Structure elucidation of glycosidic antibiotics, glykenins, from Basidiomycetes sp. II. Absolute structures of unusual polyhydroxylated C26-fatty acids, aglycones of glykenins
| Autor: | Yuji Mori, Vithaya Meevootisom, Sayuri Isobe, Suthum Intararuangsorn, Timothy W. Flegel, Makoto Suzuki, Yodhathai Thebtaranonth, Takeyuki Furuse, Naoko Rokkaku, Fumiko Nishida |
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| Rok vydání: | 1990 |
| Předmět: |
chemistry.chemical_classification
Chemical transformation Stereochemistry Enantioselective synthesis Absolute configuration Absolute (perfumery) Glycosidic bond General Chemistry General Medicine chemistry.chemical_compound Aglycone chemistry Drug Discovery Organic chemistry Aliphatic compound Octane |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 38:2381-2389 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.38.2381 |
| Popis: | The structures of three aglycones of glykenins, produced by Basidiomycetes sp., were determined to be (2S, 16R, 17S, 21R)-2, 16, 17, 21-, (2S, 17R, 18S, 22R)-2, 17, 18, 22-, and (2S, 17S, 18S, 22R)-2, 17, 18, 22-tetrahydroxyhexacosanoic acids (3a-c). The absolute configurations of two of the four hydroxy groups in 3a-c were established by chiral synthesis of the degradation products (6a-c and 7a-c). Chemical transformation of 3a-c to 6, 8-dioxabicyclo[3.2.1]octane derivatives (18-c) revealed the relative and absolute configurations of the acyclic 1, 2-diol moieties in 3a-c. |
| Databáze: | OpenAIRE |
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