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Synthesis of tryptophan stereoselectively labelled with tritium and deuterium in the β-methylene group; the steric course of hydroxylation in sporidesmin biosynthesis
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1974
Year
Steric CourseCombinatorial ChemistryBioorganic ChemistryEngineeringSide-chain HydroxylationOrganic ChemistryChemistryBiosynthesisSporidesmin BiosynthesisSporidesmin ANatural Product BiosynthesisStereoselective SynthesisBiochemistryOxazolinone MethodNatural Product SynthesisEnantioselective SynthesisBiomolecular Engineeringβ-Methylene GroupNatural SciencesSynthetic Chemistry
The (3R)- and (3S)-forms of [3-3H]tryptophan have been synthesised by the oxazolinone method and used to show that side-chain hydroxylation in the bio-synthesis of sporidesmin A takes place with retention of configuration at the site of attack.