Combinatorial Chemistry in Insects: A Library of Defensive Macrocyclic Polyamines

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Science  17 Jul 1998:
Vol. 281, Issue 5375, pp. 428-431
DOI: 10.1126/science.281.5375.428

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The pupal defensive secretion of the coccinellid beetleEpilachna borealis is composed principally of a combinatorial library of macrocyclic polyamines. These compounds constitute a previously unrecognized family of natural products, characterized by extremely large-ring lactonic structures derived from a small set of (2-hydroxyethylamino)alkanoic acids. The combinatorial assembly of these simple building blocks generates a high degree of structural diversity, which is further increased by slow, spontaneous intramolecular rearrangement of the macrocycles.

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