Termination of the structural confusion between plipastatin A1 and fengycin IX.

Abstract

Plipastatin A1 and fengycin IX were experimentally proven to be identical compounds, while these had been considered as diastereomers due to the permutation of the enantiomeric pair of Tyr in most papers. The (1)H NMR spectrum changed to become quite similar to that of plipastatin A1, when the sample which provided resembled spectrum of fengycin IX was treated with KOAc followed by LH-20 gel filtration. Our structural investigations disclosed that the structures of these molecules should be settled into that of plipastatin A1 by Umezawa (L-Tyr4 and D-Tyr10).

• Authors: Miho Honma, Kazuaki Tanaka, Katsuhiro Konno, Kenji Tsuge, Toshikatsu Okuno, Masaru Hashimoto
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 20 Issue 12 Pg. 3793-8 (Jun 15 2012) ISSN: 1464-3391 [Electronic] England
• PMID: 22609073 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 Elsevier Ltd. All rights reserved.

Chemical References

• Fatty Acids
• Oligopeptides
• Peptides, Cyclic
• fengycin IX
• plipastatin

Topics

• Bacillus subtilis (chemistry, isolation & purification)
• Fatty Acids (chemistry)
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Oligopeptides (chemistry)
• Peptides, Cyclic (chemistry)
• Stereoisomerism