Literature DB >> 6434502

Griseochelin, a novel carboxylic acid antibiotic from Streptomyces griseus.

U Gräfe, W Schade, M Roth, L Radics, M Incze, K Ujszászy.   

Abstract

Griseochelin, C33H60O7, isolated from an asporogenous strain of Streptomyces griseus represents a novel carboxylic acid antibiotic. The metabolite, which is active against Gram-positive bacteria, forms water-insoluble salts with mono- and divalent cations and binds alkaline-earth metal ions specifically in 2:1 (X2M) stoichiometry. Detailed spectral (IR, MS and NMR) studies provide full characterization of its constitution featuring a carboxylic acid function, a substituted tetrahydropyran ring, an allylic OH group which are accommodated within a tetrahydroxylated-octamethyl-C25 diene backbone.

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Year:  1984        PMID: 6434502     DOI: 10.7164/antibiotics.37.836

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  7 in total

1.  Evolution of an Efficient and Scalable Nine-Step (Longest Linear Sequence) Synthesis of Zincophorin Methyl Ester.

Authors:  Liang-An Chen; Melissa A Ashley; James L Leighton
Journal:  J Am Chem Soc       Date:  2017-03-15       Impact factor: 15.419

2.  Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin.

Authors:  Zhenlei Song; Richard P Hsung; Ting Lu; Andrew G Lohse
Journal:  J Org Chem       Date:  2007-11-03       Impact factor: 4.354

3.  Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl Ester.

Authors:  Zachary A Kasun; Xin Gao; Radoslaw M Lipinski; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-07-13       Impact factor: 15.419

4.  Toward more "ideal" polyketide natural product synthesis: a step-economical synthesis of zincophorin methyl ester.

Authors:  Tyler J Harrison; Stephen Ho; James L Leighton
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

Review 5.  Challenges in the synthesis of a unique mono-carboxylic acid antibiotic, (+)-zincophorin.

Authors:  Zhenlei Song; Andrew G Lohse; Richard P Hsung
Journal:  Nat Prod Rep       Date:  2009-04       Impact factor: 13.423

6.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419

7.  Tandem silylformylation-crotylsilylation/Tamao oxidation of internal alkynes: a remarkable example of generating complexity from simplicity.

Authors:  Jared T Spletstoser; Michael J Zacuto; James L Leighton
Journal:  Org Lett       Date:  2008-12-18       Impact factor: 6.005

  7 in total

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