Step-economy synthesis of beta-steryl sialosides using a sialyl iodide donor

Park Simon S.; Gervay-Hague Jacquelyn

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Step-economy synthesis of beta-steryl sialosides using a sialyl iodide donor

机译：使用SiaLyl碘化物供体的脂肪合成β-Steryl唾液酸

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Steryl glycosides are prevalent in nature and have unique biological activities dictated by sterol structure, sugar composition, and the stereochemical attachment of the aglycone. A single configurational switch can have profound biological consequences meriting the systematic study of structure and function relationships. Steryl congeners of N-acetyl neuraminic acid (NANA) impact neurobiological processes and may also mediate host/microbe interactions. In order to study these processes, a platform for the synthesis of beta-steryl sialosides has been established. Promoter-free glycosidations using a novel alpha-linked sialyl iodide donor efficiently provide unique amphiphilic sialoglycoconjugates for examining bioactivities in various systems.

机译：Steryl糖苷的自然界是普遍的，并且具有独特的生物活性，由甾醇结构，糖组合物和糖苷酮的立体化学附着决定。单个配置开关可以具有深刻的生物后果，可提供结构和功能关系的系统研究。 N-乙酰氨基酸（NANA）的STRYL CONGENS撞击神经生物学过程，也可以介导宿主/微生物相互作用。为了研究这些过程，已经建立了一种合成β-斯蒂尔氏菌皂苷的平台。使用新型α-连接的SiaLyl碘化物供体的启动子 - 无糖苷糖苷有效地提供独特的两亲性唾液甘学缀合物，用于检查各种系统中的生物活性。

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《The Journal of Antibiotics: An International Journal》 |2019年第6期|共12页
作者
Park Simon S.; Gervay-Hague Jacquelyn;
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Univ Calif Davis One Shields Ave Davis CA 95616 USA;

Univ Calif Davis One Shields Ave Davis CA 95616 USA;

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原文格式 PDF
正文语种 eng
中图分类药学;
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专利

1. Step-economy synthesis of beta-steryl sialosides using a sialyl iodide donor [J] . Park Simon S., Gervay-Hague Jacquelyn The Journal of Antibiotics: An International Journal . 2019,第6期

机译：使用SiaLyl碘化物供体的脂肪合成β-Steryl唾液酸
2. Highly Alpha-Selective Sialyl Phosphate Donors for Efficient Preparation of Natural Sialosides [J] . Che-Hsiung Hsu, Kuo-Ching Chu Dr., Yih-Shyan Lin, Chemistry - A European Journal . 2010,第6期

机译：高效制备天然唾液苷的高选择性α-唾液酸磷酸供体
3. An effective sialylation method using N-Troc- and N-Fmoc-protected beta-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen [J] . Adachi M., Tanaka H., Takahashi T. Synlett . 2004,第4期

机译：使用N-Troc和N-Fmoc保护的β-硫代苯基唾液酸的有效唾液酸化方法及其在一锅两步合成2,6-唾液酸T抗原中的应用
4. Chemoenzymatic Synthesis of Sialosides and TheirApplications [C] . Hai Yu, Harshal A. Chokhawala, Shengshu Huang, American Chemical Society . 2008

机译：化学酶合成唾液酸和缺陷
5. Synthesis of sialyl Lewis X mimetic as an inhibitor of E-selectin mediated cellular adhesion and a new method for the in situ generation of anhydrous hydrogen iodide in an organic solvent and its use in synthetic reactions. [D] . Chervin, Stephanie Marie. 2000

机译：唾液酸化的路易斯X模拟物作为E-选择蛋白介导的细胞粘附抑制剂的合成以及在有机溶剂中原位产生无水碘化氢的新方法及其在合成反应中的用途。
6. Synthesis and Intramolecular Glycosylation of Sialyl Mono-esters of o-Xylylene Glycol. The Importance of Donor Configuration and Nitrogen Protecting Groups on Cyclization Yield and Selectivity; Isolation and Characterization of a N-Sialyl Acetamide Indicative of Participation by Acetonitrile [O] . Harsha Amarasekara, David Crich -1

机译：邻二甲苯基乙二醇的唾液酸单酯的合成和分子内糖基化。供体构型和氮保护基对环化产率和选择性的重要性；指示乙腈参与的N-唾液酸乙酰胺的分离和表征
7. Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile [O] . Harsha Amarasekara, David Crich 2016

机译：邻二甲基二醇的SiaLyl单酯的合成与分子内糖基化。供体构型和氮保护组对环化产量和选择性的重要性;乙腈参与的N-SiAlyl乙酰胺的分离与表征

Step-economy synthesis of beta-steryl sialosides using a sialyl iodide donor

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