Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation
| Autor: | Mikiko Sodeoka, Yozo Okazaki, Eisuke Ota, Yuta Kuramoto, Masaki Morita, Go Hirai, Qianqian Wang, Kazuki Saito |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Glycosylation 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Total synthesis 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Glycolipid Membrane Drug Discovery lipids (amino acids peptides and proteins) Glucuronide Polyunsaturated fatty acid Diacylglycerol kinase |
| Zdroj: | Tetrahedron Letters. 58:2915-2918 |
| ISSN: | 0040-4039 |
| Popis: | We describe a total synthesis of a polyunsaturated fatty acid (PUFA)-containing glucuronosyldiacylglycerol (GlcADG), which is a surrogate glycolipid whose synthesis is remarkably upregulated in plant membranes under phosphorus-depleted conditions. Glycosylation between the glucuronide donor bearing 3,4-dimethoxybenzyl (DMPM) protecting groups and di-acylglycerol acceptor proceeded smoothly in the presence of gold(I) catalyst to provide the protected α-isomer of GlcADG as the major product. |
| Databáze: | OpenAIRE |
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