Labionin

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Structural formula
Structure of labionin
Structural formula of labionin
General
Surname Labionin
other names

(4 S ) -4-Amino-2 - [[[(2 R ) -2-amino-2-carboxyethyl] thio] methyl] - L -glutamic acid

Molecular formula C 9 H 17 N 3 O 6 S
External identifiers / databases
CAS number 1227469-54-6
Wikidata Q21099519
properties
Molar mass 295.31 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Labionin is a non-canonical amino acid that was first detected in 2010 in the peptide Labyrinthopeptin A2. This amino acid is characterized by its complex structure, as it has a sulfur bridge (here: a thioether ), in analogy to lanthionine , and three amino and carboxylic acid groups each. Furthermore, labionin contains three stereocenters with the configuration 2S, 4S, 8R, the position 2 being a quaternary carbon atom. Nature forms labionine from two serines and one cysteine by dehydrating the serine , adding the thiol group of the cysteine ​​to a dehydroalanine and then Michael adding a reactive intermediate to the remaining dehydroalanine. In addition, labionin has so far been detected in Labyrinthopeptin A1, Erythreapeptin and Catenulipeptin and in the peptide NAI-112.

A GCMS method is described for the detection of labionin or a degradation product of this amino acid in peptides .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ Kathrin Meindl, Timo Schmiederer, Kathrin Schneider, Andreas Reicke, Diane Butz, Simone Keller, Hans Gühring, László Vértesy, Joachim Wink, Holger Hoffmann, Mark Brönstrup, George M. Sheldrick, Roderich Süssmuth : Labyrinthopeptins: A New Class of Carbacyclic Lantibiotics . In: Angewandte Chemie International Edition. 49, 2010, p. 1151, doi: 10.1002 / anie.200905773 .
  3. ↑ Olga Genilloud, Francisca Vicente, David E. Thurston, Ana Martinez, David Rotella, Salvatore Guccione, Robin Ganellin: Drug Discovery from Natural Products . Royal Society of Chemistry, 2012, ISBN 978-1-84973-361-8 , pp. 50 ( limited preview in Google Book search).
  4. ↑ Wolfgang M. Müller, Timo Schmiederer, Paul Ensle, Roderich D. Süssmuth: In Vitro Biosynthesis of the Prepeptide of Type-III Lantibiotic Labyrinthopeptin A2 Including Formation of a C – C Bond as a Post-Translational Modification. In: Angewandte Chemie International Edition. 49, 2010, p. 2436, doi: 10.1002 / anie.200905909 .
  5. ↑ a b Alexander Pesic, Maik Henkel, Roderich D. Süssmuth: Identification of the amino acid labionin and its desulfurized derivative in the type-III lantibiotic LabA2 by means of GC / MS. In: Chemical Communications. 47, 2011, p. 7401, doi: 10.1039 / C1CC11573A .
  6. Jump up ↑ Ginka H. Völler, Joanna M. Krawczyk, Alexander Pesic, Bartlomiej Krawczyk, Jonny Nachtigall, Roderich D. Süssmuth: Characterization of New Class III Lantibiotics-Erythreapeptin, Avermipeptin and Griseopeptin from Saccharopolyspora erythraea, Streptomyus grptomyces, Streptomyces averomyces Terminal leader processing. In: ChemBioChem. 13, 2012, p. 1174, doi: 10.1002 / cbic.201200118 .
  7. ↑ H. Wang, WA van der Donk: Biosynthesis of the class III lantipeptide catenulipeptin. In: ACS Chem. Biol. 7, 2012, pp. 1529-1535, PMID 22725258 PMC 3448297 (free full text).
  8. ↑ M. Iorio, O. Sasso, SI Maffioli, R. Bertorelli, P. Monciardini, M. Sosio, F. Bonezzi, M. Summa, C. Brunati, R. Bordoni, G. Corti, G. Tarozzo, D. Piomelli, A. Reggiani, S. Donadio: A glycosylated, labionin-containing lanthipeptide with marked antinociceptive activity. In: ACS Chem. Biol. 9, 2014, pp. 398-404, PMID 24191663 .