Literature DB >> 12475343

Total synthesis of desferrisalmycin B.

Li Dong1, John M Roosenberg, Marvin J Miller.   

Abstract

The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.

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Year:  2002        PMID: 12475343     DOI: 10.1021/ja028386w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  15 in total

1.  Synthesis of Bradyrhizose from d-Glucose.

Authors:  Philemon Ngoje; David Crich
Journal:  Org Lett       Date:  2019-12-26       Impact factor: 6.005

2.  Design and synthesis of a novel protected mixed ligand siderophore.

Authors:  Pingyu Ding; Clara E Schous; Marvin J Miller
Journal:  Tetrahedron Lett       Date:  2008-03-31       Impact factor: 2.415

3.  Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides.

Authors:  David Crich; Abhisek Banerjee
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

Review 4.  Exploiting bacterial iron acquisition: siderophore conjugates.

Authors:  Cheng Ji; Raúl E Juárez-Hernández; Marvin J Miller
Journal:  Future Med Chem       Date:  2012-03       Impact factor: 3.808

5.  Synthesis of (+)-didemniserinolipid B: application of a 2-allyl-4-fluorophenyl auxiliary for relay ring-closing metathesis.

Authors:  Christopher C Marvin; Eric A Voight; Judy M Suh; Christopher L Paradise; Steven D Burke
Journal:  J Org Chem       Date:  2008-09-24       Impact factor: 4.354

6.  Trihydroxamate siderophore-fluoroquinolone conjugates are selective sideromycin antibiotics that target Staphylococcus aureus.

Authors:  Timothy A Wencewicz; Timothy E Long; Ute Möllmann; Marvin J Miller
Journal:  Bioconjug Chem       Date:  2013-02-14       Impact factor: 4.774

Review 7.  Is drug release necessary for antimicrobial activity of siderophore-drug conjugates? Syntheses and biological studies of the naturally occurring salmycin "Trojan Horse" antibiotics and synthetic desferridanoxamine-antibiotic conjugates.

Authors:  Timothy A Wencewicz; Ute Möllmann; Timothy E Long; Marvin J Miller
Journal:  Biometals       Date:  2009-02-17       Impact factor: 2.949

Review 8.  Utilization of microbial iron assimilation processes for the development of new antibiotics and inspiration for the design of new anticancer agents.

Authors:  Marvin J Miller; Helen Zhu; Yanping Xu; Chunrui Wu; Andrew J Walz; Anne Vergne; John M Roosenberg; Garrett Moraski; Albert A Minnick; Julia McKee-Dolence; Jingdan Hu; Kelley Fennell; E Kurt Dolence; Li Dong; Scott Franzblau; Francois Malouin; Ute Möllmann
Journal:  Biometals       Date:  2009-01-07       Impact factor: 2.949

9.  Syntheses of Siderophore-Drug Conjugates Using a Convergent Thiol-Maleimide System.

Authors:  Raúl E Juárez-Hernández; Patricia A Miller; Marvin J Miller
Journal:  ACS Med Chem Lett       Date:  2012-09-04       Impact factor: 4.345

10.  Theranostic Gallium Siderophore Ciprofloxacin Conjugate with Broad Spectrum Antibiotic Potency.

Authors:  Apurva Pandey; Chloé Savino; Shin Hye Ahn; Zhaoyong Yang; Steven G Van Lanen; Eszter Boros
Journal:  J Med Chem       Date:  2019-10-17       Impact factor: 7.446

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