Literature DB >> 26356680

A Highly Stereoselective and Scalable Synthesis of L-allo-Enduracididine.

William Craig1, Janet Chen1, David Richardson1, Rondel Thorpe1, Yu Yuan1.   

Abstract

A highly stereoselective and scalable synthesis of L-allo-enduracididine from hydroxyproline derivative is described. Pyrrolidine oxidation and reductive ring opening are the key steps in the synthesis. Compared to previously reported approaches, the current route affords l-allo-enduracididine in 10 steps from 3 in 31% overall yield with >50:1 diastereoselectivity.

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Year:  2015        PMID： 26356680     DOI： 10.1021/acs.orglett.5b02362

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


  9 in total

1.  Characterization of a Citrulline 4-Hydroxylase from Nonribosomal Peptide GE81112 Biosynthesis and Engineering of Its Substrate Specificity for the Chemoenzymatic Synthesis of Enduracididine.

Authors:  Christian R Zwick; Max B Sosa; Hans Renata
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-11       Impact factor: 15.336

2.  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

3.  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 4.  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

5.  Evaluation of 3-Borono-l-Phenylalanine as a Water-Soluble Boron Neutron Capture Therapy Agent.

Authors:  Naoya Kondo; Fuko Hirano; Takashi Temma
Journal:  Pharmaceutics       Date:  2022-05-22       Impact factor: 6.525

6.  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

Review 7.  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

8.  Lysine Scanning of Arg10-Teixobactin: Deciphering the Role of Hydrophobic and Hydrophilic Residues.

Authors:  Shimaa A H Abdel Monaim; Yahya E Jad; Estelle J Ramchuran; Ayman El-Faham; Thavendran Govender; Hendrik G Kruger; Beatriz G de la Torre; Fernando Albericio
Journal:  ACS Omega       Date:  2016-12-19

9.  Gram-scale total synthesis of teixobactin promoting binding mode study and discovery of more potent antibiotics.

Authors:  Yu Zong; Fang Fang; Kirsten J Meyer; Liguo Wang; Zhihao Ni; Hongying Gao; Kim Lewis; Jingren Zhang; Yu Rao
Journal:  Nat Commun       Date:  2019-07-22       Impact factor: 14.919
  9 in total

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