Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly

Kumpei Yano; Toshiyuki Itoh; Toshiki Nokami

doi:10.1016/j.carres.2020.108018

Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly

Carbohydr Res. 2020 Jun:492:108018. doi: 10.1016/j.carres.2020.108018. Epub 2020 Apr 18.

Authors

Kumpei Yano¹, Toshiyuki Itoh², Toshiki Nokami³

Affiliations

¹ Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552, Tottori, Japan.
² Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552, Tottori, Japan; Center for Research on Green Sustainable Chemistry, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552, Tottori, Japan.
³ Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552, Tottori, Japan; Center for Research on Green Sustainable Chemistry, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552, Tottori, Japan. Electronic address: tnokami@tottori-u.ac.jp.

PMID: 32339812
DOI: 10.1016/j.carres.2020.108018

Abstract

Total synthesis of Myc-IV(C16:0, S) via automated electrochemical assembly has been accomplished. This tetrasaccharide has been studied as a symbiotic signal molecule of Arbuscular Mycorrhiza fungi. We have achieved stereoselective synthesis of a disaccharide building block using the mixed-electrolyte system for electrochemical glycosylation; 2 + 1+1 strategy enables us to access the tetrasaccharide precursor and complete the synthesis Myc-IV(C16:0, S) efficiently.

MeSH terms

Automation*
Carbohydrate Conformation
Electrochemical Techniques*
Mycorrhizae / chemistry*