell asleep. In contrast, controls sustained high levels of arousal throughout the predator odor test and did not build nests, while Dbh -/- mice were asleep by the 90-min time point, often in shredded bobcat urine-soaked nesting material. Compared with controls exposed to predator odor, Dbh -/- mice demonstrated decreased c-fos induction in the anterior cingulate cortex, lateral septum, periaqueductal gray, and bed nucleus of the stria terminalis, but increased c-fos in the locus coeruleus and medial amygdala. These data indicate that relative ratios of central NE and DA signaling coordinate the type and valence of responses to predator odor.
{"title":"Genetic disruption of dopamine β-hydroxylase dysregulates innate responses to predator odor in mice.","authors":"Joyce Liu, Daniel J Lustberg, Abigail Galvez, L Cameron Liles, Katharine E McCann, David Weinshenker","doi":"10.1101/2023.06.21.545975","DOIUrl":"10.1101/2023.06.21.545975","url":null,"abstract":"<p><p>In rodents, exposure to predator odors such as cat urine acts as a severe stressor that engages innate defensive behaviors critical for survival in the wild. The neurotransmitters norepinephrine (NE) and dopamine (DA) modulate anxiety and predator odor responses, and we have shown previously that dopamine β-hydroxylase knockout (<i>Dbh</i> -/-), which reduces NE and increases DA in mouse noradrenergic neurons, disrupts innate behaviors in response to mild stressors such as novelty. We examined the consequences of <i>Dbh</i> knockout (<i>Dbh</i> -/-) on responses to predator odor (bobcat urine) and compared them to Dbh-competent littermate controls. Over the first 10 min of predator odor exposure, controls exhibited robust defensive burying behavior, whereas <i>Dbh</i> -/- mice showed high levels of grooming. Defensive burying was potently suppressed in controls by drugs that reduce NE transmission, while excessive grooming in <i>Dbh</i> -/- mice was blocked by DA receptor antagonism. In response to a cotton square scented with a novel \"neutral\" odor (lavender), most control mice shredded the material, built a nest, and fell asleep within 90 min. <i>Dbh</i> -/- mice failed to shred the lavender-scented nestlet, but still fell asleep. In contrast, controls sustained high levels of arousal throughout the predator odor test and did not build nests, while <i>Dbh</i> -/- mice were asleep by the 90-min time point, often in shredded bobcat urine-soaked nesting material. Compared with controls exposed to predator odor, <i>Dbh</i> -/- mice demonstrated decreased c-fos induction in the anterior cingulate cortex, lateral septum, periaqueductal gray, and bed nucleus of the stria terminalis, but increased c-fos in the locus coeruleus and medial amygdala. These data indicate that relative ratios of central NE and DA signaling coordinate the type and valence of responses to predator odor.</p>","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"61 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10793432/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88774644","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Koki Sato, Enggah Kurniawan, Shun Sasaki, Kenta Matsusaka, Yasuhiro Yamada, Satoshi Sato
Silica-supported Cu (Cu/SiO2) prepared by an organic additive-assisted impregnation method was employed as catalysts for the dehydrogenation of 3-methyl-2-butanol (3M2BO) to 3-methyl-2-butanone (methyl isopropyl ketone, MIPK). The utilization of organic additives, especially mannitol, during the impregnation protocol, has led to the generation of a Cu/SiO2 catalyst containing highly dispersed Cu nanoparticles, i.e., high Cu surface area (SACu). These properties contributed to the high activity of the mannitol-assisted Cu/SiO2 catalyst, in which the activity was limited only by the equilibrium nature of the reaction. The proportional relation between the formation rate of MIPK with SACu confirmed the benefits of the utilization of organic additives. In addition, the improvement of SACu of Cu/SiO2 prepared with mannitol only gave a negligible side product originating from the dehydration of 3M2BO; thus, the equilibrium MIPK yield of 99.5% was achieved even at 300 °C.
{"title":"Vapor-phase Dehydrogenation of 3-Methyl-2-butanol over Silica-supported Cu Catalyst Prepared by Mannitol-assisted Impregnation","authors":"Koki Sato, Enggah Kurniawan, Shun Sasaki, Kenta Matsusaka, Yasuhiro Yamada, Satoshi Sato","doi":"10.1093/bulcsj/uoae001","DOIUrl":"https://doi.org/10.1093/bulcsj/uoae001","url":null,"abstract":"\u0000 Silica-supported Cu (Cu/SiO2) prepared by an organic additive-assisted impregnation method was employed as catalysts for the dehydrogenation of 3-methyl-2-butanol (3M2BO) to 3-methyl-2-butanone (methyl isopropyl ketone, MIPK). The utilization of organic additives, especially mannitol, during the impregnation protocol, has led to the generation of a Cu/SiO2 catalyst containing highly dispersed Cu nanoparticles, i.e., high Cu surface area (SACu). These properties contributed to the high activity of the mannitol-assisted Cu/SiO2 catalyst, in which the activity was limited only by the equilibrium nature of the reaction. The proportional relation between the formation rate of MIPK with SACu confirmed the benefits of the utilization of organic additives. In addition, the improvement of SACu of Cu/SiO2 prepared with mannitol only gave a negligible side product originating from the dehydration of 3M2BO; thus, the equilibrium MIPK yield of 99.5% was achieved even at 300 °C.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"73 21","pages":""},"PeriodicalIF":4.0,"publicationDate":"2024-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139440547","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tomoya Nakamura, Yoshio Kondo, Noboru Ohashi, Chihiro Sakamoto, Akio Hasegawa, Shuaifeng Hu, Minh Anh Truong, R. Murdey, Yoshihiko Kanemitsu, A. Wakamiya
Metal halide perovskite semiconductors are excellent materials for next-generation solar cells. As a result of research and development all over the world, the photoelectric conversion efficiency for single-cell devices has rapidly improved to over 26% (as of July 2023), while the record efficiency for silicon-on-perovskite tandem devices currently stands at 33.7% (reported in May 2023). Materials chemistry has made many important contributions toward these remarkable results. In this account, we will introduce our achievements in these areas of material chemistry research for improving the performance of perovskite photovoltaics, including the development of high-purity precursor materials, and precursor inks tailored for large-area printed perovskite films. Studies of the nucleation and crystallization process, including simulations, have led to the reliable fabrication of high-quality perovskite films. Diverse new charge collection materials, as well as compounds to effectively modify the perovskite surfaces, have improved solar cell performance.
{"title":"Materials Chemistry for Metal Halide Perovskite Photovoltaics","authors":"Tomoya Nakamura, Yoshio Kondo, Noboru Ohashi, Chihiro Sakamoto, Akio Hasegawa, Shuaifeng Hu, Minh Anh Truong, R. Murdey, Yoshihiko Kanemitsu, A. Wakamiya","doi":"10.1093/bulcsj/uoad025","DOIUrl":"https://doi.org/10.1093/bulcsj/uoad025","url":null,"abstract":"\u0000 Metal halide perovskite semiconductors are excellent materials for next-generation solar cells. As a result of research and development all over the world, the photoelectric conversion efficiency for single-cell devices has rapidly improved to over 26% (as of July 2023), while the record efficiency for silicon-on-perovskite tandem devices currently stands at 33.7% (reported in May 2023). Materials chemistry has made many important contributions toward these remarkable results. In this account, we will introduce our achievements in these areas of material chemistry research for improving the performance of perovskite photovoltaics, including the development of high-purity precursor materials, and precursor inks tailored for large-area printed perovskite films. Studies of the nucleation and crystallization process, including simulations, have led to the reliable fabrication of high-quality perovskite films. Diverse new charge collection materials, as well as compounds to effectively modify the perovskite surfaces, have improved solar cell performance.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"30 3","pages":""},"PeriodicalIF":4.0,"publicationDate":"2024-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139448649","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The magnetic orientation of iron oxide magnetic nanoparticles (MNPs) in the dried and aqueous dispersion samples was investigated under weak magnetic fields down to the geomagnetic field by the linear dichroism measurements. The geomagnetic orientation of MNPs was observed when the primary MNPs in dispersions made the agglomerates with a magnetic moment about ten times larger than that of the primary particle.
{"title":"Linear Dichroism Measurement of Geomagnetic Orientation of Magnetic Nanoparticles","authors":"Hitoshi Watarai","doi":"10.1093/bulcsj/uoad026","DOIUrl":"https://doi.org/10.1093/bulcsj/uoad026","url":null,"abstract":"\u0000 The magnetic orientation of iron oxide magnetic nanoparticles (MNPs) in the dried and aqueous dispersion samples was investigated under weak magnetic fields down to the geomagnetic field by the linear dichroism measurements. The geomagnetic orientation of MNPs was observed when the primary MNPs in dispersions made the agglomerates with a magnetic moment about ten times larger than that of the primary particle.","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"45 24","pages":""},"PeriodicalIF":4.0,"publicationDate":"2024-01-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139385021","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Bulletin of the Chemical Society of Japan, Volume 96, Issue 12, Page 1324-1330, December 2023.
《日本化学学会公报》，第96卷，第12期，1324-1330页，2023年12月。
{"title":"La(III)-Catalyzed Depolymerization of Poly(L-Lactic Acid) Yielding Chiral Lactates","authors":"Natsumi Kobayashi, Nobuyuki Komine, Kotohiro Nomura, Hiroshi Hirano, Masafumi Hirano","doi":"10.1246/bcsj.20230183","DOIUrl":"https://doi.org/10.1246/bcsj.20230183","url":null,"abstract":"Bulletin of the Chemical Society of Japan, Volume 96, Issue 12, Page 1324-1330, December 2023. <br/>","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"33 1","pages":""},"PeriodicalIF":4.0,"publicationDate":"2023-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138632284","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Bulletin of the Chemical Society of Japan, Volume 96, Issue 11, Page 1310-1315, November 2023.
日本化学学会公报，第96卷，第11期，第1310-1315页，2023年11月。
{"title":"Mechanistic Studies on Oxygen-Insertion into Osmium(III)–Carbon Bond via High-Valent Oxido-Osmium(V) Complex","authors":"Hideki Sugimoto, Kurumi Aoki, Shinobu Itoh","doi":"10.1246/bcsj.20230213","DOIUrl":"https://doi.org/10.1246/bcsj.20230213","url":null,"abstract":"Bulletin of the Chemical Society of Japan, Volume 96, Issue 11, Page 1310-1315, November 2023. <br/>","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"10 1","pages":""},"PeriodicalIF":4.0,"publicationDate":"2023-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138515505","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Bulletin of the Chemical Society of Japan, Volume 96, Issue 11, Page 1269-1273, November 2023.
日本化学学会公报，第96卷，第11期，1269-1273页，2023年11月。
{"title":"Structural and Magnetic Properties of the B-Site-Ordered Double Perovskites Ln2NiTiO6 (Ln = La, Pr, and Nd)","authors":"Masato Goto, Masato Okazaki, Yuichi Shimakawa","doi":"10.1246/bcsj.20230154","DOIUrl":"https://doi.org/10.1246/bcsj.20230154","url":null,"abstract":"Bulletin of the Chemical Society of Japan, Volume 96, Issue 11, Page 1269-1273, November 2023. <br/>","PeriodicalId":9511,"journal":{"name":"Bulletin of the Chemical Society of Japan","volume":"20 1","pages":""},"PeriodicalIF":4.0,"publicationDate":"2023-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138515482","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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