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Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Environmental Science / Faculty of Environmental Earth Science >
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Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides
This item is licensed under:Creative Commons Attribution 3.0 Unported
| Title: | Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides |
| Authors: | Umezawa, Taiki Browse this author →KAKEN DB | | Hasegawa, Yuki Browse this author | | Novita, Ira S. Browse this author | | Suzuki, Junya Browse this author | | Morozumi, Tatsuya Browse this author →KAKEN DB | | Nogata, Yasuyuki Browse this author | | Yoshimura, Erina Browse this author | | Matsuda, Fuyuhiko Browse this author →KAKEN DB |
| Keywords: | antifouling | | glucosamine | | isocyanide |
| Issue Date: | Jul-2017 |
| Publisher: | MDPI |
| Journal Title: | Marine drugs |
| Volume: | 15 |
| Issue: | 7 |
| Start Page: | 203 |
| Publisher DOI: | 10.3390/md15070203 |
| Abstract: | Biofouling, an undesirable accumulation of organisms on sea-immersed structures such as ship hulls and fishing nets, is a serious economic issue whose effects include oil wastage and clogged nets. Organotin compounds were utilized since the 1960s as an antifouling material; however, the use of such compounds was later banned by the International Maritime Organization (IMO) due to their high toxicity toward marine organisms, resulting in masculinization and imposex. Since the ban, there have been extensive efforts to develop environmentally benign antifoulants. Natural antifouling products obtained from marine creatures have been the subject of considerable attention due to their potent antifouling activity and low toxicity. These antifouling compounds often contain isocyano groups, which are well known to have natural antifouling properties. On the basis of our previous total synthesis of natural isocyanoterpenoids, we envisaged the installation of an isocyano functional group onto glucosamine to produce an environmentally friendly antifouling material. This paper describes an effective synthetic method for various glucosamine-based isocyanides and evaluation of their antifouling activity and toxicity against cypris larvae of the barnacle Amphibalanus amphitrite. Glucosamine isocyanides with an ether functionality at the anomeric position exhibited potent antifouling activity, with EC50 values below 1 mu g/mL, without detectable toxicity even at a high concentration of 10 mu g/mL. Two isocyanides had EC50 values of 0.23 and 0.25 mu g/mL, comparable to that of CuSO4, which is used as a fouling inhibitor (EC50 = 0.27 mu g/mL). |
| Rights: | http://creativecommons.org/licenses/by/3.0/ |
| Relation: | http://www.mdpi.com/1660-3397/15/7/203 |
| Type: | article |
| URI: | http://hdl.handle.net/2115/67135 |
| Appears in Collections: | 環境科学院・地球環境科学研究院 (Graduate School of Environmental Science / Faculty of Environmental Earth Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 梅澤 大樹
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