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Collect. Czech. Chem. Commun. 2009, 74, 901-925
https://doi.org/10.1135/cccc2009017
Published online 2009-05-19 11:33:09

Synthesis of Aib-containing cyclopeptides via the ‘azirine/oxazolone method’

Ingeborg Dannecker-Dörig, Anthony Linden and Heinz Heimgartner*

Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Crossref Cited-by Linking

  • Bucher Christoph B., Linden Anthony, Heimgartner Heinz: Synthesis and Solid State Conformation of Tetrapeptide Amides Containing two Aib and two (αMe)Phe Residues – Use of Enantiomerically Pure 2‐Benzyl‐2‐methyl‐2H‐azirin‐3‐amines as (αMe)Phe‐Synthons. Chemistry & Biodiversity 2020, 17. <https://doi.org/10.1002/cbdv.202000246>
  • Linden Anthony, Magirius J. E. Florian, Heimgartner Heinz: Solid-state conformations of linear depsipeptide amides with an alternating sequence of α,α-disubstituted α-amino acid and α-hydroxy acid. Acta Crystallogr C Struct Chem 2020, 76, 1. <https://doi.org/10.1107/S2053229619016073>
  • Crisma Marco, Formaggio Fernando, Alemán Carlos, Torras Joan, Ramakrishnan Chandrasekharan, Kalmankar Neha, Balaram Padmanabhan, Toniolo Claudio: The fully‐extended conformation in peptides and proteins. Peptide Science 2018, 110. <https://doi.org/10.1002/bip.23100>
  • Heimgartner Heinz, Strässler Christoph, Linden Anthony: Synthesis of Tripeptides Containing Heterocyclic α-Amino Acids by Using Heterospirocyclic 3-Amino-2H-azirines. HETEROCYCLES 2018, 97, 333. <https://doi.org/10.3987/COM-18-S(T)22>
  • Toniolo Claudio, Crisma Marco, Formaggio Fernando, Alemán Carlos, Ramakrishnan Chandrasekharan, Kalmankar Neha, Balaram Padmanabhan: Intramolecular backbone···backbone hydrogen bonds in polypeptide conformations. The other way around: ɛ‐turn. Biopolymers 2017, 108. <https://doi.org/10.1002/bip.22911>
  • Crisma Marco, Toniolo Claudio: Helical screw‐sense preferences of peptides based on chiral, Cα‐tetrasubstituted α‐amino acids. Biopolymers 2015, 104, 46. <https://doi.org/10.1002/bip.22581>
  • Arnhold Franziska S., Linden Anthony, Heimgartner Heinz: Synthesis of Aib‐ and Phe(2Me)‐Containing Cyclopentapeptides. Helvetica Chimica Acta 2015, 98, 155. <https://doi.org/10.1002/hlca.201400323>
  • Arnhold Franziska S., Linden Anthony, Heimgartner Heinz: Synthesis of Cyclopentapeptides with Three to Five Aib Units. Helvetica Chimica Acta 2015, 98, 232. <https://doi.org/10.1002/hlca.201400359>
  • Arnhold Franziska S., Linden Anthony, Heimgartner Heinz: Synthesis of Z‐Protected Aib‐ and Phe(2Me)‐Containing Pentapeptides and Their Crystal Structures. Helvetica Chimica Acta 2014, 97, 619. <https://doi.org/10.1002/hlca.201400084>
  • Stoykova Svetlana A., Linden Anthony, Heimgartner Heinz: A novel 2H-azirin-3-amine as a synthon for a sulfur-containing dipeptide segment. Journal of Sulfur Chemistry 2014, 35, 14. <https://doi.org/10.1080/17415993.2013.774401>
  • Blaser Pia, Altherr Werner, Linden Anthony, Heimgartner Heinz: Attempts toward the Synthesis of the Peptaibol Antiamoebin by Using the ‘Azirine/Oxazolone Method’. Chemistry & Biodiversity 2013, 10, 920. <https://doi.org/10.1002/cbdv.201200386>
  • Stoykova Svetlana A., Linden Anthony, Heimgartner Heinz: Highly Constrained Linear Oligopeptides Containing Heterocyclic α‐Amino Carboxylic Acids. Helvetica Chimica Acta 2013, 96, 1714. <https://doi.org/10.1002/hlca.201300062>
  • Khlebnikov Alexander F., Novikov Mikhail S.: Recent advances in 2H-azirine chemistry. Tetrahedron 2013, 69, 3363. <https://doi.org/10.1016/j.tet.2013.02.020>
  • Stoykova Svetlana A., Linden Anthony, Heimgartner Heinz: Synthesis of Aib‐Pro Oligopeptides by Repeated Azirine Coupling with the Aib‐Pro Synthon. Helvetica Chimica Acta 2012, 95, 1325. <https://doi.org/10.1002/hlca.201200136>
  • Dannecker‐Dörig Ingeborg, Linden Anthony, Heimgartner Heinz: Synthesis of Poly‐Aib Oligopeptides and Aib‐Containing Peptides via the ‘Azirine/Oxazolone Method’, and Their Crystal Structures. Helvetica Chimica Acta 2011, 94, 993. <https://doi.org/10.1002/hlca.201100116>
  • Heimgartner Heinz, Löpfe Michael, Linden Anthony: N-Methyl-N-phenyl-5-oxa-1-azaspiro[2.5]oct-1-en-2-amine — Synthesis and Reactions of a Synthon for an Unknown α-Amino Acid. HETEROCYCLES 2010, 82, 1267. <https://doi.org/10.3987/COM-10-S(E)73>