Solid-Phase Synthesis of Callipeltin D. Stereochemical Confirmation of the Unnatural Amino Acid AGDHE

Solid-Phase Synthesis of Callipeltin D. Stereochemical Confirmation of the Unnatural Amino Acid AGDHE

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-a...

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Veröffentlicht in:Organic letters 2005-12, Vol.7 (26), p.5881-5883
Hauptverfasser: Cranfill, David C, Morales-Ramos, Ángel I, Lipton, Mark A
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemistry
Animals
Depsipeptides - chemical synthesis
Guanidines - chemistry
Heptanoic Acids - chemistry
Molecular Structure
Porifera - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052438f