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Literature DB >> 22857735

Synthesis of frame-shifted farnesyl diphosphate analogs.

Andrew T Placzek¹, James L Hougland, Richard A Gibbs.

Abstract

A set of synthetic approaches were developed and applied to the synthesis of eight frame-shifted farnesyl diphosphate (FPP) analogs. These analogs bear increased or decreased methylene units between the double bonds and/or diphosphate moieties of the isoprenoid structure. Evaluation versus mammalian FTase revealed that small structural changes can lead to dramatic changes in substrate ability.

Entities: Chemical Gene Species

Mesh：

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Year: 2012 PMID： 22857735 PMCID： PMC6863160 DOI： 10.1021/ol300683r

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

13 in total

Review 1. The structure and synthesis of the fungal cell wall.

Authors: Shaun M Bowman; Stephen J Free
Journal: Bioessays Date: 2006-08 Impact factor: 4.345

2. Protein farnesyltransferase-catalyzed isoprenoid transfer to peptide depends on lipid size and shape, not hydrophobicity.

Authors: Thangaiah Subramanian; Suxia Liu; Jerry M Troutman; Douglas A Andres; H Peter Spielmann
Journal: Chembiochem Date: 2008-11-24 Impact factor: 3.164

Review 3. Exploration and mining of the bacterial terpenome.

Authors: David E Cane; Haruo Ikeda
Journal: Acc Chem Res Date: 2011-10-31 Impact factor: 22.384

4. Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate.

Authors: Juan A Faraldos; Paul E O'Maille; Nikki Dellas; Joseph P Noel; Robert M Coates
Journal: J Am Chem Soc Date: 2010-03-31 Impact factor: 15.419

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

Authors: Andrew T Placzek; Richard A Gibbs
Journal: Org Lett Date: 2011-06-23 Impact factor: 6.005

6. Production of isoprenoid pharmaceuticals by engineered microbes.

Authors: Michelle C Y Chang; Jay D Keasling
Journal: Nat Chem Biol Date: 2006-12 Impact factor: 15.040

7. Recombinant squalene synthase. A mechanism for the rearrangement of presqualene diphosphate to squalene.

Authors: Brian S J Blagg; Michael B Jarstfer; Daniel H Rogers; C Dale Poulter
Journal: J Am Chem Soc Date: 2002-07-31 Impact factor: 15.419

8. Rho Family GTPase modification and dependence on CAAX motif-signaled posttranslational modification.

Authors: Patrick J Roberts; Natalia Mitin; Patricia J Keller; Emily J Chenette; James P Madigan; Rachel O Currin; Adrienne D Cox; Oswald Wilson; Paul Kirschmeier; Channing J Der
Journal: J Biol Chem Date: 2008-07-09 Impact factor: 5.157

9. Combinatorial modulation of protein prenylation.

Authors: Amanda J Krzysiak; Diwan S Rawat; Sarah A Scott; June E Pais; Misty Handley; Marietta L Harrison; Carol A Fierke; Richard A Gibbs
Journal: ACS Chem Biol Date: 2007-05-25 Impact factor: 5.100

10. Synthesis and biochemical evaluation of 3,7-disubstituted farnesyl diphosphate analogues.

Authors: Diwan S Rawat; Amanda J Krzysiak; Richard A Gibbs
Journal: J Org Chem Date: 2008-01-29 Impact factor: 4.354

5 in total

1. Synthesis of Non-natural, Frame-Shifted Isoprenoid Diphosphate Analogues.

Authors: Kayla J Temple; Elia N Wright; Carol A Fierke; Richard A Gibbs
Journal: Org Lett Date: 2016-11-14 Impact factor: 6.005

2. Exploration of GGTase-I substrate requirements. Part 2: Synthesis and biochemical analysis of novel saturated geranylgeranyl diphosphate analogs.

Authors: Kayla J Temple; Elia N Wright; Carol A Fierke; Richard A Gibbs
Journal: Bioorg Med Chem Lett Date: 2016-06-15 Impact factor: 2.823

3. Farnesyl diphosphate analogues with aryl moieties are efficient alternate substrates for protein farnesyltransferase.

Authors: Thangaiah Subramanian; June E Pais; Suxia Liu; Jerry M Troutman; Yuta Suzuki; Karunai Leela Subramanian; Carol A Fierke; Douglas A Andres; H Peter Spielmann
Journal: Biochemistry Date: 2012-10-02 Impact factor: 3.162

4. Fluorescent probes for investigation of isoprenoid configuration and size discrimination by bactoprenol-utilizing enzymes.

Authors: Anahita Z Mostafavi; Donovan K Lujan; Katelyn M Erickson; Christina D Martinez; Jerry M Troutman
Journal: Bioorg Med Chem Date: 2013-06-15 Impact factor: 3.641

5. Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis.

Authors: Matthew Katcher; Timothy F Jamison
Journal: Tetrahedron Date: 2018-02-02 Impact factor: 2.457

5 in total