Four possible stereoisomers of 3-hydroxy-4-methyltetradecanoic acid were enantioselectively synthesized by using Sharpless epoxidation and a subsequent epoxide-ring opening reaction with trimethylaluminum as the key steps. The absolute configuration of the beta-oxyacid component of antifungal cyclodepsipeptides W493 A and B was consequently determined as 3S,4R.
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Solid-phase synthesis of carboxylic and oxamic acids via OsO4/NaIO4/HMTA-mediated oxidative cleavage of acetylenic peptides.
Org Lett
June 2007
Carlsberg Laboratory, SPOCC Centre, Gamle Carlsberg Vej 10, DK-2500 Valby, Denmark.
A general method for the solid-phase synthesis of carboxy-functionalized peptides by oxidative cleavage of alkynes is presented. Clean and quantitative conversion is enabled by the addition of bases, such as DABCO and HMTA, to the classical OsO4/NaIO4 mixture. The utility of the reaction is further illustrated by the synthesis of oxamic acids.
View Article and Find Full Text PDFEnantioselective synthesis of four isomers of 3-hydroxy-4-methyltetradecanoic acid, the constituent of antifungal cyclodepsipeptides W493 A and B.
Biosci Biotechnol Biochem
January 2005
Department of Biochemistry and Biotechnology, Faculty of Agriculture and Life Science, Hirosaki University, Hirosaki, Japan.
Four possible stereoisomers of 3-hydroxy-4-methyltetradecanoic acid were enantioselectively synthesized by using Sharpless epoxidation and a subsequent epoxide-ring opening reaction with trimethylaluminum as the key steps. The absolute configuration of the beta-oxyacid component of antifungal cyclodepsipeptides W493 A and B was consequently determined as 3S,4R.
View Article and Find Full Text PDFAntifungal Cyclodepsipeptides, W493 A and B, from Fusarium sp.: Isolation and Structural Determination.
Biosci Biotechnol Biochem
July 2016
a Department of Biochemistry and Biotechnology, Faculty of Agriculture and Life Science, Hirosaki University.
W493 A and B, which showed strong antifungal activity, were isolated from a culture broth of Fusarium sp. The structure of W493 B was determined to be that of a cyclodepsipeptide, cyclo(3S,4R-HMTA-D-allo-Thr-L-Ala-D-Ala-L-Gln-D-Tyr-L-Ile) (1) by MS and NMR data, an amino acid analysis, and synthesis of the component. HMTA represents 3-hydroxy-4-methyltetradecanoic acid.
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