Literature DB >> 26654835

Synthesis and Biological Evaluation of a Teixobactin Analogue.

Yahya E Jad, Gerardo A Acosta1,2, Tricia Naicker, Melissa Ramtahal, Ayman El-Faham3,4, Thavendran Govender, Hendrik G Kruger, Beatriz G de la Torre, Fernando Albericio1,2,4,5.   

Abstract

The first synthesis and biological activity of a teixobactin analogue is reported. Substitution of the unusual L-allo-enduracididine residue by the naturally occurring L-arginine was achieved, and the analogue gave an activity trend similar to that of teixobactin (against Gram-postive bacteria) and meropenem, which was approved by the FDA in 1996. The synthetic route used allows for the synthesis of the natural product as well as the development of a program of medicinal chemistry.

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Year:  2015        PMID: 26654835     DOI: 10.1021/acs.orglett.5b03176

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


  19 in total

1.  X-ray crystallographic structure of a teixobactin analogue reveals key interactions of the teixobactin pharmacophore.

Authors:  H Yang; D R Du Bois; J W Ziller; J S Nowick
Journal:  Chem Commun (Camb)       Date:  2017-02-28       Impact factor: 6.222

2.  Elucidation of the Teixobactin Pharmacophore.

Authors:  Hyunjun Yang; Kevin H Chen; James S Nowick
Journal:  ACS Chem Biol       Date:  2016-06-03       Impact factor: 5.100

Review 3.  Recent Progress in Natural-Product-Inspired Programs Aimed To Address Antibiotic Resistance and Tolerance.

Authors:  Yasmeen Abouelhassan; Aaron T Garrison; Hongfen Yang; Alejandra Chávez-Riveros; Gena M Burch; Robert W Huigens
Journal:  J Med Chem       Date:  2019-04-18       Impact factor: 7.446

4.  Escaping mechanisms of ESKAPE pathogens from antibiotics and their targeting by natural compounds.

Authors:  Ragi Jadimurthy; Shilpa Borehalli Mayegowda; S Chandra Nayak; Chakrabhavi Dhananjaya Mohan; Kanchugarakoppal S Rangappa
Journal:  Biotechnol Rep (Amst)       Date:  2022-04-04

5.  De Novo Resistance to Arg10-Teixobactin Occurs Slowly and Is Costly.

Authors:  Daniel G Lloyd; Benjamin J Schofield; Matthew R Goddard; Edward J Taylor
Journal:  Antimicrob Agents Chemother       Date:  2020-12-16       Impact factor: 5.191

6.  Solid-Phase Synthesis of Megamolecules.

Authors:  Blaise R Kimmel; Justin A Modica; Kelly Parker; Vinayak Dravid; Milan Mrksich
Journal:  J Am Chem Soc       Date:  2020-03-03       Impact factor: 15.419

7.  Synthetic Natural Product Inspired Cyclic Peptides.

Authors:  Matthew A Hostetler; Chloe Smith; Samantha Nelson; Zachary Budimir; Ramya Modi; Ian Woolsey; Autumn Frerk; Braden Baker; Jessica Gantt; Elizabeth I Parkinson
Journal:  ACS Chem Biol       Date:  2021-10-26       Impact factor: 5.100

8.  Total synthesis of teixobactin.

Authors:  Kang Jin; Iek Hou Sam; Kathy Hiu Laam Po; Du'an Lin; Ebrahim H Ghazvini Zadeh; Sheng Chen; Yu Yuan; Xuechen Li
Journal:  Nat Commun       Date:  2016-08-03       Impact factor: 14.919

9.  Binding Modes of Teixobactin to Lipid II: Molecular Dynamics Study.

Authors:  Yang Liu; Yaxin Liu; Mary B Chan-Park; Yuguang Mu
Journal:  Sci Rep       Date:  2017-12-08       Impact factor: 4.379

Review 10.  Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis.

Authors:  Darcy J Atkinson; Briar J Naysmith; Daniel P Furkert; Margaret A Brimble
Journal:  Beilstein J Org Chem       Date:  2016-11-07       Impact factor: 2.883

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