Electrophilic amination: Enantioselective syntheses of d-allothreonine and l-threonine
β Scribed by J.P Genet; S Juge; S Mallart
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 200 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Starting from inexpensive polyhydroxybutanoate (PHB), D-allothreonine 1 and L-threonine 2 were synthetized by a sequence involving a diastereoselective electrophilic amination. When (%I 3-hydroxybutanoic acid was protected as dioxanone? very good yield (>95 %I and high diastereomeric excess (>99 %) were obtained in the amination step.
π SIMILAR VOLUMES
The paper describes the synthesis of two epimeric tdpeptides &(L-cx-aminoadipoyl)-L-cysteinyI-D-(Omethyl)-D-threonine (13) and &(L-ct-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine ( 14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide ( 14) has be