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Stereochemistry and Conformation of Skyllamycin, a Non-Ribosomally Synthesized Peptide from Streptomyces sp Acta 2897
Technical University of Berlin, Germany .
Linköping University, Department of Physics, Chemistry and Biology. Linköping University, The Institute of Technology. University of Limoges, France.
Technical University of Berlin, Germany University of Evry Val dEssonne, France CNRS, France CEA, France .
Sanofi, Germany .
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2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 17, 4948-4955 p.Article in journal (Refereed) Published
Abstract [en]

Skyllamycin is a non-ribosomally synthesized cyclic depsipeptide from Streptomyces sp. Acta 2897 that inhibits PDGF-signaling. The peptide scaffold contains an N-terminal cinnamoyl moiety, a -methylation of aspartic acid, three -hydroxylated amino acids and one rarely occurring -hydroxy glycine. With the exception of -hydroxy glycine, the stereochemistry of the amino acids was assigned by comparison to synthetic reference amino acids applying chiral GC-MS and Marfey-HPLC analysis. The stereochemistry of -hydroxy glycine, which is unstable under basic and acidic conditions, was determined by conformational analysis, employing a combination of data from NOESY-NMR spectroscopy, simulated annealing and free MD simulations. The simulation procedures were applied for both R- and S-configured -hydroxy glycine of the skyllamycin structure and compared to the NOESY data. Both methods, simulated annealing and free MD simulations independently support S-configured -hydroxy glycine thus enabling the assignment of all stereocenters in the structure of skyllamycin and devising the role of two-component flavin dependent monooxygenase (Sky39) as S-selective.

Place, publisher, year, edition, pages
Wiley-VCH Verlag , 2014. Vol. 20, no 17, 4948-4955 p.
Keyword [en]
conformational analysis; NOESY-NMR spectroscopy; peptide antibiotics; skyllamycin; structure elucidation
National Category
Medical and Health Sciences
URN: urn:nbn:se:liu:diva-107854DOI: 10.1002/chem.201304562ISI: 000334396900014OAI: diva2:727694
Available from: 2014-06-23 Created: 2014-06-23 Last updated: 2014-06-23

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Department of Physics, Chemistry and BiologyThe Institute of Technology
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Chemistry - A European Journal
Medical and Health Sciences

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