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DOI | 10.1126/science.aaw4866 |
Constrained sialic acid donors enable selective synthesis of alpha-glycosides | |
Komura, Naoko1; Kato, Keiichi2; Udagawa, Taro3; Asano, Sachi2,4; Tanaka, Hide-Nori1,4; Imamura, Akihiro2,4; Ishida, Hideharu1,2,4; Kiso, Makoto2,5; Ando, Hiromune1,4,5 | |
2019-05-17 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2019 |
卷号 | 364期号:6441页码:677-+ |
文章类型 | Article |
语种 | 英语 |
国家 | Japan |
英文摘要 | Sialic acid is a sugar residue present in many biologically significant glycans of mammals, commonly as a terminal alpha-glycoside. The chemical structure of sialic acid, which features an anomeric center with carboxyl and methylene substituents, poses a challenge for synthesis of the alpha-glycoside, thus impeding biological and therapeutic studies on sialic acid-containing glycans. We present a robust method for the selective alpha-glycosidation of sialic acid using macrobicyclized sialic acid donors as synthetic equivalents of structurally constrained oxocarbenium ions to impart stereoselectivity. We demonstrate the power of our method by showcasing broad substrate scope and applicability in the preparation of diverse sialic acid-containing architectures. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000468551000033 |
WOS关键词 | N-ACETYLNEURAMINIC ACID ; POTENTIAL-ENERGY SURFACES ; HYPERSPHERE SEARCH METHOD ; EFFICIENT SYNTHESIS ; STEREOSELECTIVE-SYNTHESIS ; NEURAMINIC ACID ; GLYCOSYLATION ; SIALYLATION ; DERIVATIVES ; ACETYL |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/201438 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Gifu Univ, Ctr Highly Adv Integrat Nano & Life Sci, Gifu 5011193, Japan; 2.Gifu Univ, Fac Appl Biol Sci, Dept Appl Bioorgan Chem, Gifu 5011193, Japan; 3.Gifu Univ, Fac Engn, Dept Chem & Biomol Sci, Gifu 5011193, Japan; 4.Gifu Univ, United Grad Sch Agr Sci, Gifu 5011193, Japan; 5.Kyoto Univ, Inst Integrated Cell Mat Sci, Kyoto 6068501, Japan |
推荐引用方式 GB/T 7714 | Komura, Naoko,Kato, Keiichi,Udagawa, Taro,et al. Constrained sialic acid donors enable selective synthesis of alpha-glycosides[J]. SCIENCE,2019,364(6441):677-+. |
APA | Komura, Naoko.,Kato, Keiichi.,Udagawa, Taro.,Asano, Sachi.,Tanaka, Hide-Nori.,...&Ando, Hiromune.(2019).Constrained sialic acid donors enable selective synthesis of alpha-glycosides.SCIENCE,364(6441),677-+. |
MLA | Komura, Naoko,et al."Constrained sialic acid donors enable selective synthesis of alpha-glycosides".SCIENCE 364.6441(2019):677-+. |
条目包含的文件 | 条目无相关文件。 |
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