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The structure elucidation and total synthesis of β-lipomycin.
Angew Chem Int Ed Engl. 2014 Jul 07; 53(28):7335-8.AC

Abstract

Here we describe the synthesis of β-lipomycin, a secondary metabolite isolated from the fermentation broth of Corallococcus coralloides. The synthesis relies on the structural assignment made by a statistical method, the so-called profile hidden Markov model. Using this protocol, not only the configuration of the secondary alcohol, but also of the adjacent methyl branch could be deduced. The synthesis therefore not only provides access to this natural product but also confirms the validity of this approach for configurational assignment at methyl branches of modular polyketides.

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Authors+Show Affiliations

Hartmann O
Institute for Organic Chemistry and Centre of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover (Germany); Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig (Germany).
Kalesse M
No affiliation info available

MeSH

Biological ProductsMolecular StructurePolyketidesPyrrolidinones

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24850084

Citation

Hartmann, Olaf, and Markus Kalesse. "The Structure Elucidation and Total Synthesis of Β-lipomycin." Angewandte Chemie (International Ed. in English), vol. 53, no. 28, 2014, pp. 7335-8.
Hartmann O, Kalesse M. The structure elucidation and total synthesis of β-lipomycin. Angew Chem Int Ed Engl. 2014;53(28):7335-8.
Hartmann, O., & Kalesse, M. (2014). The structure elucidation and total synthesis of β-lipomycin. Angewandte Chemie (International Ed. in English), 53(28), 7335-8. https://doi.org/10.1002/anie.201402259
Hartmann O, Kalesse M. The Structure Elucidation and Total Synthesis of Β-lipomycin. Angew Chem Int Ed Engl. 2014 Jul 7;53(28):7335-8. PubMed PMID: 24850084.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The structure elucidation and total synthesis of β-lipomycin. AU - Hartmann,Olaf, AU - Kalesse,Markus, Y1 - 2014/05/21/ PY - 2014/02/12/received PY - 2014/5/23/entrez PY - 2014/5/23/pubmed PY - 2015/10/9/medline KW - lipomycins KW - pentaenes KW - profile hidden Markov model KW - structure elucidation KW - vinylogous Mukaiyama aldol reaction SP - 7335 EP - 8 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 53 IS - 28 N2 - Here we describe the synthesis of β-lipomycin, a secondary metabolite isolated from the fermentation broth of Corallococcus coralloides. The synthesis relies on the structural assignment made by a statistical method, the so-called profile hidden Markov model. Using this protocol, not only the configuration of the secondary alcohol, but also of the adjacent methyl branch could be deduced. The synthesis therefore not only provides access to this natural product but also confirms the validity of this approach for configurational assignment at methyl branches of modular polyketides. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/24850084/The_structure_elucidation_and_total_synthesis_of_β_lipomycin_ DB - PRIME DP - Unbound Medicine ER -