posted on 2018-11-20, 17:23authored byMichael J. Varley
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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Publication date
1975
Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of the degree of Doctor of Philosophy at Loughborough University.