210345-08-7Relevant articles and documents
Synthesis of novel unsaturated bicyclic lactams by ring-closing metathesis
Grossmith, Catharine E.,Senia, Francesco,Wagner, Jürgen
, p. 1660 - 1662 (1999)
An efficient and versatile synthetic method for the preparation of novel unsaturated fused bicyclic lactams is described. The crucial step of the stereoselective approach is the ting-closing metathesis reaction. The 6,5-, 7,5- and 8,5-fused 1-aza-2-oxobicycloalkenes can be obtained in five steps and good overall yield.
Synthesis and evaluation of a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane scaffold as a mimic of Xaa-trans-Pro in poly-l-proline type II helix conformation
Aillard, Boris,Kilburn, Jeremy D.,Blaydes, Jeremy P.,Tizzard, Graham J.,Findlow, Stuart,Werner, J?rn M.,Bloodworth, Sally
, p. 4562 - 4569 (2015/04/14)
We describe the development of a small-molecule mimic of Xaa-trans-Pro dipeptide in poly-l-proline type II helix conformation, based upon a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane core structure. Stereoselective synthesis of the mimic from l-pyroglutamic acid is achieved in twelve linear steps and 9.9% yield. Configurational and conformational analyses are conducted using a combination of 1H NMR spectroscopy, X-ray crystallography and circular dichroism spectroscopy; and evaluation of the mimic as a promising surrogate dipeptide, in a protein-protein interaction between the SH3 domain of human Fyn kinase (Fyn SH3) and peptidomimetics of its biological ligand, are conducted by 1H-15N HSQC NMR titration experiments.
Synthesis of hydrophobic phase-tagged prolyl peptides featuring rapid reaction/separation
Chiba, Kazuhiro,Sugihara, Mari,Yoshida, Kazumi,Mikami, Yuzuru,Kim, Shokaku
experimental part, p. 8014 - 8020 (2009/12/06)
Hydrophobically tagged prolyl peptides were synthesized using an electrochemically modified prolyl moiety. The hydrophobic tag served a useful handle for the repetitive reaction/separation steps during solution-phase peptide synthesis. Furthermore, the ta
A new spirocyclic proline-based lactam as efficient type II′ β-turn inducing peptidomimetic
Lesma, Giordano,Colombo, Alessia,Sacchetti, Alessandro,Silvani, Alessandra
body text, p. 7423 - 7425 (2009/05/11)
A new proline-based spirotricyclic lactam is reported as an efficient type II′ β-turn inducing peptidomimetic. After investigations of the reverse turn properties by computational techniques, the scaffold has been synthesized by a straightforward sequence relying on a key RCM reaction for the construction of the spirocyclic lactams ring. For its conformational properties, the scaffold can be considered a privileged structure to be employed as a mimic of the β-turn motif of the potent antibiotic Gramicidin S.
Synthesis of new bicyclic lactam peptidomimetics by ring-closing metathesis reactions
Colombo, Lino,Di Giacomo, Marcello,Vinci, Valerio,Colombo, Matteo,Manzoni, Leonardo,Scolastico, Carlo
, p. 4501 - 4513 (2007/10/03)
An efficient and versatile synthetic method for the preparation of new fused bicyclic lactams 3a and 3b is described. The spirane cyclopentane nucleus was easily installed by diallylation of the pyroglutamate derivative 18 followed by ring-closing metathe
A sequential electrochemical oxidation - Olefin metathesis strategy for the construction of bicyclic lactam based peptidomimetics
Beal, Laura M.,Moeller, Kevin D.
, p. 4639 - 4642 (2007/10/03)
A sequential electrochemical amide oxidation - ring closing olefin metathesis sequence has been used to overcome problems associated with the synthesis of seven-membered ring lactam containing bicyclic peptidomimetics. The synthesis of several previously unavailable bicyelic lactam building blocks for constructing constrained thyroliberin analogs is described.
