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Isocyanides Derived from α , α ‐Disubstituted Amino Acids: Synthesis and Antifouling Activity Assessment
Author(s) -
Inoue Yuki,
Takashima Shuhei,
Nogata Yasuyuki,
Yoshimura Erina,
Chiba Kazuhiro,
Kitano Yoshikazu
Publication year - 2018
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201700571
Subject(s) - biofouling , chemistry , balanus , valine , methionine , toxicity , amino acid , phenylalanine , environmentally friendly , environmental chemistry , larva , organic chemistry , biochemistry , biology , ecology , membrane
Herein, we contribute to the development of environmentally friendly antifoulants by synthesizing eighteen isocyanides derived from α , α ‐disubstituted amino acids and evaluating their antifouling activity/toxicity against the cypris larvae of the Balanus amphitrite barnacle. Almost all isocyanides showed good antifouling activity without significant toxicity and exhibited EC 50 values of 0.07 – 7.30 μg/mL after 120‐h exposure. The lowest EC 50 values were observed for valine‐, methionine‐, and phenylalanine‐derived isocyanides, which achieved > 95% cypris larvae settlement inhibition at concentrations of less than 30 μg/mL without exhibiting significant toxicity. Thus, the prepared isocyanides should be useful for further research focused on the development of environmentally friendly antifouling agents.