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Enzymatic Synthesis of Papiliochrome II

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Kynurenine and Serotonin Pathways

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 294))

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Abstract

Papiliochrome II is the pale yellow pigment in the wings of Papilio butterflies. The structure has been reported to be Nar- [α-(3-amino-propionyl-aminomethyl)-3, 4-dihydroxybenzyl]-L-kynurenine, which consists of one molecule each of L-kynurenine and N-β-alanyldopamine (NBAD) (Rembold and Umebachi, 1984). There are two kinds of isomers with different optical activity, called IIA and lib. Both isomers readily decompose to L-kynurenine and N-β-alanylnorepinephrine (NBANE) by being heated in 102 N HC1 at 100°C for 2 hr. The latter compound decomposes further to ß-alanine and (±)-norepine-phrine by being heated in 1 N HC1 at 100°C for 2 hr (Umebachi and Yamashita, 1977; Umebachi, 1985). The structure of this pigment is interesting in that the aromatic amino group of kynurenine is bonded to the β-carbon of the side chain of catecholamine.

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References

  • Ishizaki, Y., and Umebachi, Y., 1988, Level changes of β-alanine, dopamine, and N-β-alanyldopamine during the pupal stage of Papilio xuthus (Lepidop-tera: Papilionidae), Comp. Biochem. Physiol., 90C: 83–87.

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© 1991 Plenum Press, New York

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Umebachi, Y., Yokoyama, T. (1991). Enzymatic Synthesis of Papiliochrome II. In: Schwarcz, R., Young, S.N., Brown, R.R. (eds) Kynurenine and Serotonin Pathways. Advances in Experimental Medicine and Biology, vol 294. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5952-4_69

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  • DOI: https://doi.org/10.1007/978-1-4684-5952-4_69

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-5954-8

  • Online ISBN: 978-1-4684-5952-4

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