Literature DB >> 17192095

Synthesis of beta-lactam scaffolds for ditopic peptidomimetics.

Claudio Palomo1, Jesus M Aizpurua, Eva Balentova, Azucena Jimenez, Joseba Oyarbide, Raluca M Fratila, José Ignacio Miranda.   

Abstract

[reaction: see text] Ring opening of alpha-substituted-alpha-methoxycarbonyl-N-nosylaziridines provides a practical access to enantiopure alpha,alpha'-disubstituted beta-lactam scaffolds, novel types of ditopic reverse turn surrogates. The procedure is general, short, and high yielding and starts from handy alpha-substituted serinates and alpha-amino acid derivatives.

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Year:  2007        PMID： 17192095     DOI： 10.1021/ol0626241

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Discovery of PF-04620110, a Potent, Selective, and Orally Bioavailable Inhibitor of DGAT-1.

Authors:  Robert L Dow; Jian-Cheng Li; Michael P Pence; E Michael Gibbs; Jennifer L LaPerle; John Litchfield; David W Piotrowski; Michael J Munchhof; Tara B Manion; William J Zavadoski; Gregory S Walker; R Kirk McPherson; Susan Tapley; Eliot Sugarman; Angel Guzman-Perez; Paul DaSilva-Jardine
Journal:  ACS Med Chem Lett       Date:  2011-03-18       Impact factor: 4.345

2.  Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary alpha-Amino Acids.

Authors:  Carlos Cativiela; Mario Ordóñez
Journal:  Tetrahedron Asymmetry       Date:  2009-01-30

3.  Enantiomerically pure trans-beta-lactams from alpha-amino acids via compact fluorescent light (CFL) continuous-flow photolysis.

Authors:  Yvette S Mimieux Vaske; Maximillian E Mahoney; Joseph P Konopelski; David L Rogow; William J McDonald
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

4.  A virtual library of constrained cyclic tetrapeptides that mimics all four side-chain orientations for over half the reverse turns in the protein data bank.

Authors:  Sage Arbor; Garland R Marshall
Journal:  J Comput Aided Mol Des       Date:  2008-09-17       Impact factor: 3.686

5.  Structural characterization of an enantiomerically pure amino acid imidazolide and direct formation of the beta-lactam nucleus from an alpha-amino acid.

Authors:  Brian S Gerstenberger; Jinzhen Lin; Yvette S Mimieux; Lauren E Brown; Allen G Oliver; Joseph P Konopelski
Journal:  Org Lett       Date:  2008-01-09       Impact factor: 6.005

6.  Route exploration and synthesis of the reported pyridone-based PDI inhibitor STK076545.

Authors:  Eric Greve; Sergey V Lindeman; Christina Scartelli; Lin Lin; Robert Flaumenhaft; Chris Dockendorff
Journal:  Org Biomol Chem       Date:  2020-08-19       Impact factor: 3.876
  6 in total

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