Structural Basis for Control of Methylation Extent in Polyketide Synthase Metal-Dependent C-Methyltr

Lao, Yongtong; Skiba, Meredith A.; Chun, Stephanie W.; Narayan, Alison R.H.; Smith, Janet L.

doi:10.1021/acschembio.2c00085

Structural Basis for Control of Methylation Extent in Polyketide Synthase Metal-Dependent C-Methyltr

Journal Article · 01 May 2022 · ACS Chem. Biol.

DOI:https://doi.org/10.1021/acschembio.2c00085· OSTI ID:1900780

Lao, Yongtong; Skiba, Meredith A.; Chun, Stephanie W.; Narayan, Alison R.H.; Smith, Janet L.

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: DOE - Office Of Science; NIH

OSTI ID:: 1900780

Journal Information:: ACS Chem. Biol., Journal Name: ACS Chem. Biol. Journal Issue: (8) Vol. 17

Country of Publication:: United States

Language:: ENGLISH

References (46)

Installing the “magic methyl” – C–H methylation in synthesis Aynetdinova, Daniya; Callens, Mia C.; Hicks, Harry B. Chemical Society Reviews, Vol. 50, Issue 9 https://doi.org/10.1039/d0cs00973c	journal	January 2021
Structural and Functional Studies of a gem-Dimethylating Methyltransferase from a trans-Acyltransferase Assembly Line Meinke, Jessica L.; Mehaffey, M. Rachel; Wagner, Drew T. ACS Chemical Biology, Vol. 13, Issue 12 https://doi.org/10.1021/acschembio.8b00733	journal	October 2018
Identification of a Saxitoxin Biosynthesis Gene with a History of Frequent Horizontal Gene Transfers Kellmann, Ralf; Michali, Troco Kaan; Neilan, Brett Adam Journal of Molecular Evolution, Vol. 67, Issue 5 https://doi.org/10.1007/s00239-008-9169-2	journal	October 2008
Saxitoxin Thottumkara, Arun P.; Parsons, William H.; Du Bois, J. Angewandte Chemie International Edition, Vol. 53, Issue 23 https://doi.org/10.1002/anie.201308235	journal	April 2014
XDS Kabsch, Wolfgang Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2 https://doi.org/10.1107/s0907444909047337	journal	January 2010
A Mononuclear Iron-Dependent Methyltransferase Catalyzes Initial Steps in Assembly of the Apratoxin A Polyketide Starter Unit Skiba, Meredith A.; Sikkema, Andrew P.; Moss, Nathan A. ACS Chemical Biology, Vol. 12, Issue 12 https://doi.org/10.1021/acschembio.7b00746	journal	November 2017
Jalview Version 2--a multiple sequence alignment editor and analysis workbench Waterhouse, A. M.; Procter, J. B.; Martin, D. M. A. Bioinformatics, Vol. 25, Issue 9 https://doi.org/10.1093/bioinformatics/btp033	journal	January 2009
Biosynthetic Intermediate Analysis and Functional Homology Reveal a Saxitoxin Gene Cluster in Cyanobacteria Kellmann, R.; Mihali, T. K.; Jeon, Y. J. Applied and Environmental Microbiology, Vol. 74, Issue 13 https://doi.org/10.1128/aem.00353-08	journal	May 2008
Domain Organization and Active Site Architecture of a Polyketide Synthase C -methyltransferase Skiba, Meredith A.; Sikkema, Andrew P.; Fiers, William D. ACS Chemical Biology, Vol. 11, Issue 12 https://doi.org/10.1021/acschembio.6b00759	journal	October 2016
The structures of type I polyketide synthases Keatinge-Clay, Adrian T. Natural Product Reports, Vol. 29, Issue 10 https://doi.org/10.1039/c2np20019h	journal	January 2012
Macromolecular structure determination using X-rays, neutrons and electrons: recent developments in Phenix Liebschner, Dorothee; Afonine, Pavel V.; Baker, Matthew L. Acta Crystallographica Section D Structural Biology, Vol. 75, Issue 10 https://doi.org/10.1107/s2059798319011471	journal	October 2019
Methyltransferases excised from trans-AT polyketide synthases operate on N-acetylcysteamine-bound substrates Stevens, D. Cole; Wagner, Drew T.; Manion, Hannah R. The Journal of Antibiotics, Vol. 69, Issue 7 https://doi.org/10.1038/ja.2016.66	journal	June 2016
GNAT-Like Strategy for Polyketide Chain Initiation Gu, L.; Geders, T. W.; Wang, B. Science, Vol. 318, Issue 5852 https://doi.org/10.1126/science.1148790	journal	November 2007
Characterization of Sfp, a Bacillus subtilis Phosphopantetheinyl Transferase for Peptidyl Carrier Protein Domains in Peptide Synthetases ^† Quadri, Luis E. N.; Weinreb, Paul H.; Lei, Ming Biochemistry, Vol. 37, Issue 6 https://doi.org/10.1021/bi9719861	journal	February 1998
Clustal W and Clustal X version 2.0 Larkin, M. A.; Blackshields, G.; Brown, N. P. Bioinformatics, Vol. 23, Issue 21, p. 2947-2948 https://doi.org/10.1093/bioinformatics/btm404	journal	September 2007
Myxovirescin A Biosynthesis is Directed by Hybrid Polyketide Synthases/Nonribosomal Peptide Synthetase, 3-Hydroxy-3-Methylglutaryl-CoA Synthases, and trans-Acting Acyltransferases Simunovic, Vesna; Zapp, Josef; Rachid, Shwan ChemBioChem, Vol. 7, Issue 8 https://doi.org/10.1002/cbic.200600075	journal	July 2006
NMR Spectroscopic Studies on the in Vitro Acyl Glucuronide Migration Kinetics of Ibuprofen ((±)-(R,S)-2-(4-Isobutylphenyl) Propanoic Acid), Its Metabolites, and Analogues Johnson, Caroline H.; Wilson, Ian D.; Harding, John R. Analytical Chemistry, Vol. 79, Issue 22 https://doi.org/10.1021/ac071368i	journal	October 2007
Coot model-building tools for molecular graphics Emsley, Paul; Cowtan, Kevin Acta Crystallographica Section D Biological Crystallography, Vol. 60, Issue 12, p. 2126-2132 https://doi.org/10.1107/s0907444904019158	journal	November 2004
Paralytic shellfish toxin biosynthesis in cyanobacteria and dinoflagellates: A molecular overview Wang, Da-Zhi; Zhang, Shu-Fei; Zhang, Yong Journal of Proteomics, Vol. 135 https://doi.org/10.1016/j.jprot.2015.08.008	journal	March 2016
Neurotoxic Alkaloids: Saxitoxin and Its Analogs Wiese, Maria; D’Agostino, Paul M.; Mihali, Troco K. Marine Drugs, Vol. 8, Issue 7 https://doi.org/10.3390/md8072185	journal	July 2010
Facile Detection of Acyl and Peptidyl Intermediates on Thiotemplate Carrier Domains via Phosphopantetheinyl Elimination Reactions during Tandem Mass Spectrometry ^† Dorrestein, Pieter C.; Bumpus, Stefanie B.; Calderone, Christopher T. Biochemistry, Vol. 45, Issue 42 https://doi.org/10.1021/bi061169d	journal	October 2006
Biocatalytic Detoxification of Paralytic Shellfish Toxins Lukowski, April L.; Denomme, Nicholas; Hinze, Meagan E. ACS Chemical Biology, Vol. 14, Issue 5 https://doi.org/10.1021/acschembio.9b00123	journal	April 2019
Assembly-Line Enzymology for Polyketide and Nonribosomal Peptide Antibiotics: Logic, Machinery, and Mechanisms Fischbach, Michael A.; Walsh, Christopher T. Chemical Reviews, Vol. 106, Issue 8 https://doi.org/10.1021/cr0503097	journal	August 2006
Insertions within the Saxitoxin Biosynthetic Gene Cluster Result in Differential Toxin Profiles Cullen, Alescia; D’Agostino, Paul M.; Mazmouz, Rabia ACS Chemical Biology, Vol. 13, Issue 11 https://doi.org/10.1021/acschembio.8b00608	journal	October 2018
Repurposing the GNAT Fold in the Initiation of Polyketide Biosynthesis Skiba, Meredith A.; Tran, Collin L.; Dan, Qingyun Structure, Vol. 28, Issue 1 https://doi.org/10.1016/j.str.2019.11.004	journal	January 2020
Top-down mass spectrometry on low-resolution instruments: Characterization of phosphopantetheinylated carrier domains in polyketide and non-ribosomal biosynthetic pathways Meluzzi, Dario; Zheng, Wei Hao; Hensler, Mary Bioorganic & Medicinal Chemistry Letters, Vol. 18, Issue 10 https://doi.org/10.1016/j.bmcl.2007.10.104	journal	May 2008
How First Shell–Second Shell Interactions and Metal Substitution Modulate Protein Function Mazmanian, Karine; Dudev, Todor; Lim, Carmay Inorganic Chemistry, Vol. 57, Issue 22 https://doi.org/10.1021/acs.inorgchem.8b01029	journal	June 2018
Profound Methyl Effects in Drug Discovery and a Call for New CH Methylation Reactions Schönherr, Heike; Cernak, Tim Angewandte Chemie International Edition, Vol. 52, Issue 47 https://doi.org/10.1002/anie.201303207	journal	October 2013
Biosynthesis of t -Butyl in Apratoxin A: Functional Analysis and Architecture of a PKS Loading Module Skiba, Meredith A.; Sikkema, Andrew P.; Moss, Nathan A. ACS Chemical Biology, Vol. 13, Issue 6 https://doi.org/10.1021/acschembio.8b00252	journal	April 2018
Ion pairing and reactivity of enolate anions. 5. Thermodynamics of ionization of .beta.-di- and tricarbonyl compounds in dimethyl sulfoxide solution and ion pairing of their alkali salts Arnett, Edward M.; Maroldo, Stephen G.; Schilling, Steven L. Journal of the American Chemical Society, Vol. 106, Issue 22 https://doi.org/10.1021/ja00334a049	journal	October 1984
Biocatalytic Synthesis of α-Amino Ketones Chun, Stephanie W.; Narayan, Alison R. H. Synlett, Vol. 30, Issue 11 https://doi.org/10.1055/s-0037-1611755	journal	March 2019
Chemistry of a Unique Polyketide-like Synthase Chun, Stephanie W.; Hinze, Meagan E.; Skiba, Meredith A. Journal of the American Chemical Society, Vol. 140, Issue 7 https://doi.org/10.1021/jacs.7b13297	journal	February 2018
Synthesis and Identification of Key Biosynthetic Intermediates for the Formation of the Tricyclic Skeleton of Saxitoxin Tsuchiya, Shigeki; Cho, Yuko; Yoshioka, Renpei Angewandte Chemie International Edition, Vol. 56, Issue 19 https://doi.org/10.1002/anie.201612461	journal	March 2017
Chemoenzymatic Total Synthesis of Natural Products Chakrabarty, Suman; Romero, Evan O.; Pyser, Joshua B. Accounts of Chemical Research, Vol. 54, Issue 6 https://doi.org/10.1021/acs.accounts.0c00810	journal	February 2021
Acute oral toxicity and tissue residues of saxitoxin in the mallard (Anas platyrhynchos) Dusek, Robert J.; Smith, Matthew M.; Van Hemert, Caroline Harmful Algae, Vol. 109 https://doi.org/10.1016/j.hal.2021.102109	journal	November 2021
The Role of the Secondary Coordination Sphere in a Fungal Polysaccharide Monooxygenase Span, Elise A.; Suess, Daniel L. M.; Deller, Marc C. ACS Chemical Biology, Vol. 12, Issue 4 https://doi.org/10.1021/acschembio.7b00016	journal	March 2017
MolProbity : all-atom structure validation for macromolecular crystallography Chen, Vincent B.; Arendall, W. Bryan; Headd, Jeffrey J. Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 1 https://doi.org/10.1107/s0907444909042073	journal	December 2009
Structures of human Na _v 1.7 channel in complex with auxiliary subunits and animal toxins Shen, Huaizong; Liu, Dongliang; Wu, Kun Science, Vol. 363, Issue 6433 https://doi.org/10.1126/science.aaw2493	journal	February 2019
A Putative Gene Cluster from a Lyngbya wollei Bloom that Encodes Paralytic Shellfish Toxin Biosynthesis Mihali, Troco K.; Carmichael, Wayne W.; Neilan, Brett A. PLoS ONE, Vol. 6, Issue 2 https://doi.org/10.1371/journal.pone.0014657	journal	February 2011
Saxitoxin, a toxic marine natural product that targets a multitude of receptors Llewellyn, Lyndon E. Natural Product Reports, Vol. 23, Issue 2 https://doi.org/10.1039/b501296c	journal	January 2006
Cloning and characterization of a phosphopantetheinyl transferase from Streptomyces verticillus ATCC15003, the producer of the hybrid peptide–polyketide antitumor drug bleomycin Sánchez, César; Du, Liangcheng; Edwards, Daniel J. Chemistry & Biology, Vol. 8, Issue 7 https://doi.org/10.1016/s1074-5521(01)00047-3	journal	July 2001
Engineered biosynthesis of natural products in heterologous hosts Luo, Yunzi; Li, Bing-Zhi; Liu, Duo Chemical Society Reviews, Vol. 44, Issue 15 https://doi.org/10.1039/c5cs00025d	journal	January 2015
Phaser crystallographic software McCoy, Airlie J.; Grosse-Kunstleve, Ralf W.; Adams, Paul D. Journal of Applied Crystallography, Vol. 40, Issue 4 https://doi.org/10.1107/s0021889807021206	journal	July 2007
New standards for collecting and fitting steady state kinetic data Johnson, Kenneth A. Beilstein Journal of Organic Chemistry, Vol. 15 https://doi.org/10.3762/bjoc.15.2	journal	January 2019
The P1′ specificity of tobacco etch virus protease Kapust, Rachel B.; Tözsér, József; Copeland, Terry D. Biochemical and Biophysical Research Communications, Vol. 294, Issue 5 https://doi.org/10.1016/s0006-291x(02)00574-0	journal	June 2002
The Methylation Effect in Medicinal Chemistry Barreiro, Eliezer J.; Kümmerle, Arthur E.; Fraga, Carlos A. M. Chemical Reviews, Vol. 111, Issue 9 https://doi.org/10.1021/cr200060g	journal	September 2011

Similar Records

Structural Basis of Polyketide Synthase O-Methylation

Journal Article · 2018 · ACS Chemical Biology · OSTI ID:1502222

Substrate Trapping in Polyketide Synthase Thioesterase Domains: Structural Basis for Macrolactone Formation

Journal Article · 2024 · ACS Catalysis · OSTI ID:2581636

Structural Basis for Binding Specificity between Subclasses of Modular Polyketide Synthase Docking Domains

Journal Article · 2009 · ACS Chem. Biol. · OSTI ID:1005509

Structural Basis for Control of Methylation Extent in Polyketide Synthase Metal-Dependent C-Methyltr

Citation Formats

References (46)

Similar Records

Related Subjects