Applied Chemistry Courses/Graduate School
Department of Material and Life Chemistry/Undergraduate

Bioactive Natural Products Chemistry Laboratory
Masahiro Okada (Professor)
Office: 23-727-1 (Extention: 3853)
Laboratory: 23-726 (Extention: 3852)
E-mail: okada＠kanagawa-u.ac.jp

Shimpei Sumimoto (Assisitant Professor)
Office: 23-727
Laboratory: 23-726 (Extention: 3852)
E-mail: sumi＠kanagawa-u.ac.jp

Masahiro Okada

Shimpei Sumimoto---------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Research Field:
Natural Products chemistry, Bioorganic Chemistry.
Research Overview: Bioactive natural products chemistry; discovery and identification, chemical synthesis, and biosynthesis
and function.
Research Subjects: 1. Studies of post-translationally modified peptides. 2. Creation of bioactive metabolites by biosynthetic
engineering．3. Discovery of novel natural products.
Research Highlights:
Studies of peptides post-translationally isoprenylated
Discovery of novel natural products from cyanobacteiraat the Trp residue
Post-translational Isoprenylated
Peptides at the Trp Residue

H 2N

HNO

H
N

H
N
H

OO

H
N

NO

N
H

O

HN

CONH2CO2H

CO2H
ComXRO-E-2 pheromone

HOH
HNNH2HOCO2H
HNH

H 2NO

NNOHNNOO

ComXnatto pheromoneON
HNOOOONH

HNNO

CONH2ONHO
HN

HO2C
H2NOC
HNNN
HHO
NH CONH2OONH
O

CO2H
Kawaguchipeptin A

Proteins and peptides are biosynthesized through RNAtranslation, and RNA is produced through DNA transcription.
The plain proteins and peptides are generally inactive andfrequently chemically modified via post-translationalmodification.
We have identified a new post-translation modification in apeptide pheromone, namely post-translational isoprenylationof the tryptophan residue. We are investigating the activation
mechanism, biological events, and universality of themodification.

Microorganisms produce various natural products such as
peptide, polyketide, terpenoids. These natural products
display interesting biological activities, which depend on theirunique structures.
We focus on cyanobacteria for isolation source of bioactive
compounds. Cyanobacteria has high species diversity.
However, limited cyanobacterial species was used in isolationof bioactive compounds. We have isolated some biologicalnatural products from cyanobacteria. We are investigating
discovery of biological natural products, structural
determination and mechanism of action.

Publications:1) K. Hirooka, S. Shioda, and M. Okada. Identification of critical residues for the catalytic activity of ComQ, a Bacillus
prenylation enzyme for quorum sensing, by using a simple bioassay system. Biosci. Biotechnol. Biochem., 2020, 84, 347–357; 2)
M. Okada, Posttranslational isoprenylation of tryptophan in bacteria", Beilstein J. Org. Chem. 2017, 13, 338–346; 3) M. Okada,et al., Genome-based discovery of an unprecedented cyclization mode in fungal sesterterpenoids biosynthesis. J. Am. Chem. Soc.,
2016, 138, 10011–10018;
1) S. Sumimoto, A. Iwasaki, O. Ohno, K. Sueyoshi, T. Teruya and K. Suenaga, Kanamienamide, an Enamide with an Enol Ether
from the Marine Cyanobacterium Moorea bouillonii, Org. Lett., 2016, 18, 4884−4887; 2) S. Sumimoto, M. Kobayashi, R. Sato,S. Shinomiya, A. Iwasaki, S. Suda, T. Teruya, T. Inuzuka, O. Ohno, and K. Suenaga, Minnamide A, a Linear Lipopeptide fromthe Marine Cyanobacterium Okeania hirsuta, Org. Lett., 2019, 21, 1187−1190.
Affiliated Academic Organizations:M. Okada: The Japan Society for Bioscience, Biotechnology, and Agrochemistry; The Chemical Society of Japan; AmericanChemical Society; The Pharmaceutical Society of Japan.
S. Sumimoto: The Chemical Society of Japan; American Chemical Society; Japanese Society for Chemical Biology.
---------------------------------------------------------------------------------------------------------------------------------------------------------Current Members; Research assistant 1, Postgraduate students 3, Undergraduate students 12.
Facilities; Microwave peptide synthesizer, Anaerobic chamber, Electroporator, HPLC systems, Low temperature chemical reactor.