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Synthetic studies toward the mannopeptimycins: synthesis of orthogonally protected beta-hydroxyenduracididines.

ABSTRACT: The asymmetric synthesis of the nonproteinogenic amino acids (2S,3S,4'S)-beta-hydroxyenduracididine 3 and (2R,3S,4'S)-beta-hydroxyenduracididine 4 in orthogonally protected form in 15 total steps from Garner's aldehyde is reported. The former and N-glycosylated form of the latter are found in the glycopeptide antibiotic mannopeptimycin.

SUBMITTER: Olivier KS

PROVIDER: S-EPMC2871400 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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Synthetic studies toward the mannopeptimycins: synthesis of orthogonally protected beta-hydroxyenduracididines.

Olivier Kevin S KS Van Nieuwenhze Michael S MS

Organic letters 20100401 8

The asymmetric synthesis of the nonproteinogenic amino acids (2S,3S,4'S)-beta-hydroxyenduracididine 3 and (2R,3S,4'S)-beta-hydroxyenduracididine 4 in orthogonally protected form in 15 total steps from Garner's aldehyde is reported. The former and N-glycosylated form of the latter are found in the glycopeptide antibiotic mannopeptimycin. ...[more]

PMID: 20232818

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