Literature DB >> 23521145

Mutasynthesis of fluorinated pactamycin analogues and their antimalarial activity.

Khaled H Almabruk1, Wanli Lu, Yuexin Li, Mostafa Abugreen, Jane X Kelly, Taifo Mahmud.   

Abstract

A mutasynthetic strategy has been used to generate fluorinated TM-025 and TM-026, two biosynthetically engineered pactamycin analogues produced by Streptomyces pactum ATCC 27456. The fluorinated compounds maintain excellent activity and selectivity toward chloroquine-sensitive and multidrug-resistant strains of malarial parasites as the parent compounds. The results also provide insights into the biosynthesis of 3-aminobenzoic acid in S. pactum.

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Year:  2013        PMID： 23521145      PMCID： PMC3663920          DOI： 10.1021/ol4004614

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


  14 in total

1.  Biosynthetic studies and genetic engineering of pactamycin analogs with improved selectivity toward malarial parasites.

Authors:  Wanli Lu; Niran Roongsawang; Taifo Mahmud
Journal:  Chem Biol       Date:  2011-04-22

2.  Dissecting the ribosomal inhibition mechanisms of edeine and pactamycin: the universally conserved residues G693 and C795 regulate P-site RNA binding.

Authors:  George Dinos; Daniel N Wilson; Yoshika Teraoka; Witold Szaflarski; Paola Fucini; Dimitrios Kalpaxis; Knud H Nierhaus
Journal:  Mol Cell       Date:  2004-01-16       Impact factor: 17.970

3.  Promising lead compounds for novel antiprotozoals.

Authors:  Kazuhiko Otoguro; Masato Iwatsuki; Aki Ishiyama; Miyuki Namatame; Aki Nishihara-Tukashima; Seiji Shibahara; Shinichi Kondo; Haruki Yamada; Satoshi Omura
Journal:  J Antibiot (Tokyo)       Date:  2010-05-26       Impact factor: 2.649

4.  The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit.

Authors:  D E Brodersen; W M Clemons; A P Carter; R J Morgan-Warren; B T Wimberly; V Ramakrishnan
Journal:  Cell       Date:  2000-12-22       Impact factor: 41.582

5.  Total synthesis of pactamycin.

Authors:  Stephen Hanessian; Ramkrishna Reddy Vakiti; Stéphane Dorich; Shyamapada Banerjee; Fabien Lecomte; Juan R DelValle; Jianbin Zhang; Benoît Deschênes-Simard
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-02       Impact factor: 15.336

Review 6.  The rare fluorinated natural products and biotechnological prospects for fluorine enzymology.

Authors:  K K Jason Chan; David O'Hagan
Journal:  Methods Enzymol       Date:  2012       Impact factor: 1.600

7.  Effect of pactamycin on synthesis of poliovirus proteins: a method for genetic mapping.

Authors:  R Taber; D Rekosh; D Baltimore
Journal:  J Virol       Date:  1971-10       Impact factor: 5.103

8.  Diastereocontrolled construction of pactamycin's complex ureido triol functional array.

Authors:  Justin T Malinowski; Stefan J McCarver; Jeffrey S Johnson
Journal:  Org Lett       Date:  2012-05-22       Impact factor: 6.005

9.  Synthesis of the oxygenated pactamycin core.

Authors:  Spencer Knapp; Younong Yu
Journal:  Org Lett       Date:  2007-03-06       Impact factor: 6.005

10.  Deciphering pactamycin biosynthesis and engineered production of new pactamycin analogues.

Authors:  Takuya Ito; Niran Roongsawang; Norifumi Shirasaka; Wanli Lu; Patricia M Flatt; Noer Kasanah; Cristobal Miranda; Taifo Mahmud
Journal:  Chembiochem       Date:  2009-09-04       Impact factor: 3.164
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  18 in total

1.  Fixing the Unfixable: The Art of Optimizing Natural Products for Human Medicine.

Authors:  Audrey E Yñigez-Gutierrez; Brian O Bachmann
Journal:  J Med Chem       Date:  2019-04-26       Impact factor: 7.446

Review 2.  The secondary metabolite pactamycin with potential for pharmaceutical applications: biosynthesis and regulation.

Authors:  Auday A Eida; Taifo Mahmud
Journal:  Appl Microbiol Biotechnol       Date:  2019-04-25       Impact factor: 4.813

3.  Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.

Authors:  Nels C Gerstner; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2019-10-16       Impact factor: 4.354

4.  Preparation and biological evaluation of synthetic and polymer-encapsulated congeners of the antitumor agent pactamycin: insight into functional group effects and biological activity.

Authors:  Robert J Sharpe; Justin T Malinowski; Federico Sorana; J Christopher Luft; Charles J Bowerman; Joseph M DeSimone; Jeffrey S Johnson
Journal:  Bioorg Med Chem       Date:  2015-02-21       Impact factor: 3.641

5.  Global and pathway-specific transcriptional regulations of pactamycin biosynthesis in Streptomyces pactum.

Authors:  Wanli Lu; Abdullah R Alanzi; Mostafa E Abugrain; Takuya Ito; Taifo Mahmud
Journal:  Appl Microbiol Biotechnol       Date:  2018-10-01       Impact factor: 4.813

6.  Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.

Authors:  Nels C Gerstner; Christopher S Adams; R David Grigg; Maik Tretbar; Jared W Rigoli; Jennifer M Schomaker
Journal:  Org Lett       Date:  2016-01-07       Impact factor: 6.005

Review 7.  Microbial genome mining for accelerated natural products discovery: is a renaissance in the making?

Authors:  Brian O Bachmann; Steven G Van Lanen; Richard H Baltz
Journal:  J Ind Microbiol Biotechnol       Date:  2013-12-17       Impact factor: 3.346

Review 8.  Strategies for the Syntheses of Pactamycin and Jogyamycin.

Authors:  Nels C Gerstner; Kate A Nicastri; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-18       Impact factor: 15.336

9.  Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.

Authors:  Josephine Eshon; Nels C Gerstner; Jennifer M Schomaker
Journal:  ARKIVOC       Date:  2018-11-26       Impact factor: 1.140

10.  Asymmetric synthesis of the aminocyclitol pactamycin, a universal translocation inhibitor.

Authors:  Robert J Sharpe; Justin T Malinowski; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2013-11-18       Impact factor: 15.419
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