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Metabolic Labeling and Visualization of Isoprenoids Using Alkyne-Modified DMAPP Analogs in Bacillus subtilis.

Λεπτομέρειες βιβλιογραφικής εγγραφής
Τίτλος: Metabolic Labeling and Visualization of Isoprenoids Using Alkyne-Modified DMAPP Analogs in Bacillus subtilis.
Συγγραφείς: Hulsey ZN; Department of Chemistry, University of Tennessee, Knoxville, USA., McBee DP; Department of Chemistry, University of Tennessee, Knoxville, USA., Dolan CL; Department of Chemistry, University of Tennessee, Knoxville, USA., Rossi FM; Department of Chemistry, SUNY Cortland Cortland, New York, USA., Truslow NA; Department of Chemistry, University of Tennessee, Knoxville, USA., Taylor AR; Department of Chemistry, University of Tennessee, Knoxville, USA., Trybala TN; Department of Chemistry, University of Tennessee, Knoxville, USA., Baccile JA; Department of Chemistry, University of Tennessee, Knoxville, USA.
Πηγή: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2026 Aug 24; Vol. 65 (35), pp. e1590156. Date of Electronic Publication: 2026 Jul 10.
Τύπος έκδοσης: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't
Γλώσσα: English
Στοιχεία περιοδικού: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: MEDLINE
Imprint Name(s): Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
Ιατρικοί όροι (MeSH): Bacillus subtilis*/metabolism , Bacillus subtilis*/chemistry , Alkynes*/chemistry , Alkynes*/metabolism , Terpenes*/metabolism , Terpenes*/chemistry , Organophosphorus Compounds*/chemistry , Organophosphorus Compounds*/metabolism , Hemiterpenes*/chemistry , Hemiterpenes*/metabolism
Περίληψη: Isoprenoids are a chemically and functionally diverse class of metabolites that underlie essential bacterial physiology including respiration and cell envelope biogenesis. Chemical interrogation of isoprenoid metabolism remains limited because the two central five-carbon (C5) precursors, isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) are highly polar and cell-impermeant, rendering exogenous addition of them or functional analogs intractable. Here, we report the development of cell-permeant alkynylated DMAPP precursors (1-3) that enable DMAPP-specific bioorthogonal labeling of isoprenoids in Bacillus subtilis. Growth rescue, toxicity profiling, and downstream incorporation analyses showed that alkyne geometry and substitution pattern strongly influence the metabolic suitability of DMAPP surrogates. We found that a directly substituted Z-alkynyl DMAPP analog was the only biosynthetically productive surrogate tested. Metabolic incorporation of this probe resulted in regiospecific labeling of membrane-embedded isoprenoids, including menaquinone-7 (MK-7), bactoprenol, and tetraprenyl-β-curcumene. Pathway inhibition and supplementation assays demonstrate that the labeling efficiency of DMAPP surrogates is governed by competition with endogenous DMAPP and IPP. Lastly, post-incorporation CuAAC derivatization enabled direct visualization of isoprenoid localization and targeted mass-spectrometric profiling of labeled prenyl metabolites. These results establish a general chemical platform for bioorthogonal tagging of C5 metabolism in B. subtilis.
(© 2026 The Author(s). Angewandte Chemie International Edition published by Wiley‐VCH GmbH.)
References: Eur J Biochem. 2002 Jul;269(14):3339-54. (PMID: 12135472)
Nat Rev Mol Cell Biol. 2016 Feb;17(2):110-22. (PMID: 26790532)
Chembiochem. 2009 Dec 14;10(18):2934-43. (PMID: 19856367)
Nat Prod Rep. 2021 Jan 1;38(1):130-239. (PMID: 32935693)
Microbiol Mol Biol Rev. 2005 Dec;69(4):585-607. (PMID: 16339737)
J Am Chem Soc. 2020 Oct 28;142(43):18449-18459. (PMID: 33053303)
Cold Spring Harb Perspect Biol. 2013 Aug 01;5(8):a013359. (PMID: 23751184)
Mol Microbiol. 1999 Mar;31(5):1561-72. (PMID: 10200973)
Chem Rev. 2017 Sep 13;117(17):11570-11648. (PMID: 28841019)
Proc Natl Acad Sci U S A. 2008 May 6;105(18):6725-9. (PMID: 18436644)
J Biol Chem. 2003 May 30;278(22):19898-903. (PMID: 12663672)
Front Microbiol. 2020 May 15;11:914. (PMID: 32499768)
Science. 2007 Apr 6;316(5821):60-1. (PMID: 17412944)
Biochim Biophys Acta. 2000 Dec 15;1529(1-3):33-48. (PMID: 11111076)
Microb Biotechnol. 2022 May;15(5):1633-1651. (PMID: 34856064)
Nat Prod Rep. 2021 May 26;38(5):905-980. (PMID: 33169126)
Mol Biol Evol. 2011 Jan;28(1):87-99. (PMID: 20651049)
Trends Biochem Sci. 2017 Oct;42(10):824-843. (PMID: 28927698)
Chembiochem. 2024 Jun 17;25(12):e202400064. (PMID: 38568158)
Curr Opin Microbiol. 2017 Apr;36:76-84. (PMID: 28237903)
mBio. 2025 Jan 8;16(1):e0302424. (PMID: 39611687)
Plant Commun. 2023 May 8;4(3):100512. (PMID: 36575800)
Org Lett. 2009 Sep 17;11(18):4164-7. (PMID: 19694486)
Chem Rev. 2021 Jun 23;121(12):7178-7248. (PMID: 33821625)
Curr Opin Microbiol. 2023 Aug;74:102315. (PMID: 37058914)
ACS Synth Biol. 2019 Jan 18;8(1):70-81. (PMID: 30543412)
Chembiochem. 2023 Jan 3;24(1):e202200512. (PMID: 36354788)
Cell. 2021 Jun 10;184(12):3109-3124.e22. (PMID: 34004145)
J Am Chem Soc. 2025 Jun 11;147(23):19777-19787. (PMID: 40424498)
Grant Information: 1R35GM157211-01 United States NH NIH HHS; CHE-2204170 National Science Foundation; R35 GM157211 United States GM NIGMS NIH HHS; T32 GM142621 United States GM NIGMS NIH HHS; 1 T32 GM142621 United States NH NIH HHS
Contributed Indexing: Keywords: Bacillus subtilis; biochemistry; biogenesis; bioorthogonal chemistry; chemistry; isopentenyl pyrophosphate; prenylation; pyrophosphate; terpenoid
Substance Nomenclature: 0 (Alkynes)
0 (Terpenes)
0 (Organophosphorus Compounds)
0 (Hemiterpenes)
358-72-5 (3,3-dimethylallyl pyrophosphate)
358-71-4 (isopentenyl pyrophosphate)
Entry Date(s): Date Created: 20260710 Date Completed: 20260824 Latest Revision: 20260916
Update Code: 20260916
PubMed Central ID: PMC13502626
DOI: 10.1002/anie.1590156
PMID: 42429022
Βάση Δεδομένων: MEDLINE
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  Data: Metabolic Labeling and Visualization of Isoprenoids Using Alkyne-Modified DMAPP Analogs in Bacillus subtilis.
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– Name: Abstract
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  Data: Isoprenoids are a chemically and functionally diverse class of metabolites that underlie essential bacterial physiology including respiration and cell envelope biogenesis. Chemical interrogation of isoprenoid metabolism remains limited because the two central five-carbon (C&lt;subscript&gt;5&lt;/subscript&gt;) precursors, isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) are highly polar and cell-impermeant, rendering exogenous addition of them or functional analogs intractable. Here, we report the development of cell-permeant alkynylated DMAPP precursors (1-3) that enable DMAPP-specific bioorthogonal labeling of isoprenoids in Bacillus subtilis. Growth rescue, toxicity profiling, and downstream incorporation analyses showed that alkyne geometry and substitution pattern strongly influence the metabolic suitability of DMAPP surrogates. We found that a directly substituted Z-alkynyl DMAPP analog was the only biosynthetically productive surrogate tested. Metabolic incorporation of this probe resulted in regiospecific labeling of membrane-embedded isoprenoids, including menaquinone-7 (MK-7), bactoprenol, and tetraprenyl-β-curcumene. Pathway inhibition and supplementation assays demonstrate that the labeling efficiency of DMAPP surrogates is governed by competition with endogenous DMAPP and IPP. Lastly, post-incorporation CuAAC derivatization enabled direct visualization of isoprenoid localization and targeted mass-spectrometric profiling of labeled prenyl metabolites. These results establish a general chemical platform for bioorthogonal tagging of C&lt;subscript&gt;5&lt;/subscript&gt; metabolism in B. subtilis.&lt;br /&gt; (&#169; 2026 The Author(s). Angewandte Chemie International Edition published by Wiley‐VCH GmbH.)
– Name: Ref
  Label: References
  Group: RefInfo
  Data: Eur J Biochem. 2002 Jul;269(14):3339-54. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2212135472%22&quot;&gt;12135472)&lt;/searchLink&gt;&lt;br /&gt;Nat Rev Mol Cell Biol. 2016 Feb;17(2):110-22. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2226790532%22&quot;&gt;26790532)&lt;/searchLink&gt;&lt;br /&gt;Chembiochem. 2009 Dec 14;10(18):2934-43. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2219856367%22&quot;&gt;19856367)&lt;/searchLink&gt;&lt;br /&gt;Nat Prod Rep. 2021 Jan 1;38(1):130-239. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2232935693%22&quot;&gt;32935693)&lt;/searchLink&gt;&lt;br /&gt;Microbiol Mol Biol Rev. 2005 Dec;69(4):585-607. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2216339737%22&quot;&gt;16339737)&lt;/searchLink&gt;&lt;br /&gt;J Am Chem Soc. 2020 Oct 28;142(43):18449-18459. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2233053303%22&quot;&gt;33053303)&lt;/searchLink&gt;&lt;br /&gt;Cold Spring Harb Perspect Biol. 2013 Aug 01;5(8):a013359. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2223751184%22&quot;&gt;23751184)&lt;/searchLink&gt;&lt;br /&gt;Mol Microbiol. 1999 Mar;31(5):1561-72. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2210200973%22&quot;&gt;10200973)&lt;/searchLink&gt;&lt;br /&gt;Chem Rev. 2017 Sep 13;117(17):11570-11648. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2228841019%22&quot;&gt;28841019)&lt;/searchLink&gt;&lt;br /&gt;Proc Natl Acad Sci U S A. 2008 May 6;105(18):6725-9. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2218436644%22&quot;&gt;18436644)&lt;/searchLink&gt;&lt;br /&gt;J Biol Chem. 2003 May 30;278(22):19898-903. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2212663672%22&quot;&gt;12663672)&lt;/searchLink&gt;&lt;br /&gt;Front Microbiol. 2020 May 15;11:914. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2232499768%22&quot;&gt;32499768)&lt;/searchLink&gt;&lt;br /&gt;Science. 2007 Apr 6;316(5821):60-1. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2217412944%22&quot;&gt;17412944)&lt;/searchLink&gt;&lt;br /&gt;Biochim Biophys Acta. 2000 Dec 15;1529(1-3):33-48. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2211111076%22&quot;&gt;11111076)&lt;/searchLink&gt;&lt;br /&gt;Microb Biotechnol. 2022 May;15(5):1633-1651. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2234856064%22&quot;&gt;34856064)&lt;/searchLink&gt;&lt;br /&gt;Nat Prod Rep. 2021 May 26;38(5):905-980. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2233169126%22&quot;&gt;33169126)&lt;/searchLink&gt;&lt;br /&gt;Mol Biol Evol. 2011 Jan;28(1):87-99. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2220651049%22&quot;&gt;20651049)&lt;/searchLink&gt;&lt;br /&gt;Trends Biochem Sci. 2017 Oct;42(10):824-843. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2228927698%22&quot;&gt;28927698)&lt;/searchLink&gt;&lt;br /&gt;Chembiochem. 2024 Jun 17;25(12):e202400064. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2238568158%22&quot;&gt;38568158)&lt;/searchLink&gt;&lt;br /&gt;Curr Opin Microbiol. 2017 Apr;36:76-84. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2228237903%22&quot;&gt;28237903)&lt;/searchLink&gt;&lt;br /&gt;mBio. 2025 Jan 8;16(1):e0302424. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2239611687%22&quot;&gt;39611687)&lt;/searchLink&gt;&lt;br /&gt;Plant Commun. 2023 May 8;4(3):100512. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2236575800%22&quot;&gt;36575800)&lt;/searchLink&gt;&lt;br /&gt;Org Lett. 2009 Sep 17;11(18):4164-7. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2219694486%22&quot;&gt;19694486)&lt;/searchLink&gt;&lt;br /&gt;Chem Rev. 2021 Jun 23;121(12):7178-7248. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2233821625%22&quot;&gt;33821625)&lt;/searchLink&gt;&lt;br /&gt;Curr Opin Microbiol. 2023 Aug;74:102315. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2237058914%22&quot;&gt;37058914)&lt;/searchLink&gt;&lt;br /&gt;ACS Synth Biol. 2019 Jan 18;8(1):70-81. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2230543412%22&quot;&gt;30543412)&lt;/searchLink&gt;&lt;br /&gt;Chembiochem. 2023 Jan 3;24(1):e202200512. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2236354788%22&quot;&gt;36354788)&lt;/searchLink&gt;&lt;br /&gt;Cell. 2021 Jun 10;184(12):3109-3124.e22. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2234004145%22&quot;&gt;34004145)&lt;/searchLink&gt;&lt;br /&gt;J Am Chem Soc. 2025 Jun 11;147(23):19777-19787. (PMID: &lt;searchLink fieldCode=&quot;PM&quot; term=&quot;%2240424498%22&quot;&gt;40424498)&lt;/searchLink&gt;
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  Data: 1R35GM157211-01 United States NH NIH HHS; CHE-2204170 National Science Foundation; R35 GM157211 United States GM NIGMS NIH HHS; T32 GM142621 United States GM NIGMS NIH HHS; 1 T32 GM142621 United States NH NIH HHS
– Name: SubjectMinor
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  Data: &lt;i&gt;Keywords: &lt;/i&gt;Bacillus subtilis; biochemistry; biogenesis; bioorthogonal chemistry; chemistry; isopentenyl pyrophosphate; prenylation; pyrophosphate; terpenoid
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  Data: 0 (Alkynes)&lt;br /&gt;0 (Terpenes)&lt;br /&gt;0 (Organophosphorus Compounds)&lt;br /&gt;0 (Hemiterpenes)&lt;br /&gt;358-72-5 (3,3-dimethylallyl pyrophosphate)&lt;br /&gt;358-71-4 (isopentenyl pyrophosphate)
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  Data: 10.1002/anie.1590156
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        Value: 10.1002/anie.1590156
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      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        StartPage: e1590156
    Subjects:
      – SubjectFull: Bacillus subtilis metabolism
        Type: general
      – SubjectFull: Bacillus subtilis chemistry
        Type: general
      – SubjectFull: Alkynes chemistry
        Type: general
      – SubjectFull: Alkynes metabolism
        Type: general
      – SubjectFull: Terpenes metabolism
        Type: general
      – SubjectFull: Terpenes chemistry
        Type: general
      – SubjectFull: Organophosphorus Compounds chemistry
        Type: general
      – SubjectFull: Organophosphorus Compounds metabolism
        Type: general
      – SubjectFull: Hemiterpenes chemistry
        Type: general
      – SubjectFull: Hemiterpenes metabolism
        Type: general
    Titles:
      – TitleFull: Metabolic Labeling and Visualization of Isoprenoids Using Alkyne-Modified DMAPP Analogs in Bacillus subtilis.
        Type: main
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      – PersonEntity:
          Name:
            NameFull: Hulsey ZN
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            NameFull: McBee DP
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            NameFull: Dolan CL
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            NameFull: Truslow NA
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            NameFull: Taylor AR
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            NameFull: Trybala TN
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            NameFull: Baccile JA
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          Dates:
            – D: 24
              M: 08
              Text: 2026 Aug 24
              Type: published
              Y: 2026
          Identifiers:
            – Type: issn-electronic
              Value: 1521-3773
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              Value: 65
            – Type: issue
              Value: 35
          Titles:
            – TitleFull: Angewandte Chemie (International ed. in English)
              Type: main
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