Literature DB >> 32017574

MS-Derived Isotopic Fine Structure Reveals Forazoline A as a Thioketone-Containing Marine-Derived Natural Product.

Fan Zhang1, Thomas P Wyche2, Yanlong Zhu3,4, Doug R Braun1, Jia-Xuan Yan1, Shaurya Chanana1, Ying Ge3,4,5, Ilia A Guzei5, Marc G Chevrette6,7, Cameron R Currie7, Michael G Thomas7, Scott R Rajski1, Tim S Bugni1.   

Abstract

Forazoline A is a structurally complex PKS-NRPS hybrid produced by marine-derived Actinomadura sp. During the course of studies highlighting the application of IFS analysis as a powerful tool for natural products analysis, we were alerted to an earlier misinterpretation with respect to forazoline A structure elucidation. In particular, IFS reveals that forazoline A contains a thioketone moiety rarely seen in secondary metabolites and, thus, constitutes an even more intriguing structure than originally thought.

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Year:  2020        PMID： 32017574      PMCID： PMC7494057          DOI： 10.1021/acs.orglett.9b04535

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


  17 in total

1.  In vitro characterization of the enzymes involved in TDP-D-forosamine biosynthesis in the spinosyn pathway of Saccharopolyspora spinosa.

Authors:  Lin Hong; Zongbao Zhao; Charles E Melançon; Hua Zhang; Hung-wen Liu
Journal:  J Am Chem Soc       Date:  2008-03-18       Impact factor: 15.419

2.  Enzymatic Thioamide Formation in a Bacterial Antimetabolite Pathway.

Authors:  Agnieszka Litomska; Keishi Ishida; Kyle L Dunbar; Marco Boettger; Sébastien Coyne; Christian Hertweck
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-02       Impact factor: 15.336

3.  Enzymatic reconstitution of ribosomal peptide backbone thioamidation.

Authors:  Nilkamal Mahanta; Andi Liu; Shihui Dong; Satish K Nair; Douglas A Mitchell
Journal:  Proc Natl Acad Sci U S A       Date:  2018-03-05       Impact factor: 11.205

4.  Insights into the thioamidation of thiopeptins to enhance the understanding of the biosynthetic logic of thioamide-containing thiopeptides.

Authors:  Jingyu Liu; Zhi Lin; Yuqing Li; Qingfei Zheng; Dandan Chen; Wen Liu
Journal:  Org Biomol Chem       Date:  2019-04-10       Impact factor: 3.876

5.  High-resolution direct infusion-based mass spectrometry in combination with whole 13C metabolome isotope labeling allows unambiguous assignment of chemical sum formulas.

Authors:  Patrick Giavalisco; Jan Hummel; Jan Lisec; Alvaro Cuadros Inostroza; Gareth Catchpole; Lothar Willmitzer
Journal:  Anal Chem       Date:  2008-12-15       Impact factor: 6.986

6.  Basis Set Requirements for Sulfur Compounds in Density Functional Theory:  a Comparison between Correlation-Consistent, Polarized-Consistent, and Pople-Type Basis Sets.

Authors:  Pablo A Denis
Journal:  J Chem Theory Comput       Date:  2005-09       Impact factor: 6.006

7.  Forazoline A: marine-derived polyketide with antifungal in vivo efficacy.

Authors:  Thomas P Wyche; Jeff S Piotrowski; Yanpeng Hou; Doug Braun; Raamesh Deshpande; Sean McIlwain; Irene M Ong; Chad L Myers; Ilia A Guzei; William M Westler; David R Andes; Tim S Bugni
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

8.  Advances in structure elucidation of small molecules using mass spectrometry.

Authors:  Tobias Kind; Oliver Fiehn
Journal:  Bioanal Rev       Date:  2010-08-21

9.  Seven Golden Rules for heuristic filtering of molecular formulas obtained by accurate mass spectrometry.

Authors:  Tobias Kind; Oliver Fiehn
Journal:  BMC Bioinformatics       Date:  2007-03-27       Impact factor: 3.169

10.  Reconstitution of Iterative Thioamidation in Closthioamide Biosynthesis Reveals Tailoring Strategy for Nonribosomal Peptide Backbones.

Authors:  Kyle L Dunbar; Maria Dell; Evelyn M Molloy; Florian Kloss; Christian Hertweck
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-07       Impact factor: 15.336
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  3 in total

1.  General Method for the Synthesis of α- or β-Deoxyaminoglycosides Bearing Basic Nitrogen.

Authors:  Kevin M Hoang; Nicholas R Lees; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2021-02-08       Impact factor: 15.419

2.  Bacillibactins E and F from a Marine Sponge-Associated Bacillus sp.

Authors:  Qihao Wu; Kurt Throckmorton; Mitasree Maity; Marc G Chevrette; Doug R Braun; Scott R Rajski; Cameron R Currie; Michael G Thomas; Tim S Bugni
Journal:  J Nat Prod       Date:  2020-12-18       Impact factor: 4.050

Review 3.  A look around the West Indies: The spices of life are secondary metabolites.

Authors:  Adrian Demeritte; William M Wuest
Journal:  Bioorg Med Chem       Date:  2020-10-01       Impact factor: 3.641
  3 in total

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