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Advances in carbohydrate chemistry and biochemistry最新文献

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Boron-mediated aglycon delivery (BMAD) for the stereoselective synthesis of 1,2-cis glycosides. 硼介导的糖苷传递(BMAD)用于立体选择性合成1,2-顺式糖苷。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.10.003
Daisuke Takahashi, Kazunobu Toshima
{"title":"Boron-mediated aglycon delivery (BMAD) for the stereoselective synthesis of 1,2-cis glycosides.","authors":"Daisuke Takahashi,&nbsp;Kazunobu Toshima","doi":"10.1016/bs.accb.2022.10.003","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.10.003","url":null,"abstract":"<p><p>1,2-cis Glycosides are frequently found in biologically active natural products, pharmaceutical compounds, and highly functional materials. Therefore, elucidating the role of mechanism of their biological activities will help clarify the structure-activity relationships of these diverse compounds and create new lead compounds for pharmaceuticals by modifying their structures. However, unlike 1,2-trans glycosides, the stereoselective synthesis of 1,2-cis glycosides remains difficult due to the nonavailability of neighboring group participation from the 2-O-acyl functionalities of the glycosyl donors. In this context, we recently developed organoboron-catalyzed 1,2-cis-stereoselecitve glycosylations, called boron-mediated aglycon delivery (BMAD) methods. In this review article, we introduce the BMAD methods and several examples of their application to the synthesis of biologically active glycosides.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"82 ","pages":"79-105"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9123353","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A bacterial glycolipid essential for membrane protein integration. 一种对膜蛋白整合必不可少的细菌糖脂。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.09.005
Kohki Fujikawa, Shoko Mori, Ken-Ichi Nishiyama, Keiko Shimamoto
{"title":"A bacterial glycolipid essential for membrane protein integration.","authors":"Kohki Fujikawa,&nbsp;Shoko Mori,&nbsp;Ken-Ichi Nishiyama,&nbsp;Keiko Shimamoto","doi":"10.1016/bs.accb.2022.09.005","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.09.005","url":null,"abstract":"<p><p>The proper conformation and orientation of membrane protein integration in cells is an important biological event. Interestingly, a new factor named MPIase (membrane protein integrase) was proven essential in this process in Escherichia coli, besides proteinaceous factors, such as Sec translocons and an insertase YidC. A combination of spectroscopic analyses and synthetic work has revealed that MPIase is a glycolipid despite its enzyme-like activity. MPIase has a long glycan chain comprised of repeating trisaccharide units, a pyrophosphate linker, and a diacylglycerol anchor. In order to determine the mechanism of its activity, we synthesized a trisaccharyl pyrophospholipid termed mini-MPIase-3, a minimal unit of MPIase, and its derivatives. A significant activity of mini-MPIase-3 indicated that it involves an essential structure for membrane protein integration. We also analyzed intermolecular interactions of MPIase or its synthetic analogs with a model substrate protein using physicochemical methods. The structure-activity relationship studies demonstrated that the glycan part of MPIase prevents the aggregation of substrate proteins, and the 6-O-acetyl group on glucosamine and the phosphate of MPIase play important roles for interactions with substrate proteins. MPIase serves at an initial step in the Sec-independent integration, whereas YidC, proton motive force, and/or SecYEG cooperatively function(s) with MPIase at the following step in vivo. Furthermore, depletion of the biosynthetic enzyme demonstrated that MPIase is crucial for membrane protein integration and cell growth. Thus, we elucidated new biological functions of glycolipids using a combination of synthetic chemistry, biochemistry, physicochemical measurements, and molecular-biological approaches.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"81 ","pages":"95-129"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10370674","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Therapeutic in vivo synthetic chemistry using an artificial metalloenzyme with glycosylated human serum albumin. 用糖基化人血清白蛋白的人工金属酶进行治疗性体内合成化学。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.10.001
Kenshiro Yamada, Kyohei Muguruma, Katsunori Tanaka
{"title":"Therapeutic in vivo synthetic chemistry using an artificial metalloenzyme with glycosylated human serum albumin.","authors":"Kenshiro Yamada,&nbsp;Kyohei Muguruma,&nbsp;Katsunori Tanaka","doi":"10.1016/bs.accb.2022.10.001","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.10.001","url":null,"abstract":"<p><p>The concept of \"therapeutic in vivo synthetic chemistry\" refers to chemical synthesis in living systems using new-to-nature reactions for the treatment or diagnosis of diseases. This review summarizes our development of therapeutic in vivo synthetic chemistry using glycan-modified human serum albumin (glycoHSA) and utilizing the selective glycan-targeting and metal protective effects of metal catalysts. The four artificial metalloenzymes with glycoHSA provided good cancer treatment results based on on-site drug synthesis and selective cell-tagging strategies. Thus, we propose that therapeutic in vivo synthetic chemistry using glycoHSA as a new modality of therapy or diagnosis is applicable to a wide range of diseases.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"82 ","pages":"11-34"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9123354","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of homogeneous glycoproteins with diverse N-glycans. 具有不同n -聚糖的均质糖蛋白的合成。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.09.004
Kota Nomura, Yanbo Liu, Yasuhiro Kajihara
{"title":"Synthesis of homogeneous glycoproteins with diverse N-glycans.","authors":"Kota Nomura,&nbsp;Yanbo Liu,&nbsp;Yasuhiro Kajihara","doi":"10.1016/bs.accb.2022.09.004","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.09.004","url":null,"abstract":"<p><p>In the post-genomic era, post- and co-translational modifications (P/C-TM) of proteins are known as the more essential elements for the activation of protein function. Among these protein modifications, glycosylation is one of the most abundant modifications in eukaryotic cells. The synthesis of glycoproteins with uniform glycan structures is essential for functional analysis of glycoproteins and biochemical research. For that purpose, chemical methods to synthesize glycoproteins with chemically uniform glycan structures have been developed. In this review, we highlight our recent advances in the preparation of homogeneous glycoproteins. Especially, we introduce both semi-synthesis and chemical synthesis of glycoproteins along with semi-synthesis of various complex-type N-glycans for the solid-phase synthesis of glycopeptide-thioesters.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"81 ","pages":"57-93"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10370672","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Hidetoshi Yamada: His journey in the carbohydrate world. 山田秀敏:他在碳水化合物世界的旅程。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.09.001
Yukishige Ito
{"title":"Hidetoshi Yamada: His journey in the carbohydrate world.","authors":"Yukishige Ito","doi":"10.1016/bs.accb.2022.09.001","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.09.001","url":null,"abstract":"<p><p>Professor Hidetoshi Yamada, who demonstrated his creativity in various respects, passed away in November 2019. His research targets were highly diverse, including sweet saponins, ellagitannins, novel cyclodextrins, and conformationally distorted donors for stereoselective glycosylations. In memory of his creativity, this chapter highlights his prominent achievements in carbohydrate chemistry.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"81 ","pages":"3-7"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10370671","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Conformationally restricted donors for stereoselective glycosylation. 立体选择性糖基化构象受限供体。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.10.005
Kaname Sasaki, Nanako Uesaki
{"title":"Conformationally restricted donors for stereoselective glycosylation.","authors":"Kaname Sasaki,&nbsp;Nanako Uesaki","doi":"10.1016/bs.accb.2022.10.005","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.10.005","url":null,"abstract":"<p><p>In nucleophilic reactions using sugars as electrophiles, i.e., glycosyl donors, their conformation affects the generation rate or stability of the glycosyl cation intermediates and determines at which side of the S<sub>N</sub>2-S<sub>N</sub>1 borderline and at what rate the reaction occurs. In addition, changes in the conformation create the steric or stereoelectronic effects of the substituents, which also change the reaction rate and stereoselectivity. Bulky silyl protecting groups, uronic acid esters, and transannular structures have been utilized to change the conformation. Consequently, reactions with unique reactivities and stereoselectivities have been developed. In this chapter, a discussion of the reaction mechanisms relating stereoselectivity to conformation is provided.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"82 ","pages":"107-155"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9123350","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Preface. 前言。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/S0065-2318(22)00032-4
David C Baker
{"title":"Preface.","authors":"David C Baker","doi":"10.1016/S0065-2318(22)00032-4","DOIUrl":"10.1016/S0065-2318(22)00032-4","url":null,"abstract":"","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":" ","pages":"ix-x"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35346637","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Yamada's carbohydrate chemistry. 山田碳水化合物化学。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.09.002
Shinnosuke Wakamori
{"title":"Yamada's carbohydrate chemistry.","authors":"Shinnosuke Wakamori","doi":"10.1016/bs.accb.2022.09.002","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.09.002","url":null,"abstract":"<p><p>This chapter describes the 21-year history of research conducted by Professor Hidetoshi Yamada. Sugars often exist in a six-membered ring structure, and the equatorial-rich chair conformation is stable. In contrast, its pyranose ring in a biological glycosylation is easily deformed and changed by various factors. Therefore, controlling the steric conformation of the pyranose ring is a great starting point to influence the stereoselectivity of the glycosylation reaction. His research developed stereoselective glycosylation reactions by deforming the sugar ring from the most stable equatorial-rich chair conformation. Initially, the research began to restrict the pyranose ring into the axial-rich chair form. The evolution to the locked skew-boat system allowed highly selective glycosylation by bulky silyl-protected or o-xylylene-bridged glycosyl donors. Development of the 1,1'-(ethane-1,2-diyl)dibenzene-2,2'-bis(methylene) bridging group created that which is known as the supple conformation system, which when combined with an α-selective glycosylation, led to the remarkable synthesis of the smallest cyclodextrins on record. Professor Yamada's consistent research in these areas willfully contributed to the development of carbohydrate chemistry.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"81 ","pages":"9-29"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10370670","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemical synthesis of sialoglyco-architectures. 唾液糖结构的化学合成。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.09.003
Hiromune Ando, Naoko Komura, Hide-Nori Tanaka, Akihiro Imamura, Hideharu Ishida
{"title":"Chemical synthesis of sialoglyco-architectures.","authors":"Hiromune Ando,&nbsp;Naoko Komura,&nbsp;Hide-Nori Tanaka,&nbsp;Akihiro Imamura,&nbsp;Hideharu Ishida","doi":"10.1016/bs.accb.2022.09.003","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.09.003","url":null,"abstract":"<p><p>The synthesis of sialic acid-containing molecules has posed a formidable challenge to carbohydrate chemists for over 50 years. Our research group has intensively searched for robust chemistry to enable the construction of a broad spectrum of sialic acid-containing molecules to advance the understanding and application of their biological functions. Herein, we describe our research findings on the development of sialic acid donors for α-selective glycosidation and the chemical synthesis of sialic acid- containing molecules, with a special focus on gangliosides and their fluorescent probes.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"81 ","pages":"31-56"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10370673","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Towards one-pot selective synthesis of cyclic oligosaccharides. 环低聚糖的一锅选择性合成。
2区 化学
Advances in carbohydrate chemistry and biochemistry Pub Date : 2022-01-01 DOI: 10.1016/bs.accb.2022.10.004
Toshiki Nokami
{"title":"Towards one-pot selective synthesis of cyclic oligosaccharides.","authors":"Toshiki Nokami","doi":"10.1016/bs.accb.2022.10.004","DOIUrl":"https://doi.org/10.1016/bs.accb.2022.10.004","url":null,"abstract":"<p><p>In this chapter are described electrochemical routes to cyclic oligosaccharides. While automated electrochemical methods have been used to prepare linear oligosaccharides, their conversion to cyclic oligosaccharides proved to be a complex process. The concept of polyglycosylation offers an interesting alternative, and the process which has been developed is that of a one-pot electrochemical polyglycosylation-isomerization-cyclization (ePIC) process.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"82 ","pages":"1-10"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9123347","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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