Literature DB >> 20801036

A general scheme for synthesis of substrate-based polyketide labels for acyl carrier proteins.

Erick K Leggans1, David L Akey, Janet L Smith, Robert A Fecik.   

Abstract

A general strategy to enzymatically label acyl carrier proteins (ACPs) of polyketide synthases has been developed. Incorporation of a chloromethyl ketone or vinyl ketone moiety into polyketide chain elongation intermediate mimics allows for the synthesis of CoA adducts. These CoA adducts undergo enzymatic reaction with Sfp, a phosphopantetheinyl transferase, to afford labeled CurB carrier proteins.
Copyright © 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20801036      PMCID： PMC2992964          DOI： 10.1016/j.bmcl.2010.05.089

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  32 in total

1.  Crystal structure of the macrocycle-forming thioesterase domain of the erythromycin polyketide synthase: versatility from a unique substrate channel.

Authors:  S C Tsai; L J Miercke; J Krucinski; R Gokhale; J C Chen; P G Foster; D E Cane; C Khosla; R M Stroud
Journal:  Proc Natl Acad Sci U S A       Date:  2001-12-18       Impact factor: 11.205

2.  The structure of docking domains in modular polyketide synthases.

Authors:  R William Broadhurst; Daniel Nietlispach; Michael P Wheatcroft; Peter F Leadlay; Kira J Weissman
Journal:  Chem Biol       Date:  2003-08

3.  Manipulation of carrier proteins in antibiotic biosynthesis.

Authors:  James J La Clair; Timothy L Foley; Tracy R Schegg; Conor M Regan; Michael D Burkart
Journal:  Chem Biol       Date:  2004-02

4.  A new enzyme superfamily - the phosphopantetheinyl transferases.

Authors:  R H Lambalot; A M Gehring; R S Flugel; P Zuber; M LaCelle; M A Marahiel; R Reid; C Khosla; C T Walsh
Journal:  Chem Biol       Date:  1996-11

Review 5.  Genetic approaches to polyketide antibiotics. 1.

Authors:  Robert McDaniel; Mark Welch; C Richard Hutchinson
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

6.  A method for trapping intermediates of polyketide biosynthesis with a nonhydrolyzable malonyl-coenzyme A analogue.

Authors:  Dieter Spiteller; Claire L Waterman; Jonathan B Spencer
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-04       Impact factor: 15.336

7.  Direct acylation of carrier proteins with functionalized beta-lactones.

Authors:  Jon W Amoroso; Lawrence S Borketey; Gitanjeli Prasad; Nathan A Schnarr
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

8.  Aminoacyl-CoAs as probes of condensation domain selectivity in nonribosomal peptide synthesis.

Authors:  P J Belshaw; C T Walsh; T Stachelhaus
Journal:  Science       Date:  1999-04-16       Impact factor: 47.728

9.  The structure of a ketoreductase determines the organization of the beta-carbon processing enzymes of modular polyketide synthases.

Authors:  Adrian T Keatinge-Clay; Robert M Stroud
Journal:  Structure       Date:  2006-03-23       Impact factor: 5.006

10.  Spontaneous alpha-N-6-phosphogluconoylation of a "His tag" in Escherichia coli: the cause of extra mass of 258 or 178 Da in fusion proteins.

Authors:  K F Geoghegan; H B Dixon; P J Rosner; L R Hoth; A J Lanzetti; K A Borzilleri; E S Marr; L H Pezzullo; L B Martin; P K LeMotte; A S McColl; A V Kamath; J G Stroh
Journal:  Anal Biochem       Date:  1999-02-01       Impact factor: 3.365
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  2 in total

1.  Generating enzyme and radical-mediated bisubstrates as tools for investigating Gcn5-related N-acetyltransferases.

Authors:  Cory Reidl; Karolina A Majorek; Joseph Dang; David Tran; Kristen Jew; Melissa Law; Yasmine Payne; Wladek Minor; Daniel P Becker; Misty L Kuhn
Journal:  FEBS Lett       Date:  2017-08-01       Impact factor: 4.124

2.  Polyketide intermediate mimics as probes for revealing cryptic stereochemistry of ketoreductase domains.

Authors:  Yang Li; William D Fiers; Steffen M Bernard; Janet L Smith; Courtney C Aldrich; Robert A Fecik
Journal:  ACS Chem Biol       Date:  2014-11-05       Impact factor: 5.100
  2 in total

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