Tryptophan bisindole

Bisindole Alkaloids from Tryptophan. There are two widely different types of alkaloids derived from two tryptophan (26) units. The first is a rather small group of compounds based simply on the dimers of tryptophan which includes compounds such as calycanthine (113) (Table 10),... 

The biosynthesis of 1 follows a pattern seen for all bisindoles that have been biosynthetically investigated thus far [17, 163, 164] two molecules of L-tryptophan (123) are oxidized and then dimerized to give an initial bisindole skeleton (Fig. 24). Historically, the biosynthesis of staurosporine (121) has been investigated in parallel with that of rebeccamycin (124), a related bisindole. Both molecules are thought to be biosynthesized through nearly identical routes to give the aglycone... 

Another large group of brominated tryptophan-derived marine alkaloids are the aplysinopsins and several new examples have been reported. The sponge Hyrtios erecta has furnished 20 and 21[26], while a New Zealand asddian is the source of kottamides A-E, for example A (22) [27] and E (23) [28], The stony coral Tubastraea sp. contains the structurally complex and unprecedented bisindole tubastrindole A (24) [29]. 

Two genes appear to be essential for indolocarbazole production in actinomycetes. One of the genes encodes a tryptophan oxidase (rebO, staO), while the second one codes for a heme-containing oxidase (rebD, staD). In their absence, no bisindole intermediates can be formed [23,33]. 

The amino acid L-tryptophan (19), used as a food supplement and in insomnia, is manufactured in Japan by a novel biotechnological process that leads to the contaminant bisindole 50 (peak E) 126), for which earlier an aminal structure was proposed 127). An outbreak of an eosinophilia... 

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