Literature DB >> 24848452

Total synthesis of a reported fluorometabolite from Streptomyces sp. TC1 indicates an incorrect assignment. The isolated compound did not contain fluorine.

Mohammed Salah Ayoup1, David B Cordes, Alexandra M Z Slawin, David O'Hagan.   

Abstract

3,5-Di-tert-butyl-4-fluorophenylpropionic acid (1) was recently reported as a natural product from Streptomyces sp. TC1. This was a notable disclosure because fluorinated natural products are exceedingly rare, and in this case it suggested that the bacterium had the capacity to mediate an enzymatic aryl fluorination reaction. However, a synthesis of the putative metabolite 1 demonstrates that the spectroscopic data are inconsistent with the proposed structure. There is no evidence that the isolated compound contained a fluorine atom.

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Year:  2014        PMID: 24848452     DOI: 10.1021/np500260z

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  3 in total

Review 1.  The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research.

Authors:  James B McAlpine; Shao-Nong Chen; Andrei Kutateladze; John B MacMillan; Giovanni Appendino; Andersson Barison; Mehdi A Beniddir; Maique W Biavatti; Stefan Bluml; Asmaa Boufridi; Mark S Butler; Robert J Capon; Young H Choi; David Coppage; Phillip Crews; Michael T Crimmins; Marie Csete; Pradeep Dewapriya; Joseph M Egan; Mary J Garson; Grégory Genta-Jouve; William H Gerwick; Harald Gross; Mary Kay Harper; Precilia Hermanto; James M Hook; Luke Hunter; Damien Jeannerat; Nai-Yun Ji; Tyler A Johnson; David G I Kingston; Hiroyuki Koshino; Hsiau-Wei Lee; Guy Lewin; Jie Li; Roger G Linington; Miaomiao Liu; Kerry L McPhail; Tadeusz F Molinski; Bradley S Moore; Joo-Won Nam; Ram P Neupane; Matthias Niemitz; Jean-Marc Nuzillard; Nicholas H Oberlies; Fernanda M M Ocampos; Guohui Pan; Ronald J Quinn; D Sai Reddy; Jean-Hugues Renault; José Rivera-Chávez; Wolfgang Robien; Carla M Saunders; Thomas J Schmidt; Christoph Seger; Ben Shen; Christoph Steinbeck; Hermann Stuppner; Sonja Sturm; Orazio Taglialatela-Scafati; Dean J Tantillo; Robert Verpoorte; Bin-Gui Wang; Craig M Williams; Philip G Williams; Julien Wist; Jian-Min Yue; Chen Zhang; Zhengren Xu; Charlotte Simmler; David C Lankin; Jonathan Bisson; Guido F Pauli
Journal:  Nat Prod Rep       Date:  2018-07-13       Impact factor: 13.423

2.  Defluorodearomatization: A Photocatalytic Birch-Like Reduction That Enables C-C Bond Formation and Provides Access to Unnatural Cannabinoids.

Authors:  Jon I Day; Sascha Grotjahn; Sameera Senaweera; Burkhard Koenig; Jimmie D Weaver Iii
Journal:  J Org Chem       Date:  2021-06-02       Impact factor: 4.354

3.  Identification of a fluorometabolite from Streptomyces sp. MA37: (2R3S4S)-5-fluoro-2,3,4-trihydroxypentanoic acid.

Authors:  Long Ma; Axel Bartholome; Ming Him Tong; Zhiwei Qin; Yi Yu; Thomas Shepherd; Kwaku Kyeremeh; Hai Deng; David O'Hagan
Journal:  Chem Sci       Date:  2014-12-03       Impact factor: 9.825

  3 in total

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