Reaction mechanism of the farnesyl pyrophosphate C-methyltransferase towards the biosynthesis of pre-sodorifen pyrophosphate by Serratia plymuthica 4Rx13.
Amino Acid Motifs
Bacterial Proteins
/ chemistry
Binding Sites
Biocatalysis
Bridged Bicyclo Compounds
/ chemistry
Cloning, Molecular
Cyclization
Escherichia coli
/ genetics
Gene Expression
Genetic Vectors
/ chemistry
Methylation
Methyltransferases
/ chemistry
Molecular Docking Simulation
Mutagenesis, Site-Directed
Octanes
/ chemistry
Polyisoprenyl Phosphates
/ chemistry
Protein Binding
Protein Conformation, alpha-Helical
Protein Conformation, beta-Strand
Protein Interaction Domains and Motifs
Recombinant Proteins
/ chemistry
Serratia
/ chemistry
Sesquiterpenes
/ chemistry
Substrate Specificity
Journal
Scientific reports
ISSN: 2045-2322
Titre abrégé: Sci Rep
Pays: England
ID NLM: 101563288
Informations de publication
Date de publication:
04 02 2021
04 02 2021
Historique:
received:
30
10
2020
accepted:
18
01
2021
entrez:
5
2
2021
pubmed:
6
2
2021
medline:
20
11
2021
Statut:
epublish
Résumé
Classical terpenoid biosynthesis involves the cyclization of the linear prenyl pyrophosphate precursors geranyl-, farnesyl-, or geranylgeranyl pyrophosphate (GPP, FPP, GGPP) and their isomers, to produce a huge number of natural compounds. Recently, it was shown for the first time that the biosynthesis of the unique homo-sesquiterpene sodorifen by Serratia plymuthica 4Rx13 involves a methylated and cyclized intermediate as the substrate of the sodorifen synthase. To further support the proposed biosynthetic pathway, we now identified the cyclic prenyl pyrophosphate intermediate pre-sodorifen pyrophosphate (PSPP). Its absolute configuration (6R,7S,9S) was determined by comparison of calculated and experimental CD-spectra of its hydrolysis product and matches with those predicted by semi-empirical quantum calculations of the reaction mechanism. In silico modeling of the reaction mechanism of the FPP C-methyltransferase (FPPMT) revealed a S
Identifiants
pubmed: 33542330
doi: 10.1038/s41598-021-82521-9
pii: 10.1038/s41598-021-82521-9
pmc: PMC7862628
doi:
Substances chimiques
1,2,4,5,6,7,8-heptamethyl-3-methylenebicyclo(3.2.1)oct-6-ene
0
Bacterial Proteins
0
Bridged Bicyclo Compounds
0
Octanes
0
Polyisoprenyl Phosphates
0
Recombinant Proteins
0
Sesquiterpenes
0
geranyl pyrophosphate
763-10-0
farnesyl pyrophosphate
79W6B01D07
Methyltransferases
EC 2.1.1.-
geranylgeranyl pyrophosphate
N21T0D88LX
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
3182Références
Biochemistry. 2012 Apr 10;51(14):3003-10
pubmed: 22455498
J Comput Aided Mol Des. 1995 Jun;9(3):251-68
pubmed: 7561977
Anal Biochem. 1976 May 7;72:248-54
pubmed: 942051
BMC Struct Biol. 2005 Oct 14;5:19
pubmed: 16225687
Curr Opin Biotechnol. 2020 Oct;65:248-258
pubmed: 32679412
Curr Opin Struct Biol. 2002 Dec;12(6):783-93
pubmed: 12504684
Chemistry. 2020 Feb 17;26(10):2178-2182
pubmed: 31898827
Nature. 2004 Nov 4;432(7013):118-22
pubmed: 15525992
Proteins. 2009;77 Suppl 9:114-22
pubmed: 19768677
Nat Chem Biol. 2018 Dec;14(12):1090-1098
pubmed: 30429605
Annu Rev Biophys Biomol Struct. 1995;24:293-318
pubmed: 7663118
Nat Prod Rep. 2012 Oct;29(10):1238-50
pubmed: 22850796
J Chem Inf Model. 2009 Jan;49(1):84-96
pubmed: 19125657
ACS Synth Biol. 2019 Jun 21;8(6):1303-1313
pubmed: 31059642
Trends Biochem Sci. 2003 Jun;28(6):329-35
pubmed: 12826405
Bioinformatics. 2014 Oct 15;30(20):2981-2
pubmed: 24996895
ACS Synth Biol. 2019 Oct 18;8(10):2238-2247
pubmed: 31576747
J Am Chem Soc. 2008 Jul 16;130(28):8908-9
pubmed: 18563898
Proteins. 2003 Sep 1;52(4):609-23
pubmed: 12910460
J Mol Biol. 1995 Mar 17;247(1):16-20
pubmed: 7897657
Chem Biol. 1998 Sep;5(9):R221-33
pubmed: 9751645
J Mol Biol. 1990 Jun 20;213(4):859-83
pubmed: 2359125
J Phys Chem A. 2008 Dec 18;112(50):12868-86
pubmed: 18714947
J Biol Chem. 2012 Jan 6;287(2):1426-34
pubmed: 22117061
Biochem J. 2016 Dec 1;473(23):4385-4397
pubmed: 27613858
J Med Chem. 2007 Feb 22;50(4):726-41
pubmed: 17300160
J Am Chem Soc. 2018 Sep 19;140(37):11855-11862
pubmed: 30133268
J Antibiot (Tokyo). 2008 Oct;61(10):627-32
pubmed: 19168977
Phytochemistry. 2015 May;113:130-9
pubmed: 25596806
Sci Rep. 2017 Apr 13;7(1):862
pubmed: 28408760
Science. 1997 Sep 19;277(5333):1815-20
pubmed: 9295271
Methods Mol Biol. 2014;1153:189-202
pubmed: 24777798
Chem Rev. 2017 Sep 13;117(17):11570-11648
pubmed: 28841019
FEMS Microbiol Lett. 2016 Jul;363(14):
pubmed: 27231241
Cell. 1993 Jul 30;74(2):299-307
pubmed: 8343957
J Biol Chem. 2016 Nov 4;291(45):23403-23415
pubmed: 27573242
Phys Rev A Gen Phys. 1988 Sep 15;38(6):3098-3100
pubmed: 9900728
FEMS Microbiol Lett. 2014 Mar;352(1):45-53
pubmed: 24341572
Proteins. 1993 Dec;17(4):355-62
pubmed: 8108378
Angew Chem Int Ed Engl. 2007;46(43):8287-90
pubmed: 17899580
Angew Chem Int Ed Engl. 2018 May 28;57(22):6629-6632
pubmed: 29603559
Nature. 1990 Feb 1;343(6257):425-30
pubmed: 1967820
Phys Chem Chem Phys. 2005 Sep 21;7(18):3297-305
pubmed: 16240044
J Chem Inf Model. 2012 May 25;52(5):1262-74
pubmed: 22482774
J Mol Model. 2013 Jan;19(1):1-32
pubmed: 23187683
J Biol Chem. 2016 Sep 16;291(38):19962-74
pubmed: 27474738
J Phys Chem A. 2006 Feb 16;110(6):2235-45
pubmed: 16466261
Chembiochem. 2012 Dec 21;13(18):2642-55
pubmed: 23180741
J Comput Chem. 2015 May 15;36(13):996-1007
pubmed: 25824339
Angew Chem Int Ed Engl. 2010 Mar 8;49(11):2009-10
pubmed: 20155769
J Biol Chem. 2014 Dec 5;289(49):33815-25
pubmed: 25288796
Proc Natl Acad Sci U S A. 2008 May 27;105(21):7422-7
pubmed: 18492804
Appl Microbiol Biotechnol. 2010 Oct;88(4):965-76
pubmed: 20717666
Nat Prod Rep. 2011 Jun;28(6):1035-53
pubmed: 21541432
J Am Chem Soc. 2014 Jul 16;136(28):9910-3
pubmed: 24992358
FEMS Microbiol Lett. 2018 Nov 1;365(22):
pubmed: 30307482
Front Microbiol. 2016 May 19;7:737
pubmed: 27242752
PLoS One. 2018 Apr 19;13(4):e0196082
pubmed: 29672609
Nature. 1994 Mar 24;368(6469):354-8
pubmed: 8127373
Chirality. 2013 Apr;25(4):243-9
pubmed: 23532998