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 μg/mL, without detectable toxicity even at a high concentration of 10 μg/mL. Two isocyanides had EC50 values of 0.23 and 0.25 μg/mL, comparable to that of CuSO4, which is used as a fouling inhibitor (EC50 = 0.27 μg/mL).
Highlights
Many essential human activities, such as transportation and fishing, are carried out in the ocean, and submarine structures—seawater intakes pipes for power plants, breeding nets, and so on—are widely used
Steps were required for the total synthesis of
Improved by further optimization, the synthetic scheme seems to be a reliable one for the synthesis
Summary
Many essential human activities, such as transportation and fishing, are carried out in the ocean, and submarine structures—seawater intakes pipes for power plants, breeding nets, and so on—are widely used. In current research on green antifouling agents [16], natural products obtained from marine of 1 and examined the biological activity of a synthetic sample against the same cypris larvae, creatures have attracted much attention [17,18,19,20,21,22,23,24]. Our group achieved These the first results total synthesis of 1 and examined the the isocyano biological activity of a syntheticproperties. Obtained from crustaceans such as crabs and shrimp as a cheap and abundant biomass platform, the compound, which derived from possesses a sugar-based structure, was expected to have through organicissynthesis, because an amino group, which is essential for introduction of low toxicity. (b) Synthetic plan for glucosamine‐based isocyanides. properties, along with their antifouling activities. (b) Synthetic plan for glucosamine-based isocyanides
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have