Structure Elucidation, Total Synthesis, Antibacterial In Vivo Efficacy and Biosynthesis Proposal of Myxobacterial Corramycin.
Antibiotics
Biosynthesis
Corramycin
Myxobacteria
Natural Products
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
19 12 2022
19 12 2022
Historique:
received:
21
07
2022
pubmed:
6
10
2022
medline:
15
12
2022
entrez:
5
10
2022
Statut:
ppublish
Résumé
Herein, we describe the myxobacterial natural product Corramycin isolated from Corallococcus coralloides. The linear peptide structure contains an unprecedented (2R,3S)-γ-N-methyl-β-hydroxy-histidine moiety. Corramycin exhibits anti-Gram-negative activity against Escherichia coli (E. coli) and is taken up via two transporter systems, SbmA and YejABEF. Furthermore, the Corramycin biosynthetic gene cluster (BGC) was identified and a biosynthesis model was proposed involving a 12-modular non-ribosomal peptide synthetase/polyketide synthase. Bioinformatic analysis of the BGC combined with the development of a total synthesis route allowed for the elucidation of the molecule's absolute configuration. Importantly, intravenous administration of 20 mg kg
Identifiants
pubmed: 36197755
doi: 10.1002/anie.202210747
pmc: PMC10099666
doi:
Substances chimiques
Anti-Bacterial Agents
0
Polyketide Synthases
79956-01-7
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202210747Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
Science. 2015 Jun 5;348(6239):1106-12
pubmed: 26045430
Nat Chem Biol. 2009 Mar;5(3):166-73
pubmed: 19182784
Anal Biochem. 2009 Mar 15;386(2):244-50
pubmed: 19135023
J Antibiot (Tokyo). 2014 Jan;67(1):7-22
pubmed: 23756684
Angew Chem Int Ed Engl. 2018 Jul 9;57(28):8754-8759
pubmed: 29694699
J Microbiol Biotechnol. 2020 Jul 28;30(7):982-995
pubmed: 32347079
ACS Chem Biol. 2018 Nov 16;13(11):3123-3130
pubmed: 30286293
PLoS Genet. 2016 Jun 29;12(6):e1006124
pubmed: 27355376
Nature. 2019 Dec;576(7787):459-464
pubmed: 31747680
BMC Evol Biol. 2007 May 16;7:78
pubmed: 17506888
J Nat Prod. 2016 Mar 25;79(3):629-61
pubmed: 26852623
Chem Sci. 2021 Aug 12;12(35):11882-11893
pubmed: 34659729
Antimicrob Agents Chemother. 2013 Nov;57(11):5548-58
pubmed: 23979750
Clin Infect Dis. 2020 Feb 3;70(4):704-709
pubmed: 31328228
Angew Chem Int Ed Engl. 2012 Jan 16;51(3):811-6
pubmed: 22162209
Angew Chem Int Ed Engl. 2023 Jan 9;62(2):e202214094
pubmed: 36308277
Nat Biotechnol. 2003 May;21(5):526-31
pubmed: 12692562
Nat Prod Rep. 2001 Aug;18(4):380-416
pubmed: 11548049
Proc Natl Acad Sci U S A. 2014 Jun 24;111(25):9259-64
pubmed: 24927540
Int J Antimicrob Agents. 2010 Apr;35(4):333-7
pubmed: 20071153
Nature. 2004 Mar 25;428(6981):441-5
pubmed: 15042094
Nat Biotechnol. 2007 Apr;25(4):447-53
pubmed: 17369815
Chem Biol. 1999 Aug;6(8):493-505
pubmed: 10421756
Chem Biol. 2002 Jan;9(1):103-12
pubmed: 11841943
PLoS One. 2014 Nov 04;9(11):e111904
pubmed: 25369527
Nature. 2019 Dec;576(7787):452-458
pubmed: 31645764
Microbiology (Reading). 2005 May;151(Pt 5):1507-1523
pubmed: 15870461
J Bacteriol. 2007 Nov;189(22):8361-5
pubmed: 17873039
J Pept Sci. 2009 Dec;15(12):799-807
pubmed: 19827002
Nature. 2021 May;593(7857):125-129
pubmed: 33854236
J Bacteriol. 1995 Jun;177(11):3323-5
pubmed: 7768835
Science. 2016 May 13;352(6287):758-61
pubmed: 27174968
Nat Chem Biol. 2015 Sep;11(9):660-70
pubmed: 26284673
Nucleic Acids Res. 2011 Jul;39(Web Server issue):W362-7
pubmed: 21558170
Future Microbiol. 2018 Dec;13:1693-1696
pubmed: 30526061
Proc Natl Acad Sci U S A. 2006 Oct 10;103(41):15200-5
pubmed: 17015832
Proc Natl Acad Sci U S A. 2019 Oct 22;116(43):21748-21757
pubmed: 31591200
Science. 2009 Aug 28;325(5944):1089-93
pubmed: 19713519
J Bacteriol. 2013 Dec;195(23):5352-61
pubmed: 24078611
Antibiotics (Basel). 2016 May 24;5(2):
pubmed: 27231947