Oleoscience
Online ISSN : 2187-3461
Print ISSN : 1345-8949
ISSN-L : 1345-8949
Efficient Total Synthesis of Mannosylerythritol Lipids (MELs) and Evaluation of Their Antibacterial Activity
Daisuke TAKAHASHIKazunobu TOSHIMA
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2020 Volume 20 Issue 5 Pages 209-214

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Abstract

Mannosylerythritol lipids (MELs) are glycolipid biosurfactants that show significant biochemical and physicochemical properties, such as antibacterial and surface activities. However, since heterogeneity always exists in MELs obtained from microbial products, especially with respect to the chain length of the fatty acids, chemically synthesized homogeneous and structurally well-defined MELs are required to elucidate the detailed structure-function relationships. Therefore, in this study, the total synthesis of the 20 homogeneous members of MEL-A-D (4 kinds) with different alkyl chain lengths (5 kinds) was effectively and systematically accomplished from our designed common key intermediate, which was stereoselectively synthesized by a recently developed our borinic-acid-catalyzed stereoselective β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated.

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© 2020 Japan Oil Chemists' Society
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