Literature DB >> 27533920

Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation.

Michael C Pirrung1, Fa Zhang, Sudhakar Ambadi, Y Gangadhara Rao.   

Abstract

Solution-phase syntheses of three bioactive natural products of mixed polypeptide-polyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes.

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Year:  2016        PMID： 27533920      PMCID： PMC5303010          DOI： 10.1039/c6ob01233g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  21 in total

1.  Peptide synthesis 'in water' by a solution-phase method using water-dispersible nanoparticle Boc-amino acid.

Authors:  Keiko Hojo; Hideki Ichikawa; Mare Onishi; Yoshinobu Fukumori; Koichi Kawasaki
Journal:  J Pept Sci       Date:  2011-04-14       Impact factor: 1.905

2.  Proteasome inhibition by fellutamide B induces nerve growth factor synthesis.

Authors:  John Hines; Michael Groll; Margaret Fahnestock; Craig M Crews
Journal:  Chem Biol       Date:  2008-05

3.  Structural basis of functional group activation by sulfotransferases in complex metabolic pathways.

Authors:  Jennifer Gehret McCarthy; Eli B Eisman; Sarang Kulkarni; Lena Gerwick; William H Gerwick; Peter Wipf; David H Sherman; Janet L Smith
Journal:  ACS Chem Biol       Date:  2012-09-26       Impact factor: 5.100

4.  Total synthesis of syringolin A and B.

Authors:  Michael C Pirrung; Goutam Biswas; Tannya R Ibarra-Rivera
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

5.  Synthesis of Optically Active beta-Amino Acid N-Carboxyanhydrides.

Authors: 
Journal:  Org Lett       Date:  2000-06-29       Impact factor: 6.005

6.  Fellutamide B is a potent inhibitor of the Mycobacterium tuberculosis proteasome.

Authors:  Gang Lin; Dongyang Li; Tamutenda Chidawanyika; Carl Nathan; Huilin Li
Journal:  Arch Biochem Biophys       Date:  2010-06-15       Impact factor: 4.013

7.  Aldol-type reactions of unmasked iodoacetic acid with carbonyl compounds promoted by samarium diiodide: efficient synthesis of carboxylic 3-hydroxyacids and their derivatives.

Authors:  José M Concellón; Carmen Concellón
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

8.  Stimulation of nerve growth factor synthesis and secretion by fellutamide A in vitro.

Authors:  K Yamaguchi; T Tsuji; S Wakuri; K Yazawa; K Kondo; H Shigemori; J Kobayashi
Journal:  Biosci Biotechnol Biochem       Date:  1993-02       Impact factor: 2.043

9.  Protein chemical synthesis by serine and threonine ligation.

Authors:  Yinfeng Zhang; Ci Xu; Hiu Yung Lam; Chi Lung Lee; Xuechen Li
Journal:  Proc Natl Acad Sci U S A       Date:  2013-04-08       Impact factor: 11.205

10.  Development of a method for environmentally friendly chemical peptide synthesis in water using water-dispersible amino acid nanoparticles.

Authors:  Keiko Hojo; Asaki Hara; Hiroyuki Kitai; Mare Onishi; Hideki Ichikawa; Yoshinobu Fukumori; Koichi Kawasaki
Journal:  Chem Cent J       Date:  2011-08-25       Impact factor: 4.215
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  2 in total

1.  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

Review 2.  Fungal Secondary Metabolites as Inhibitors of the Ubiquitin-Proteasome System.

Authors:  Magdalena Staszczak
Journal:  Int J Mol Sci       Date:  2021-12-10       Impact factor: 5.923
  2 in total

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