16741-27-8Relevant articles and documents
Azidonitration of di-O-acetyl-L-fucal: X-Ray crystal structures of intermediate azidodeoxysugars and of the bacterial aminosugar N-acetyl-L-fucosamine
Alhassan, Abdul-Basit,McCutcheon, David C.,Zeller, Matthias,Norris, Peter
, p. 371 - 383 (2012)
The azidonitration of di-O-acetyl-L-fucal has previously been shown to be an efficient route to the bacterial aminosugar N-acetyl-L-fucosamine. Upon repeating this sequence, with updated versions of the glycal formation and amide installation steps, we have obtained X-ray crystal structures of several of the addition products, which are now reported along with the solid-state structure of N-acetyl-L-fucosamine itself. Copyright Taylor & Francis Group, LLC.
Excited-State Palladium-Catalyzed 1,2-Spin-Center Shift Enables Selective C-2 Reduction, Deuteration, and Iodination of Carbohydrates
Zhao, Gaoyuan,Yao, Wang,Mauro, Jaclyn N.,Ngai, Ming-Yu
supporting information, p. 1728 - 1734 (2021/02/06)
Excited-state catalysis, a process that involves one or more excited catalytic species, has emerged as a powerful tool in organic synthesis because it allows access to the excited-state reaction landscape for the discovery of novel chemical reactivity. Herein, we report the first excited-state palladium-catalyzed 1,2-spin-center shift reaction that enables site-selective functionalization of carbohydrates. The strategy features mild reaction conditions with high levels of regio- and stereoselectivity that tolerate a wide range of functional groups and complex molecular architectures. Mechanistic studies suggest a radical mechanism involving the formation of hybrid palladium species that undergoes a 1,2-spin-center shift followed by the reduction, deuteration, and iodination to afford functionalized 2-deoxy sugars. The new reactivity will provide a general approach for the rapid generation of natural and unnatural carbohydrates.
Alpha-L-fucosidase detection probe and preparation method and application thereof
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Paragraph 0038; 0042-0044, (2021/04/10)
The invention discloses an alpha-L-fucosidase detection probe. The structural general formula of the probe is shown in the specification, wherein in the formula I, R1 is an acetyl-protected monosaccharidyl or monosaccharidyl group; and R2 is a pyranonitrile group or a benzopyran nitrile group. The alpha-L-fucosidase detection probe prepared by the invention improves the detection sensitivity, can detect serum AFU with high selectivity, and can be used for kits or drugs for positioning and detecting cancer cells.
Neuroprotective activity of different monosaccharide-modified gastrodin analogs
Xu, Kun-Lun,Yu, Lan
, p. 1263 - 1269 (2020/01/21)
Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.