Synthetic examination of incorrectly proposed structures of biomolecules

Abstract

Many incorrect structures of biomolecules have been proposed for natural products. Synthesis of compounds having the proposed structures often enabled us to judge the correctness of the proposals. In some cases, we were able to revise the structures by synthesizing the biomolecules themselves. In other cases, we were able to definitely disprove the proposed structures. Some examples treated in this review include: auxin-a and b; the sex pheromone of Chlamydomonas; sex pheromones of the gypsy moth, the American cockroach, and the pink bollworm moth; Persoons' periplanone-A; orobanchol; naurol A; bifurcarenone; koninginin A; alpha-acoradiene; himachalene-type pheromones of the flea beetle; differolide; blattellastanoside A and B; etc.

Biosynthesis of (±)-Differolide, an Antioxidant Isolate from Streptomyces qaidamensis S10T

“…This suggested that the compound was definitely an antioxidant that may have the effect of enabling S. qaidamensis to survive in desert niche. In a previous study, (±)-differolide, the compound was proposed to be a biol regulator, with biological activity of promoting growth of Streptomyces aerial hypha spore maturation [19]. However, such bioactivity has not been supported by experim evidence.…”

“…Compound 1 was a pale yellow solid: In a previous study, (±)-differolide, the compound was proposed to be a biological regulator, with biological activity of promoting growth of Streptomyces aerial hyphae and spore maturation [19]. However, such bioactivity has not been supported by experimental evidence.…”

Pheromones in Chemical Communication

“…5 Although this was an extreme case of incorrect structural proposal, small mistakes took place frequently, which could be corrected by synthetic works. 6 Thanks to the development of microanalytical techniques, a small amount of a pheromone sample is sufficient for the structure determination. Compounds 1, 11-13 are depicted as examples in Table 5.1.…”