Literature DB >> 15200308

Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue.

Oleg V Larionov1, Armin de Meijere.   

Abstract

[reaction: see text] Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue have been accomplished in high overall yields (32% for belactosin A from the amino acid 10, and 35 and 36% for belactosin C and its homoanalogue, respectively). This concise approach comprises a novel sequential acylation/beta-lactonization reaction and allows a facile alteration of the substituents, thus providing a flexible route to a new family of highly active belactosin-based proteasome inhibitors.

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Year:  2004        PMID： 15200308     DOI： 10.1021/ol049409+

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


  6 in total

1.  Inhibitor-binding mode of homobelactosin C to proteasomes: new insights into class I MHC ligand generation.

Authors:  Michael Groll; Oleg V Larionov; Robert Huber; Armin de Meijere
Journal:  Proc Natl Acad Sci U S A       Date:  2006-03-13       Impact factor: 11.205

2.  A strategy for dual inhibition of the proteasome and fatty acid synthase with belactosin C-orlistat hybrids.

Authors:  Mingzhao Zhu; Wayne D Harshbarger; Omar Robles; Joanna Krysiak; Kenneth G Hull; Sung Wook Cho; Robyn D Richardson; Yanyan Yang; Andres Garcia; Lindsey Spiegelman; Bianca Ramirez; Christopher T Wilson; Ju Anne Yau; James T Moore; Caitlen B Walker; James C Sacchettini; Wenshe R Liu; Stephan A Sieber; Jeffrey W Smith; Daniel Romo
Journal:  Bioorg Med Chem       Date:  2017-01-19       Impact factor: 3.641

3.  The effect of new proteasome inhibitors, belactosin A and C, on protein metabolism in isolated rat skeletal muscle.

Authors:  T Muthny; M Kovarik; L Sispera; A de Meijere; O V Larionov; I Tilser; M Holecek
Journal:  J Physiol Biochem       Date:  2009-06       Impact factor: 4.158

4.  Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors.

Authors:  Grace E Hubbell; Jetze J Tepe
Journal:  RSC Chem Biol       Date:  2020-09-16

5.  Cystargolide-based amide and ester Pz analogues as proteasome inhibitors and anti-cancer agents.

Authors:  Carlos R Viera; Bradley T Stevens; Talysa Viera; Cameron Zielinski; Lee A Uranga; Snezna Rogelj; Praveen L Patidar; Rodolfo Tello-Aburto
Journal:  R Soc Open Sci       Date:  2022-09-28       Impact factor: 3.653

6.  Peptide and Peptide-Like Modulators of 20S Proteasome Enzymatic Activity in Cancer Cells.

Authors:  Carlos García-Echeverría
Journal:  Int J Pept Res Ther       Date:  2006-03-04       Impact factor: 1.931
  6 in total

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