Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity

Junki Nashida; Nobuya Nishi; Yoshiaki Takahashi; Chigusa Hayashi; Masayuki Igarashi; Daisuke Takahashi; Kazunobu Toshima

doi:10.1021/acs.joc.8b00032

Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity

Junki Nashida, Nobuya Nishi, Yoshiaki Takahashi, Chigusa Hayashi, Masayuki Igarashi, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

Abstract

The total synthesis of the 20 homogeneous members of mannosylerythritol lipids (MELs) with different alkyl chain lengths was effectively and systematically accomplished from a strategically designed common key intermediate that was stereoselectively constructed by the borinic acid catalyzed β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated. Our results demonstrated that not only the length of the alkyl chains but also the pattern of Ac groups on the mannose moiety were important factors for antibacterial activity.

Original language	English
Pages (from-to)	7281-7289
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	83
Issue number	13
DOIs	https://doi.org/10.1021/acs.joc.8b00032
Publication status	Published - 2018 Jul 6

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.8b00032

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title = "Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity",

abstract = "The total synthesis of the 20 homogeneous members of mannosylerythritol lipids (MELs) with different alkyl chain lengths was effectively and systematically accomplished from a strategically designed common key intermediate that was stereoselectively constructed by the borinic acid catalyzed β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated. Our results demonstrated that not only the length of the alkyl chains but also the pattern of Ac groups on the mannose moiety were important factors for antibacterial activity.",

author = "Junki Nashida and Nobuya Nishi and Yoshiaki Takahashi and Chigusa Hayashi and Masayuki Igarashi and Daisuke Takahashi and Kazunobu Toshima",

note = "Funding Information: This research was supported in part by the JSPS KAKENHI grant numbers JP16H01161 in Middle Molecular Strategy and JP16K05781 in Scientific Research (C), SUNBOR Grant from the Suntory Foundation for Life Sciences,and TOBE MAKI Scholarship Foundation. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.joc.8b00032",

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T1 - Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity

AU - Nashida, Junki

AU - Nishi, Nobuya

AU - Takahashi, Yoshiaki

AU - Hayashi, Chigusa

AU - Igarashi, Masayuki

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by the JSPS KAKENHI grant numbers JP16H01161 in Middle Molecular Strategy and JP16K05781 in Scientific Research (C), SUNBOR Grant from the Suntory Foundation for Life Sciences,and TOBE MAKI Scholarship Foundation. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/7/6

Y1 - 2018/7/6

N2 - The total synthesis of the 20 homogeneous members of mannosylerythritol lipids (MELs) with different alkyl chain lengths was effectively and systematically accomplished from a strategically designed common key intermediate that was stereoselectively constructed by the borinic acid catalyzed β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated. Our results demonstrated that not only the length of the alkyl chains but also the pattern of Ac groups on the mannose moiety were important factors for antibacterial activity.

AB - The total synthesis of the 20 homogeneous members of mannosylerythritol lipids (MELs) with different alkyl chain lengths was effectively and systematically accomplished from a strategically designed common key intermediate that was stereoselectively constructed by the borinic acid catalyzed β-mannosylation reaction. In addition, their antibacterial activities against Gram-positive bacteria were evaluated. Our results demonstrated that not only the length of the alkyl chains but also the pattern of Ac groups on the mannose moiety were important factors for antibacterial activity.

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Systematic and Stereoselective Total Synthesis of Mannosylerythritol Lipids and Evaluation of Their Antibacterial Activity

Abstract

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