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  1. Article: A selective genome-guided method for environmental Burkholderia isolation

    Haeckl, F. P. Jake / João L. Baldim / Dasha Iskakova / Kenji L. Kurita / Marisi G. Soares / Roger G. Linington

    Journal of industrial microbiology & biotechnology. 2019 Mar., v. 46, no. 3-4

    2019  

    Abstract: The genus Burkholderia is an emerging source of novel natural products chemistry, yet to date few methods exist for the selective isolation of strains of this genus from the environment. More broadly, tools to efficiently design selection media for any ... ...

    Abstract The genus Burkholderia is an emerging source of novel natural products chemistry, yet to date few methods exist for the selective isolation of strains of this genus from the environment. More broadly, tools to efficiently design selection media for any given genus would be of significant value to the natural products and microbiology communities. Using a modification of the recently published SMART protocol, we have developed a two-stage isolation protocol for strains from the genus Burkholderia. This method uses a combination of selective agar isolation media and multiplexed PCR profiling to derive Burkholderia strains from environmental samples with 95% efficiency. Creation of this new method paves the way for the systematic exploration of natural products chemistry from this important genus and offers new insight into potential methods for selective isolation method development for other priority genera.
    Keywords Burkholderia ; agar ; culture media ; isolation techniques ; microbiology ; polymerase chain reaction
    Language English
    Dates of publication 2019-03
    Size p. 345-362.
    Publishing place Springer International Publishing
    Document type Article
    ZDB-ID 1482484-X
    ISSN 1476-5535 ; 1367-5435
    ISSN (online) 1476-5535
    ISSN 1367-5435
    DOI 10.1007/s10295-018-02121-x
    Database NAL-Catalogue (AGRICOLA)

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  2. Article: Synthetic Studies Toward the Skyllamycins: Total Synthesis and Generation of Simplified Analogues

    Giltrap, Andrew M / F. P. Jake Haeckl / Kenji L. Kurita / Richard J. Payne / Roger G. Linington

    Journal of organic chemistry. 2018 May 25, v. 83, no. 13

    2018  

    Abstract: Herein, we report our synthetic studies toward the skyllamycins, a highly modified class of nonribosomal peptide natural products which contain a number of interesting structural features, including the extremely rare α-OH-glycine residue. Before ... ...

    Abstract Herein, we report our synthetic studies toward the skyllamycins, a highly modified class of nonribosomal peptide natural products which contain a number of interesting structural features, including the extremely rare α-OH-glycine residue. Before embarking on the synthesis of the natural products, we prepared four structurally simpler analogues. Access to both the analogues and the natural products first required the synthesis of a number of nonproteinogenic amino acids, including three β-OH amino acids that were accessed from the convenient chiral precursor Garner’s aldehyde. Following the preparation of the suitably protected nonproteinogenic amino acids, the skyllamycin analogues were assembled using a solid-phase synthetic route followed by a final stage solution-phase cyclization reaction. To access the natural products (skyllamycins A–C) the synthetic route used for the analogues was modified. Specifically, linear peptide precursors containing a C-terminal amide were synthesized via solid-phase peptide synthesis. After cleavage from the resin the N-terminal serine residue was oxidatively cleaved to a glyoxyamide moiety. The target natural products, skyllamycins A–C, were successfully prepared via a final step cyclization with concomitant formation of the unusual α-OH-glycine residue. Purification and spectroscopic comparison to the authentic isolated material confirmed the identity of the synthetic natural products.
    Keywords aldehydes ; cyclization reactions ; moieties ; organic chemistry ; serine ; spectroscopy
    Language English
    Dates of publication 2018-0525
    Size p. 7250-7270.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.8b00898
    Database NAL-Catalogue (AGRICOLA)

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