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The biosynthesis of fungal metabolites derived from tryptophan
The synthesis of 3-formylindole labelled in the formyl group with deuterium or tritium has been achieved via pyrolysis of the deuteriated or tritiated anilinium salt of indole-3-glyoxylic acid. The, labelled aldehydes have been used to prepare tryptophan stereoselectively labelled with deuterium or...
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| Format: | Default Thesis |
| Published: |
1975
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| Subjects: | |
| Online Access: | https://hdl.handle.net/2134/36121 |
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| Summary: | The synthesis of 3-formylindole labelled in the formyl group with deuterium or tritium has been achieved via pyrolysis of the deuteriated or tritiated anilinium salt of indole-3-glyoxylic acid. The, labelled aldehydes have been used to prepare tryptophan stereoselectively labelled with deuterium or tritium in the β-methylene group by the oxazolinone method. The configurations of the labelled tryptophans were established by 1H n.m.r. spectroscopy of the deuteriated compounds and by chemical and enzymic degradation of the tritiated compounds to fumaric acid via 4,7-dihydrotryptophan and aspartic and malic acids. In addition, biosynthetic conversion of the tritiated compounds into the antibiotic indolmycin has confirmed the assignments of configuration and established stereochemical purities of ca. 94%. [Continues.] |
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