Literature DB >> 27934359

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

Kayla J Temple1, Elia N Wright2, Carol A Fierke2, Richard A Gibbs1.   

Abstract

A set of synthetic approaches was developed and applied to the synthesis of eight frame-shifted isoprenoid diphosphate analogues. These analogues were designed to increase or decrease the methylene units between the double bonds and/or the pyrophosphate moieties of the isoprenoid structure. Evaluation of mammalian GGTase-I and FTase revealed that small structural changes can result in substantial changes in substrate activity.

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Year:  2016        PMID： 27934359      PMCID： PMC6020017          DOI： 10.1021/acs.orglett.6b02977

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


  18 in total

1.  Evaluation of protein farnesyltransferase substrate specificity using synthetic peptide libraries.

Authors:  Amanda J Krzysiak; Sarah A Scott; Katherine A Hicks; Carol A Fierke; Richard A Gibbs
Journal:  Bioorg Med Chem Lett       Date:  2007-08-16       Impact factor: 2.823

2.  Synthesis of desthio prenylcysteine analogs: sulfur is important for biological activity.

Authors:  Brian S Henriksen; Jessica L Anderson; Christine A Hrycyna; Richard A Gibbs
Journal:  Bioorg Med Chem Lett       Date:  2005-09-23       Impact factor: 2.823

3.  Exploration of GGTase-I substrate requirements. Part 1: Synthesis and biochemical evaluation of novel aryl-modified geranylgeranyl diphosphate analogs.

Authors:  Kayla J Temple; Elia N Wright; Carol A Fierke; Richard A Gibbs
Journal:  Bioorg Med Chem Lett       Date:  2016-06-16       Impact factor: 2.823

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

Authors:  Mohammad Rashidian; James M Song; Rachel E Pricer; Mark D Distefano
Journal:  J Am Chem Soc       Date:  2012-05-08       Impact factor: 15.419

Review 5.  Terpene biosynthesis: modularity rules.

Authors:  Eric Oldfield; Fu-Yang Lin
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-21       Impact factor: 15.336

6.  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

7.  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

8.  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

9.  6- and 14-Fluoro farnesyl diphosphate: mechanistic probes for the reaction catalysed by aristolochene synthase.

Authors:  David J Miller; Fanglei Yu; David W Knight; Rudolf K Allemann
Journal:  Org Biomol Chem       Date:  2009-01-20       Impact factor: 3.876

10.  High-throughput screening for terpene-synthase-cyclization activity and directed evolution of a terpene synthase.

Authors:  Ryan Lauchli; Kersten S Rabe; Karolina Z Kalbarczyk; Amulya Tata; Thomas Heel; Rebekah Z Kitto; Frances H Arnold
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-26       Impact factor: 15.336
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