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Hill, Robert A.; Sutherland, Andrew

doi:10.1039/c4np90007c

Nat. Prod. Rep.

2014

DOI: 10.1039/c4np90007c

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Robert A. Hill

Andrew Sutherland

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Cited by 4 publications

(1 citation statement)

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“…TC1 . The isolation immediately attracted attention because the identification of fluorine-containing metabolites is extremely rare. , Also this would be a particularly intriguing compound, as it suggests that the microorganism has an enzyme that can accomplish an aryl fluorination, a class of enzyme reaction without precedent. Such an enzyme would have exciting biotechnological potential in view of the large-scale utility of aryl fluorides in the fine chemicals industry.…”

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confidence: 99%

Total Synthesis of a Reported Fluorometabolite from Streptomyces sp. TC1 Indicates an Incorrect Assignment. The Isolated Compound Did Not Contain Fluorine

et al. 2014

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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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confidence: 99%

Total Synthesis of a Reported Fluorometabolite from Streptomyces sp. TC1 Indicates an Incorrect Assignment. The Isolated Compound Did Not Contain Fluorine

et al. 2014

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Design of Selenium‐Based Chiral Chemical Probes for Simultaneous Enantio‐ and Chemosensing of Chiral Carboxylic Acids with Remote Stereogenic Centers by NMR Spectroscopy

Shyshkanov

Orlov

2016

Chemistry A European J

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Selenium-based enantiopure chiral chemical probes have been designed in a modular way starting from available amino alcohols. The probes developed were found to be efficient in chemoselective interaction with carboxylic functions of chiral substrates leading to diastereomeric amide formation and in sensing α-, β-, and remote (up to seven bonds away from the carboxylic group) chiral centers by using Se NMR spectroscopy. As a result, it was possible to determine the enantiomeric ratio of structurally diverse individual chiral acids including polyfunctional compounds and drugs with high accuracy. An approach to analyzing the crude reaction mixtures has been successfully developed by using bifunctional selenium- and fluorine-containing chiral probes. More importantly, it was revealed that, based on the Se NMR data obtained, it is possible to obtain primary information about the location and nature of the substituents at the chiral center (chemo- and enantiosensing), which can simplify the structural elucidation of complex compounds. The derivatization procedure takes as little as 5 min and can be performed directly in an NMR tube followed by NMR measurements without any isolation and purification steps.

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The discovery, complex crystal structure, and recognition mechanism of a novel natural PDE4 inhibitor from Selaginella pulvinata

Huang

Liu

et al. 2017

Biochemical Pharmacology

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Hot off the press

Cited by 4 publications

References 32 publications

Total Synthesis of a Reported Fluorometabolite from Streptomyces sp. TC1 Indicates an Incorrect Assignment. The Isolated Compound Did Not Contain Fluorine

Total Synthesis of a Reported Fluorometabolite from Streptomyces sp. TC1 Indicates an Incorrect Assignment. The Isolated Compound Did Not Contain Fluorine

Design of Selenium‐Based Chiral Chemical Probes for Simultaneous Enantio‐ and Chemosensing of Chiral Carboxylic Acids with Remote Stereogenic Centers by NMR Spectroscopy

The discovery, complex crystal structure, and recognition mechanism of a novel natural PDE4 inhibitor from Selaginella pulvinata

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