Synthesis of both enantiomers of lycoperdic acid, an unusual mushroom-derived amino acid
Autor: | Mikiko Kunisawa, Ryutaro Ishiuchi, Ryo Katsuta, Ken Ishigami, Tomoo Nukada, Arata Yajima |
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Rok vydání: | 2021 |
Předmět: |
Ketone
Stereochemistry Diol Chemistry Techniques Synthetic 010402 general chemistry 01 natural sciences Applied Microbiology and Biotechnology Biochemistry Analytical Chemistry Lactones chemistry.chemical_compound Amino Acids Molecular Biology chemistry.chemical_classification Bicyclic molecule biology 010405 organic chemistry Chemistry Organic Chemistry Lycoperdon perlatum Stereoisomerism General Medicine Glutamic acid biology.organism_classification 0104 chemical sciences Amino acid Dicarboxylic acid Enantiomer Agaricales Biotechnology |
Zdroj: | Bioscience, Biotechnology, and Biochemistry. 85:154-159 |
ISSN: | 1347-6947 |
DOI: | 10.1093/bbb/zbaa027 |
Popis: | An efficient synthesis of both enantiomers of lycoperdic acid, a 4-hydroxyglutamic acid derivative from edible mushroom Lycoperdon perlatum, was achieved from a chiral aminoalcohol. The key steps were a stereoselective introduction of a C3 unit into a bicyclic ketone and oxidative cleavage of a cyclic vicinal diol into a dicarboxylic acid. This report provides the first synthesis of (−)-lycoperdic acid. |
Databáze: | OpenAIRE |
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