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Literature DB >> 21699139

New synthetic methodology for the construction of 7-substituted farnesyl diphosphate analogs.

Abstract

Through the use of a 1,2-metalate rearrangement, six 7-substituted farnesol analogs were generated in a concise manner. This new synthetic route allowed us to quickly prepare several diverse farnesyl diphosphate analogs with interesting biological activities against mammalian protein-farnesyl transferase.

Entities: Chemical Disease Gene Species

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Year: 2011 PMID： 21699139 PMCID： PMC3401630 DOI： 10.1021/ol201069x

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

14 in total

1. Synthesis of 7-substituted farnesyl diphosphate analogues.

Authors: Diwan S Rawat; Richard A Gibbs
Journal: Org Lett Date: 2002-09-05 Impact factor: 6.005

2. Crystallographic analysis of CaaX prenyltransferases complexed with substrates defines rules of protein substrate selectivity.

Authors: T Scott Reid; Kimberly L Terry; Patrick J Casey; Lorena S Beese
Journal: J Mol Biol Date: 2004-10-15 Impact factor: 5.469

3. A succinct method for preparing the Stork-Jung vinylsilane robinson annulation reagent.

Authors: Jeananne A Singletary; Hubert Lam; Gregory B Dudley
Journal: J Org Chem Date: 2005-01-21 Impact factor: 4.354

Review 4. Chemistry in living systems.

Authors: Jennifer A Prescher; Carolyn R Bertozzi
Journal: Nat Chem Biol Date: 2005-06 Impact factor: 15.040

5. Evaluation of alkyne-modified isoprenoids as chemical reporters of protein prenylation.

Authors: Amanda J DeGraw; Charuta Palsuledesai; Joshua D Ochocki; Jonathan K Dozier; Stepan Lenevich; Mohammad Rashidian; Mark D Distefano
Journal: Chem Biol Drug Des Date: 2010-10-11 Impact factor: 2.817

Review 6. Lipid posttranslational modifications. Farnesyl transferase inhibitors.

Authors: Andrea D Basso; Paul Kirschmeier; W Robert Bishop
Journal: J Lipid Res Date: 2005-11-08 Impact factor: 5.922

7. Highly efficient, general procedure for the preparation of alkylzinc reagents from unactivated alkyl bromides and chlorides.

Authors: Shouquan Huo
Journal: Org Lett Date: 2003-02-20 Impact factor: 6.005

8. Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement.

Authors: Agnès Pommier; Viatcheslav Stepanenko; Krzysztof Jarowicki; Philip J Kocienski
Journal: J Org Chem Date: 2003-05-16 Impact factor: 4.354

Review 9. The growing impact of click chemistry on drug discovery.

Authors: Hartmuth C Kolb; K Barry Sharpless
Journal: Drug Discov Today Date: 2003-12-15 Impact factor: 7.851

10. Farnesyl diphosphate analogues with omega-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions.

Authors: Guillermo R Labadie; Rajesh Viswanathan; C Dale Poulter
Journal: J Org Chem Date: 2007-11-03 Impact factor: 4.354

8 in total

New synthetic methodology for the construction of 7-substituted farnesyl diphosphate analogs.

1. Synthesis of 7-substituted farnesyl diphosphate analogues.

2. Crystallographic analysis of CaaX prenyltransferases complexed with substrates defines rules of protein substrate selectivity.

3. A succinct method for preparing the Stork-Jung vinylsilane robinson annulation reagent.

Review 4. Chemistry in living systems.

5. Evaluation of alkyne-modified isoprenoids as chemical reporters of protein prenylation.

Review 6. Lipid posttranslational modifications. Farnesyl transferase inhibitors.

7. Highly efficient, general procedure for the preparation of alkylzinc reagents from unactivated alkyl bromides and chlorides.

8. Synthesis of (+)-manoalide via a copper(I)-mediated 1,2-metalate rearrangement.

Review 9. The growing impact of click chemistry on drug discovery.

10. Farnesyl diphosphate analogues with omega-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions.

1. Sensing Enzymatic Activity by Exposure and Selection of DNA-Encoded Probes.

Review 2. Exploring protein lipidation with chemical biology.

3. Chemoenzymatic reversible immobilization and labeling of proteins without prior purification.

4. Analogs of farnesyl diphosphate alter CaaX substrate specificity and reactions rates of protein farnesyltransferase.

5. Synthesis of frame-shifted farnesyl diphosphate analogs.

6. Simultaneous dual protein labeling using a triorthogonal reagent.

Review 7. A Not-So-Ancient Grease History: Click Chemistry and Protein Lipid Modifications.

8. Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids.