Solid-Phase Total Synthesis of Sandramycin and Its Analogues

Yuya Komatani; Kyoka Momosaki; Akira Katsuyama; Kazuki Yamamoto; Rintaro Kaguchi; Satoshi Ichikawa

doi:10.1021/acs.orglett.2c04327

Solid-Phase Total Synthesis of Sandramycin and Its Analogues

Org Lett. 2023 Jan 27;25(3):543-548. doi: 10.1021/acs.orglett.2c04327. Epub 2023 Jan 18.

Authors

Yuya Komatani¹, Kyoka Momosaki¹, Akira Katsuyama^{1

2}, Kazuki Yamamoto^{1

3}, Rintaro Kaguchi¹, Satoshi Ichikawa^{1

2}

Affiliations

¹ Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
² Global Station for Biosurfaces and Drug Discovery, Global Institution for Collaborative Research and Education (GI-CoRE), Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
³ Center for Research and Education on Drug Discovery, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

PMID: 36652724
DOI: 10.1021/acs.orglett.2c04327

Abstract

Solid-phase total synthesis of sandramycin (1), which is a C₂-symmetric cyclic decadepsipeptide natural product, and its analogues is described. On-resin ester formation and [5+5] peptide coupling allowed the preparation of a range of desymmetrized analogues. An amino acid residue that would not hamper the biological activity of 1 was successfully identified, and probe molecules and dimeric analogues were prepared on the basis of the result of the structure-activity relationship study.