KEIO RESEARCHERS INFORMATION SYSTEM

Papers 【 Display / hide 】

Papers 【 Display / hide 】

• Stereodivergent Construction of trans-Decalin-Based Terpenoids

  Barlock S.L., Shved A.S., Landers K.D., Mai B.K., Fujiki S., Ryffel P.C., Lo W.Y., Feng A.G., Wade N.W., Zhu L., Nguyen V.D., Petrone D.A., Denmark S.E., Sarlah D.

  Journal of the American Chemical Society 148 ( 12 ) 13391 - 13403 2026.04

  ISSN  00027863

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  Thousands of highly oxygenated terpenoid natural products contain a common trans-decalin core bearing oxidized substituents in either the equatorial or axial configuration at the C(4) quaternary center. We report an expedient route to a versatile terpenoid building block primed for elaboration into numerous complex natural products. This intermediate is provided from (R)-carvone, a cheap and abundant chiral pool material, in three steps through a diastereodivergent, intramolecular carboborylation reaction. Notably, this method uniquely provides either equatorial or axial functionalized products from a single, common precursor. Identification of optimal ligands required extensive screening efforts, facilitated in part by high-throughput experimentation (HTE) and the construction of an algorithmically guided, combinatorial, in silico library, which identified the highest performing axial-selective ligand. The key interactions responsible for the observed high diastereoselectivity were elucidated with computational analysis, and the synthetic utility of this method was demonstrated in the total synthesis of several diterpenoid natural products.

  • Access to Document (DOI)

• Efficient Peptide Synthesis Catalyzed by Organic Selenium Compounds

  Fujiki S.

  Yuki Gosei Kagaku Kyokaishi Journal of Synthetic Organic Chemistry 84 ( 7 ) 686 - 687 2026

  ISSN  00379980

  • Access to Document (DOI)

• A Versatile Enzymatic Pathway for Modification of Peptide C-Termini

  Dommaraju S.R., Kandy S.K., Ren H., Luciano D.P., Fujiki S., Sarlah D., Zhao H., Chekan J.R., Mitchell D.A.

  ACS Central Science 11 ( 11 ) 2143 - 2153 2025.11

  ISSN  23747943

  　View Summary

  Advances in bioinformatics have enabled the discovery of unique enzymatic reactions, particularly for ribosomally synthesized and post-translationally modified peptides (RiPPs). The recently discovered daptides, peptides with their C-terminus replaced by an amine, represent one such case, but the diversity, requirements, and engineering potential of daptide biosynthesis remain to be established. Using the daptide biosynthetic gene clusters from Thermobifida fusca and Streptomyces azureus, we reconstituted daptide biosynthesis in vitro, revealing the enzymatic requirements for successive oxidative decarboxylation, transamination, and N,N-dimethylation. In vitro and in vivo studies showed a tailoring family of YcaO enzymes convert a secondary amine intermediate to a C-terminal imidazoline. We further demonstrated enzymatic activity toward shortened, leader peptide-free, and non-native core peptides, highlighting a broad substrate tolerance. Using these insights, we directed the daptide pathway to install new C-termini, including a bioconjugation-compatible aminoacetone, on various peptide and protein substrates.

  • Access to Document (DOI)

Research Projects of Competitive Funds, etc. 【 Display / hide 】

Research Projects of Competitive Funds, etc. 【 Display / hide 】

• 多重結合のヒドロビスマス化を基盤とする新規反応の開拓

  2025.07

  -

  2027.03

  研究活動スタート支援, Principal investigator

Courses Taught 【 Display / hide 】

Courses Taught 【 Display / hide 】

• LABORATORIES IN APPLIED CHEMISTRY B

  2026

• LABORATORIES IN BASIC CHEMISTRY

  2026

• LABORATORIES IN BASIC CHEMISTRY

  2025

• LABORATORIES IN APPLIED CHEMISTRY B

  2025