Partial Structure of Papiliochrome, the Yellow Wing Pigment of the Papilionid Butterflies

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Abstract
Papiliochrome II, one of the yellow wing pigments of the Papilionid butterfly, Papilio xuthus, can be split into ʟ-kynurenine and a catecholamine derivative, SN-1, by 10-3 n HCI. The latter is hydrolyzed by ɴ HCI into β-alanine and noradrenaline. The structure of SN-1 has been elucidated as N-(β-alanyl)-ʟ-noradrenaline by NMR and MS data as well as by synthesis. Preparation of the N-hydroxysuccinimide ester of benzyloxycarbonyl-β-alanine, its condensation with ʟ-noradrenaline to the corresponding benzyloxycarbonyl protected SN-1 and of N- (β-alanyl)-ʟ-noradrenaline by hydrogenolysis of the protecting group are described.

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