Literature DB >> 20676223

Design and Synthesis of Functionalized Trisaccharides as p53-Peptide Mimics.

Kaori Sakurai1, Daniel Kahne.   

Abstract

Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an α-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology.

Entities:  

Year:  2010        PMID： 20676223      PMCID： PMC2911623          DOI： 10.1016/j.tetlet.2010.05.012

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  12 in total

1.  Conformation Design of Open-Chain Compounds.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-06-16       Impact factor: 15.336

2.  Discovery of potent antagonists of the interaction between human double minute 2 and tumor suppressor p53.

Authors:  C García-Echeverría; P Chène; M J Blommers; P Furet
Journal:  J Med Chem       Date:  2000-08-24       Impact factor: 7.446

3.  Discovery and cocrystal structure of benzodiazepinedione HDM2 antagonists that activate p53 in cells.

Authors:  Bruce L Grasberger; Tianbao Lu; Carsten Schubert; Daniel J Parks; Theodore E Carver; Holly K Koblish; Maxwell D Cummings; Louis V LaFrance; Karen L Milkiewicz; Raul R Calvo; Diane Maguire; Jennifer Lattanze; Carol F Franks; Shuyuan Zhao; Kannan Ramachandren; Gwendolyn R Bylebyl; Marie Zhang; Carl L Manthey; Eugene C Petrella; Michael W Pantoliano; Ingrid C Deckman; John C Spurlino; Anna C Maroney; Bruce E Tomczuk; Christopher J Molloy; Roger F Bone
Journal:  J Med Chem       Date:  2005-02-24       Impact factor: 7.446

4.  Structure of the MDM2 oncoprotein bound to the p53 tumor suppressor transactivation domain.

Authors:  P H Kussie; S Gorina; V Marechal; B Elenbaas; J Moreau; A J Levine; N P Pavletich
Journal:  Science       Date:  1996-11-08       Impact factor: 47.728

Review 5.  Carbohydrates in peptide and protein design.

Authors:  Knud J Jensen; Jesper Brask
Journal:  Biopolymers       Date:  2005       Impact factor: 2.505

Review 6.  Carbohydrates as scaffolds in drug discovery.

Authors:  Wim Meutermans; Giang Thanh Le; Bernd Becker
Journal:  ChemMedChem       Date:  2006-11       Impact factor: 3.466

7.  Use of a retroinverso p53 peptide as an inhibitor of MDM2.

Authors:  Kaori Sakurai; Hak Suk Chung; Daniel Kahne
Journal:  J Am Chem Soc       Date:  2004-12-22       Impact factor: 15.419

8.  Structure-activity studies in a family of beta-hairpin protein epitope mimetic inhibitors of the p53-HDM2 protein-protein interaction.

Authors:  Rudi Fasan; Ricardo L A Dias; Kerstin Moehle; Oliver Zerbe; Daniel Obrecht; Peer R E Mittl; Markus G Grütter; John A Robinson
Journal:  Chembiochem       Date:  2006-03       Impact factor: 3.164

9.  In vivo activation of the p53 pathway by small-molecule antagonists of MDM2.

Authors:  Lyubomir T Vassilev; Binh T Vu; Bradford Graves; Daisy Carvajal; Frank Podlaski; Zoran Filipovic; Norman Kong; Ursula Kammlott; Christine Lukacs; Christian Klein; Nader Fotouhi; Emily A Liu
Journal:  Science       Date:  2004-01-02       Impact factor: 47.728

10.  X-ray crystal structure of galabiose, O-alpha-D-galactopyranosyl-(1---4)-D-galactopyranose.

Authors:  G Svensson; J Albertsson; C Svensson; G Magnusson; J Dahmén
Journal:  Carbohydr Res       Date:  1986-01-15       Impact factor: 2.104
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