Chemically Induced Cell Wall Stapling in Bacteria.
antibiotic
bacteria
cell wall
click chemistry
cross-linking
d-amino acid
metabolic labeling
peptidoglycan
transpeptidase
Journal
Cell chemical biology
ISSN: 2451-9448
Titre abrégé: Cell Chem Biol
Pays: United States
ID NLM: 101676030
Informations de publication
Date de publication:
18 02 2021
18 02 2021
Historique:
received:
28
05
2020
revised:
09
09
2020
accepted:
06
11
2020
pubmed:
26
11
2020
medline:
3
9
2021
entrez:
25
11
2020
Statut:
ppublish
Résumé
Transpeptidation reinforces the structure of cell-wall peptidoglycan, an extracellular heteropolymer that protects bacteria from osmotic lysis. The clinical success of transpeptidase-inhibiting β-lactam antibiotics illustrates the essentiality of these cross-linkages for cell-wall integrity, but the presence of multiple, seemingly redundant transpeptidases in many species makes it challenging to determine cross-link function. Here, we present a technique to link peptide strands by chemical rather than enzymatic reaction. We employ biocompatible click chemistry to induce triazole formation between azido- and alkynyl-d-alanine residues that are metabolically installed in the peptidoglycan of Gram-positive or Gram-negative bacteria. Synthetic triazole cross-links can be visualized using azidocoumarin-d-alanine, an amino acid derivative that undergoes fluorescent enhancement upon reaction with terminal alkynes. Cell-wall stapling protects Escherichia coli from treatment with the broad-spectrum β-lactams ampicillin and carbenicillin. Chemical control of cell-wall structure in live bacteria can provide functional insights that are orthogonal to those obtained by genetics.
Identifiants
pubmed: 33238158
pii: S2451-9456(20)30435-9
doi: 10.1016/j.chembiol.2020.11.006
pmc: PMC7897265
mid: NIHMS1646766
pii:
doi:
Substances chimiques
Anti-Bacterial Agents
0
Cross-Linking Reagents
0
Peptides
0
beta-Lactams
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
213-220.e4Subventions
Organisme : NIGMS NIH HHS
ID : R25 GM086264
Pays : United States
Organisme : NIGMS NIH HHS
ID : T32 GM120007
Pays : United States
Informations de copyright
Copyright © 2020 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Interests The authors declare no competing interests. The authors have a patent related to this work. Siegrist MS, Jewett JC, Shieh P, Gordon CG, Bertozzi CR. 2016. “D-amino acid derivative-modified peptidoglycan and methods of use thereof.” U.S. patent 9,303,068.
Références
Nature. 1970 Jul 11;227(5254):138-40
pubmed: 4393335
J Am Chem Soc. 2013 Mar 6;135(9):3311-4
pubmed: 23421439
Elife. 2018 Sep 10;7:
pubmed: 30198841
J Bacteriol. 1991 Jun;173(11):3425-31
pubmed: 2045364
J Bacteriol. 1988 Mar;170(3):1373-6
pubmed: 2893787
Antimicrob Agents Chemother. 1991 Sep;35(9):1824-8
pubmed: 1952852
Science. 1957 Jan 18;125(3238):99-101
pubmed: 13390969
J Mol Biol. 1969 May 14;41(3):419-29
pubmed: 4896021
Cell. 2010 May 28;141(5):822-33
pubmed: 20510929
Cell. 2014 Dec 4;159(6):1300-11
pubmed: 25480295
Biochemistry. 2017 Jul 25;56(29):3710-3724
pubmed: 28666084
Biophys J. 2014 Sep 2;107(5):1082-1089
pubmed: 25185544
Chem Asian J. 2011 Oct 4;6(10):2796-802
pubmed: 21905231
J Bacteriol. 1997 May;179(9):2823-34
pubmed: 9139895
J Am Chem Soc. 2020 Jun 24;142(25):10910-10913
pubmed: 32510943
Annu Rev Biochem. 2018 Jun 20;87:991-1014
pubmed: 29596002
EMBO J. 2011 Jul 26;30(16):3442-53
pubmed: 21792174
J Bacteriol. 1985 Jan;161(1):238-42
pubmed: 3881387
Nature. 2014 Feb 27;506(7489):507-10
pubmed: 24336210
J Bacteriol. 2019 Jun 21;201(14):
pubmed: 31036730
FEMS Microbiol Lett. 2011 May;318(1):1-9
pubmed: 21276045
Science. 2009 Sep 18;325(5947):1552-5
pubmed: 19762646
FEMS Microbiol Rev. 2015 Mar;39(2):184-202
pubmed: 25725012
Infect Immun. 2011 Sep;79(9):3596-606
pubmed: 21768286
Nat Commun. 2014 Sep 19;5:4981
pubmed: 25236616
J Bacteriol. 1980 Dec;144(3):1009-16
pubmed: 6777363
J Bacteriol. 1944 Oct;48(4):393-9
pubmed: 16560845
J Infect Dis. 2011 Sep 1;204(5):731-40
pubmed: 21844299
J Bacteriol. 1987 Nov;169(11):5308-10
pubmed: 3312172
Chem Commun (Camb). 2017 Feb 7;53(11):1896-1899
pubmed: 28116363
Proc Natl Acad Sci U S A. 2008 Dec 9;105(49):19282-7
pubmed: 19050072
Philos Trans R Soc Lond B Biol Sci. 2015 Oct 5;370(1679):
pubmed: 26370943
FEMS Microbiol Rev. 2008 Mar;32(2):149-67
pubmed: 18194336
J Bacteriol. 1999 Jul;181(13):3981-93
pubmed: 10383966
Proc Natl Acad Sci U S A. 1975 Oct;72(10):4162-6
pubmed: 674
Biochim Biophys Acta. 2008 Sep;1778(9):1714-34
pubmed: 17658458
Crit Rev Biochem Mol Biol. 2017 Oct;52(5):503-542
pubmed: 28644060
Proc Natl Acad Sci U S A. 2007 Jan 16;104(3):997-1002
pubmed: 17215377
J Bacteriol. 2019 Mar 13;201(7):
pubmed: 30642990
Proc Natl Acad Sci U S A. 1975 Aug;72(8):2999-3003
pubmed: 1103132
ACS Chem Biol. 2013 Mar 15;8(3):500-5
pubmed: 23240806
Proc Natl Acad Sci U S A. 2018 Apr 17;115(16):4069-4074
pubmed: 29610312
J Bacteriol. 1992 Sep;174(17):5549-59
pubmed: 1512190
Nature. 2014 Sep 18;513(7518):418-21
pubmed: 25043002
Trends Microbiol. 2010 Feb;18(2):59-66
pubmed: 20060721
J Biol Chem. 1988 Jul 25;263(21):10088-95
pubmed: 3292521
Angew Chem Int Ed Engl. 2012 Dec 7;51(50):12519-23
pubmed: 23055266
J Gen Microbiol. 1986 May;132(5):1297-304
pubmed: 3534137
Angew Chem Int Ed Engl. 2015 May 18;54(21):6158-62
pubmed: 25832713
Org Lett. 2004 Nov 25;6(24):4603-6
pubmed: 15548086