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Solid-phase synthesis of callipeltin D. Stereochemical confirmation of the unnatural amino acid AGDHE.

ABSTRACT: [structure: see text] The lipopeptide callipeltin D (1) was synthesized using an Fmoc-based solid-phase strategy in seven steps and 35% overall yield. The 1H NMR of synthetic 1 correlated closely with that of the natural product, confirming the configurational assignment of the novel amino acid constituent (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid.

SUBMITTER: Cranfill DC

PROVIDER: S-EPMC1635142 | biostudies-literature | 2005 Dec

REPOSITORIES: biostudies-literature

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Solid-phase synthesis of callipeltin D. Stereochemical confirmation of the unnatural amino acid AGDHE.

Cranfill David C DC Morales-Ramos Angel I AI Lipton Mark A MA

Organic letters 20051201 26

[structure: see text] The lipopeptide callipeltin D (1) was synthesized using an Fmoc-based solid-phase strategy in seven steps and 35% overall yield. The 1H NMR of synthetic 1 correlated closely with that of the natural product, confirming the configurational assignment of the novel amino acid constituent (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid. ...[more]

PMID: 16354090

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