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Marine isocyano compounds

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Marine Natural Products — Diversity and Biosynthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 167))

Abstract

Marine isocyano (-NC) terpenoids are often accompanied by isothiocyanates (R-NCS) and formamides (R-NHCHO). Recent work has uncovered the less common cyanates (R-NCO), thiocyanates (R-SCN), amines (R-NH2) and carbonimidic dichlorides (R-N=CCl2). A majority of sesquiterpenes bear one of the nitrogenous functional groups of the related -NC/-NCS/-NHCHO triad. More complex substitution exists in diterpenoid skeletons. Most complex are the kalihinols which are polyfunctional diterpenoid tetrahydrofurans or pyrans elaborating multiple isocyanoand isocyano-related functions together with hydroxyl, chloro, and olefinic groups. More recent discoveries of sesquiterpenoid isonitiles with hydroxyl and chloro substituents reinforce the speculative role of cationic intermediates in the biosynthesis of these compounds. Cyanide is incorporated into the isocyano function of terpenoids in sponges (Porifera), the phylum from which the majority of marine isocyano-related compounds have been obtained. Marine isonitriles from nudibranchs are of dietary origin. The diversity of marine isocyano-related compounds and their degree of substitution is limited by the fact that so far only isoprenoids (sesqui- and diterpenes) in certain taxa of the Porifera are involved.

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Authors and Affiliations

  1. Department of Chemistry, University of West Florida, Pensacola, FL, USA

    Clifford W. J. Chang

  2. Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii

    Paul J. Scheuer

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  1. Clifford W. J. Chang
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  2. Paul J. Scheuer
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Paul J. Scheuer

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© 1993 Springer-Verlag

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Chang, C.W.J., Scheuer, P.J. (1993). Marine isocyano compounds. In: Scheuer, P.J. (eds) Marine Natural Products — Diversity and Biosynthesis. Topics in Current Chemistry, vol 167. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0034370

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  • DOI: https://doi.org/10.1007/BFb0034370

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-56513-0

  • Online ISBN: 978-3-540-47576-7

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