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Synthesis of Immunopotent Alpha Glycolipids via Glycosyl Iodides

技术优势

Highly stereoselective and efficient Yields over 90% Exclusive formation of alpha glycolipids Beta glycolipids can also be synthesized in a stereoselective manner Does not require neighboring group participation, eliminates the numerous steps required for the installation and subsequent removal of protecting groups Mild reaction conditions which tolerate sensitive functionalities such as amides, esters and olefins

技术应用

Synthesis of libraries of alpha or beta-linked glycolipids Alpha glycolipids - study of NKT activation, the immune response pathway, and clinical application for disease treatment Beta glycolipids - study of cell-cell interactions as well as disease infection and progression.

详细技术说明

Alpha glycolipids have shown potent anti-tumor and anti-viral activities as well as potential for the treatment of certain autoimmune disorders via Natural Killer T (NKT) cell activation. Already in Phase I clinical trials for a variety of disease treatments that include cancer and diabetes, the structure of the glycolipid dictates the type as well as the extent of immunological activity. Beta-linked glycolipids play important roles in various biological processes via lipid rafts (highly ordered structural domains serve as anchoring platforms for extracellular proteins). While some beta-linked glycolipids are commercially available, they are typically obtained from bovine brains and are sold as mixtures with respect to the lipid component making definitive and reproducible results sometimes problematic. Current synthetic protocols afford either alpha/beta product mixtures, lack efficiency, or are limited by the reactivity of the reaction components. A readily accessible library of these alpha glycolipids is desirable for drug discovery and development while the stereoselective synthesis of pure beta-linked glycolipids is of great importance in understanding these and other biological processes. Researchers at the University of California, Davis have developed novel glycosyl iodide chemistry for the fast, efficient, and stereoselective syntheses of alpha and beta linked glycolipids. This technology utilizes glycosyl iodides as donors and involves subsequent reaction with fully functionalized lipid acceptors in a one-pot endeavor.

附加资料

Patent Number: US20130210752A1
Application Number: US13762400A
Inventor: HSIAO, Wendy Wen Luan | TAI, William Chi-Shing | JIANG, Zhi-Hong
Priority Date: 9 Feb 2012
Priority Number: US20130210752A1
Application Date: 8 Feb 2013
Publication Date: 15 Aug 2013
IPC Current: C12Q000126
US Class: 514026 | 435025 | 536005
Assignee Applicant: Hong Kong Baptist University
Title: USING A NOVEL HIGH-THROUGHPUT YEAST CELL-BASED SCREENING PLATFORM TO IDENTIFY HMG-COA REDUCTASE INHIBITORS FROM NATURAL PRODUCTS AND THE USES OF SUCH INHIBITORS THEREOF
Usefulness: USING A NOVEL HIGH-THROUGHPUT YEAST CELL-BASED SCREENING PLATFORM TO IDENTIFY HMG-COA REDUCTASE INHIBITORS FROM NATURAL PRODUCTS AND THE USES OF SUCH INHIBITORS THEREOF
Summary: For screening to identify enzyme 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMG-CoAR) inhibitors; in composition for treating/preventing a disease, condition associated with elevated cholesterol and/or blood lipid level (selected from hypercholesterolemia or hyperlipidemic) (all claimed).
Novelty: Screening to identify enzyme 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors involves measuring cell viability of yeast strain containing 3-hydroxy-3-methylglutaryl 1 overexpression plasmid, contacting and adding mevalonate