2018
DOI: 10.1002/anie.201808028
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Structure, Total Synthesis, and Biosynthesis of Chloromyxamides: Myxobacterial Tetrapeptides Featuring an Uncommon 6‐Chloromethyl‐5‐methoxypipecolic Acid Building Block

Abstract: Soil-living microbes are an important resource for the discovery of new natural products featuring great structural diversity that are reflective of the underlying biosynthetic pathways as well as incorporating a wide range of intriguing small-molecule building blocks. We report here the full structural elucidation, total synthesis, and biosynthesis of chloromyxamides, a new class of tetrapeptides that display an unprecedented 6-chloromethyl-5-methoxypipecolic acid (CMPA) substructure. Chemical synthesis-inclu… Show more

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Cited by 22 publications
(27 citation statements)
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“…Concerning our ongoing interest into the syntheses of biological active natural products [25][26][27][28][29][30] we also focused on the synthesis of chondramide derivatives 31,32 and we developed a straightforward protocol towards the miuraenamides 33 based on a late stage modification approach. 34 This concept allowed the synthesis of a small library of miuraenamide derivatives via aldol reaction at the C-terminal position of a glycine containing cyclodepsipeptide (Scheme 1).…”
Section: Resultsmentioning
confidence: 99%
“…Concerning our ongoing interest into the syntheses of biological active natural products [25][26][27][28][29][30] we also focused on the synthesis of chondramide derivatives 31,32 and we developed a straightforward protocol towards the miuraenamides 33 based on a late stage modification approach. 34 This concept allowed the synthesis of a small library of miuraenamide derivatives via aldol reaction at the C-terminal position of a glycine containing cyclodepsipeptide (Scheme 1).…”
Section: Resultsmentioning
confidence: 99%
“…S8). 39 This Myxococcus BGC was shown to produce a variety of chlorinated 6-chloromethyl-5-methoxypipecolic acid-containing peptide natural products dubbed chloromyxamides. The chloromyxamide biosynthetic pathway and the role of the BGC-encoded Family 3 encapsulin are currently unknown.…”
Section: Family 3 -Natural Product Encapsulinsmentioning
confidence: 99%
“…Searches were carried out against the UniProt_Trembl database in May 2020 using an E-value cutoff of 10, 0 MSA enrichment iterations in HHblits, and a maximum of 10,000 target hits. 110,112,113 Family 3 encapsulins were identified by searching a previously identified putative encapsulin from Myxococcus (UniProt ID: A0A346D7L6) 39 against the UniProt database using the EFI-EST Sequence BLAST function with an E-value threshold of 1 in February 2021. The resulting datasets generated from these initial searches contained the following numbers of sequences: Family 1: 2,540, Family 2: 3,859, Family 3: 215, Family 4: 95.…”
Section: Genome-mining Searches For Encapsulin-like Systemsmentioning
confidence: 99%
“…1 ) ( Akita et al, 2007 , Giessen et al, 2019 , He et al, 2019 , He et al, 2016 , LaFrance et al, 2021 , Lončar et al, 2020 , McHugh et al, 2014 , Sutter et al, 2008 , Tang et al, 2021 , Wiryaman and Toor, 2021 , Xiong et al, 2020 ). Nevertheless, some researchers have also explored encapsulins from families 2, 3, and 4 ( Clancy Kelley et al, 2007 , Gorges et al, 2018 , Nichols et al, 2020 ). This graphical review will summarize the structural studies of encapsulin nanocompartments, with an emphasis on recent structures released in the last two years.…”
Section: Introductionmentioning
confidence: 99%