Total Synthesis of Tetrahydrolipstatin, Its Derivatives, and Evaluation of Their Ability to Potentia

Khan, Saniya S.; Sudasinghe, Thanuja D.; Landgraf, Alexander D.; Ronning, Donald R.; Sucheck, Steven J.

doi:10.1021/acsinfecdis.1c00283

Total Synthesis of Tetrahydrolipstatin, Its Derivatives, and Evaluation of Their Ability to Potentia

Journal Article · 01 September 2021 · ACS Infect. Dis.

DOI:https://doi.org/10.1021/acsinfecdis.1c00283· OSTI ID:1828039

Khan, Saniya S.; Sudasinghe, Thanuja D.; Landgraf, Alexander D.; Ronning, Donald R.; Sucheck, Steven J.

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: DOE - Office Of Science; National Institutes of Health (NIH)

OSTI ID:: 1828039

Journal Information:: ACS Infect. Dis., Vol. 7, Issue (10)

Country of Publication:: United States

Language:: ENGLISH

References (91)

Drug resistance mechanisms and drug susceptibility testing for tuberculosis No authors listed Respirology https://doi.org/10.1111/resp.13393		September 2018
Mycobacterium tuberculosis : success through dormancy No authors listed FEMS Microbiology Reviews https://doi.org/10.1111/j.1574-6976.2012.00331.x		May 2012
Mycobacterium tuberculosis Antigen 85A and 85C Structures Confirm Binding Orientation and Conserved Substrate Specificity No authors listed Journal of Biological Chemistry https://doi.org/10.1074/jbc.M400811200		June 2004
Role of the Major Antigen of Mycobacterium tuberculosis in Cell Wall Biogenesis No authors listed Science https://doi.org/10.1126/science.276.5317.1420		May 1997
Inactivation of the Mycobacterium tuberculosis Antigen 85 Complex by Covalent, Allosteric Inhibitors No authors listed Journal of Biological Chemistry https://doi.org/10.1074/jbc.M114.582445		July 2014
The Three Mycobacterium tuberculosis Antigen 85 Isoforms Have Unique Substrates and Activities Determined by Non-active Site Regions No authors listed Journal of Biological Chemistry https://doi.org/10.1074/jbc.M114.581579		July 2014
Inactivation of the antigen 85C gene profoundly affects the mycolate content and alters the permeability of the Mycobacterium tuberculosis cell envelope No authors listed Molecular Microbiology https://doi.org/10.1046/j.1365-2958.1999.01310.x		March 1999
Disruption of the Genes Encoding Antigen 85A and Antigen 85B of Mycobacterium tuberculosis H37Rv: Effect on Growth in Culture and in Macrophages No authors listed Infection and Immunity https://doi.org/10.1128/IAI.68.2.767-778.2000		February 2000
Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity. No authors listed The Journal of Antibiotics https://doi.org/10.7164/antibiotics.40.1081		January 1987
Orlistat, a New Lipase Inhibitor for the Management of Obesity No authors listed Pharmacotherapy https://doi.org/10.1592/phco.20.4.270.34882		March 2000
Synthesis of Long‐Chain β‐Lactones and Their Antibacterial Activities against Pathogenic Mycobacteria No authors listed ChemMedChem https://doi.org/10.1002/cmdc.201800720		January 2019
The use of microarray analysis to determine the gene expression profiles of Mycobacterium tuberculosis in response to anti-bacterial compounds No authors listed Tuberculosis https://doi.org/10.1016/j.tube.2003.12.005		January 2004
Mycobacterium tuberculosis Rv3802c Encodes a Phospholipase/Thioesterase and Is Inhibited by the Antimycobacterial Agent Tetrahydrolipstatin No authors listed PLoS ONE https://doi.org/10.1371/journal.pone.0004281		January 2009
Identification and structural characterization of an unusual mycobacterial monomeromycolyl-diacylglycerol: Characterization of a mycobacterial monomeromycolyl-diacylglycerol No authors listed Molecular Microbiology https://doi.org/10.1111/j.1365-2958.2005.04717.x		July 2005
Small-Molecule Probes Reveal Esterases with Persistent Activity in Dormant and Reactivating Mycobacterium tuberculosis No authors listed ACS Infectious Diseases https://doi.org/10.1021/acsinfecdis.6b00135		October 2016
Characterization of Tetrahydrolipstatin and Stereoderivatives on the Inhibition of Essential Mycobacterium tuberculosis Lipid Esterases No authors listed Biochemistry https://doi.org/10.1021/acs.biochem.8b00152		March 2018
The lipase inhibitor tetrahydrolipstatin binds covalently to the putative active site serine of pancreatic lipase No authors listed Journal of Biological Chemistry https://doi.org/10.1016/S0021-9258(18)52203-1		February 1991
Syntheses of Tetrahydrolipstatin and Absolute Configuration of Tetrahydrolipstatin and Lipstatin No authors listed Helvetica Chimica Acta https://doi.org/10.1002/hlca.19870700124		February 1987
A Stereochemical Model for Merged 1,2- and 1,3-Asymmetric Induction in Diastereoselective Mukaiyama Aldol Addition Reactions and Related Processes No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja953901u		January 1996
Stereochemical Structure Activity Relationship Studies (S-SAR) of Tetrahydrolipstatin No authors listed ACS Medicinal Chemistry Letters https://doi.org/10.1021/acsmedchemlett.8b00050		February 2018
An Expeditious Enantioselective Total Synthesis of Valilactone No authors listed The Journal of Organic Chemistry https://doi.org/10.1021/jo060844m		June 2006
Regioselective Carbonylation of trans -Disubstituted Epoxides to β-Lactones: A Viable Entry into syn -Aldol-Type Products No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja405151n		July 2013
Total Synthesis of Tetrahydrolipstatin and Stereoisomers via a Highly Regio- and Diastereoselective Carbonylation of Epoxyhomoallylic Alcohols No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja505639u		July 2014
The Asymmetric Synthesis of Tetrahydrolipstatin No authors listed Asian Journal of Organic Chemistry https://doi.org/10.1002/ajoc.201500240		August 2015
β-Lactams and β-lactones as activity-based probes in chemical biology No authors listed MedChemComm https://doi.org/10.1039/c2md00275b		January 2012
Targeting Lipid Esterases in Mycobacteria Grown Under Different Physiological Conditions Using Activity-based Profiling with Tetrahydrolipstatin (THL) No authors listed Molecular & Cellular Proteomics https://doi.org/10.1074/mcp.M113.029942		December 2013
Immunomodulatory lysophosphatidylserines are regulated by ABHD16A and ABHD12 interplay No authors listed Nature Chemical Biology https://doi.org/10.1038/nchembio.1721		January 2015
Human lysosomal acid lipase inhibitor lalistat impairs Mycobacterium tuberculosis growth by targeting bacterial hydrolases No authors listed MedChemComm https://doi.org/10.1039/C6MD00231E		January 2016
Activity-Based Proteome Profiling of Potential Cellular Targets of Orlistat − An FDA-Approved Drug with Anti-Tumor Activities No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja907716f		December 2009
An Antibacterial β-Lactone Kills Mycobacterium tuberculosis by Disrupting Mycolic Acid Biosynthesis No authors listed Angewandte Chemie International Edition https://doi.org/10.1002/anie.201709365		December 2017
Synthesis and biological investigation of the β-thiolactone and β-lactam analogs of tetrahydrolipstatin No authors listed Organic & Biomolecular Chemistry https://doi.org/10.1039/c2ob06976h		January 2012
Stereoselectivity and Regioselectivity in the Segment-Coupling Prins Cyclization No authors listed The Journal of Organic Chemistry https://doi.org/10.1021/jo010232w		June 2001
A Readily Synthesized and Highly Active Epoxide Carbonylation Catalyst Based on a Chromium Porphyrin Framework: Expanding the Range of Available β-Lactones No authors listed Organic Letters https://doi.org/10.1021/ol036244g		February 2004
Enantiodivergent Synthesis of Both Enantiomers of Sulcatol and Matsutake Alcohol from ( R )-Epichlorohydrin No authors listed Chemistry Letters https://doi.org/10.1246/cl.1987.2017		October 1987
The Intramolecular Asymmetric Pauson−Khand Cyclization as a Novel and General Stereoselective Route to Benzindene Prostacyclins: Synthesis of UT-15 (Treprostinil) No authors listed The Journal of Organic Chemistry https://doi.org/10.1021/jo0347720		February 2004
Vanadium-catalyzed epoxidations. 2. Highly stereoselective epoxidations of acyclic homoallylic alcohols predicted by a detailed transition-state model No authors listed Journal of the American Chemical Society https://doi.org/10.1021/ja00415a067		December 1981
In Situ Generation of the Coates Catalyst: A Practical and Versatile Catalytic System for the Carbonylation of meso -Epoxides No authors listed Organic Letters https://doi.org/10.1021/ol201043d		May 2011
Total synthesis of (-)-tetrahydrolipstatin No authors listed The Journal of Organic Chemistry https://doi.org/10.1021/jo00079a022		December 1993
Diastereoselective allylations and crotylations under phase-transfer conditions using trifluoroborate salts: an application to the total synthesis of (−)-tetrahydrolipstatin No authors listed Tetrahedron Letters https://doi.org/10.1016/j.tetlet.2003.09.053		October 2003
Radical Reaction of Sodium Hypophosphite with Terminal Alkynes: Synthesis of 1,1-Bis- H -phosphinates No authors listed Organic Letters https://doi.org/10.1021/ol052533o		December 2005
Effects of Lipid-Lowering Drugs on Vancomycin Susceptibility of Mycobacteria No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.00872-16		August 2016
To catch a killer. What can mycobacterial models teach us about Mycobacterium tuberculosis pathogenesis? No authors listed Current Opinion in Microbiology https://doi.org/10.1016/j.mib.2009.11.006		February 2010
Genome-wide Phenotypic Profiling Identifies and Categorizes Genes Required for Mycobacterial Low Iron Fitness No authors listed Scientific Reports https://doi.org/10.1038/s41598-019-47905-y		August 2019
High-Resolution Phenotypic Profiling Defines Genes Essential for Mycobacterial Growth and Cholesterol Catabolism No authors listed PLoS Pathogens https://doi.org/10.1371/journal.ppat.1002251		September 2011
Global Assessment of Genomic Regions Required for Growth in Mycobacterium tuberculosis No authors listed PLoS Pathogens https://doi.org/10.1371/journal.ppat.1002946		September 2012
Characterization of Two New Multidrug-Resistant Strains of Mycobacterium smegmatis: Tools for Routine In Vitro Screening of Novel Anti-Mycobacterial Agents No authors listed Antibiotics https://doi.org/10.3390/antibiotics8010004		January 2019
Rel Is Required for Morphogenesis of Resting Cells in Mycobacterium smegmatis No authors listed Frontiers in Microbiology https://doi.org/10.3389/fmicb.2016.01390		August 2016
Features of the biochemistry of Mycobacterium smegmatis, as a possible model for Mycobacterium tuberculosis No authors listed Journal of Infection and Public Health https://doi.org/10.1016/j.jiph.2020.06.023		September 2020
Resazurin reduction assays for screening of anti-tubercular compounds against dormant and actively growing Mycobacterium tuberculosis, Mycobacterium bovis BCG and Mycobacterium smegmatis No authors listed Journal of Antimicrobial Chemotherapy https://doi.org/10.1093/jac/dkm207		June 2007
Laboratory Maintenance of Mycobacterium smegmatis No authors listed Current Protocols in Microbiology https://doi.org/10.1002/9780471729259.mc10c01s14		August 2009
Mycobacterium tuberculosis Strains H37ra and H37rv have equivalent minimum inhibitory concentrations to most antituberculosis drugs No authors listed International Journal of Mycobacteriology https://doi.org/10.4103/ijmy.ijmy_33_18		January 2018
Genetic Basis of Virulence Attenuation Revealed by Comparative Genomic Analysis of Mycobacterium tuberculosis Strain H37Ra versus H37Rv No authors listed PLoS ONE https://doi.org/10.1371/journal.pone.0002375		June 2008
Comparative proteomic analysis of Mycobacterium tuberculosis strain H37Rv versus H37Ra No authors listed International Journal of Mycobacteriology https://doi.org/10.1016/j.ijmyco.2013.10.004		December 2013
Determination of in vitro synergy between linezolid and other antimicrobial agents against Mycobacterium tuberculosis isolates No authors listed Tuberculosis https://doi.org/10.1016/j.tube.2015.07.003		December 2015
Multidrug Resistance of a Porin Deletion Mutant of Mycobacterium smegmatis No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.48.11.4163-4170.2004		November 2004
Genetic characterization of mycobacterial l,d-transpeptidases No authors listed Microbiology https://doi.org/10.1099/mic.0.078980-0		August 2014
Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis? No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.39.12.2620		December 1995
Efflux Pump-Mediated Intrinsic Drug Resistance in Mycobacterium smegmatis No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.48.7.2415-2423.2004		July 2004
The Discovery of 2-Aminobenzimidazoles That Sensitize Mycobacterium smegmatis and M. tuberculosis to β-Lactam Antibiotics in a Pattern Distinct from β-Lactamase Inhibitors No authors listed Angewandte Chemie International Edition https://doi.org/10.1002/anie.201612006		March 2017
Synergistic Drug Combinations for Tuberculosis Therapy Identified by a Novel High-Throughput Screen No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.00474-11		May 2011
A rapid and non-pathogenic assay for association of Mycobacterium tuberculosis gyrBA mutations and fluoroquinolone resistance using recombinant Mycobacterium smegmatis No authors listed FEMS Microbiology Letters https://doi.org/10.1093/femsle/fny266		November 2018
Increased Vancomycin Susceptibility in Mycobacteria: a New Approach To Identify Synergistic Activity against Multidrug-Resistant Mycobacteria No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.04856-14		June 2015
Use of Mycobacterium smegmatis Deficient in ADP-Ribosyltransferase as Surrogate for Mycobacterium tuberculosis in Drug Testing and Mutation Analysis No authors listed PLOS ONE https://doi.org/10.1371/journal.pone.0122076		April 2015
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.41.5.1004		May 1997
Molecular Basis of Intrinsic Macrolide Resistance in the Mycobacterium tuberculosis Complex No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.48.1.143-150.2004		January 2004
Rifampin- or Capreomycin-Induced Remodeling of the Mycobacterium smegmatis Mycolic Acid Layer Is Mitigated in Synergistic Combinations with Cationic Antimicrobial Peptides No authors listed mSphere https://doi.org/10.1128/mSphere.00218-18		August 2018
AsnB Is Involved in Natural Resistance of Mycobacterium smegmatis to Multiple Drugs No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.50.1.250-255.2006		January 2006
Molecular basis of clarithromycin activity against Mycobacterium avium and Mycobacterium smegmatis No authors listed Journal of Antimicrobial Chemotherapy https://doi.org/10.1093/jac/41.2.179		February 1998
Reproducibility of the microdilution checkerboard method for antibiotic synergy No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.37.3.613		March 1993
Combination approaches to combat multidrug-resistant bacteria No authors listed Trends in Biotechnology https://doi.org/10.1016/j.tibtech.2012.12.006		March 2013
Requirement of the mymA Operon for Appropriate Cell Wall Ultrastructure and Persistence of Mycobacterium tuberculosis in the Spleens of Guinea Pigs No authors listed Journal of Bacteriology https://doi.org/10.1128/JB.187.12.4173-4186.2005		June 2005
Drug-Resistant Tuberculosis 2020: Where We Stand No authors listed Applied Sciences https://doi.org/10.3390/app10062153		March 2020
Characterization of tetracycline resistance mediated by the efflux pump Tap from Mycobacterium fortuitum No authors listed Journal of Antimicrobial Chemotherapy https://doi.org/10.1093/jac/dki436		February 2006
Antimicrobial resistance in Mycobacterium tuberculosis: mechanistic and evolutionary perspectives No authors listed FEMS Microbiology Reviews https://doi.org/10.1093/femsre/fux011		March 2017
New Insights in to the Intrinsic and Acquired Drug Resistance Mechanisms in Mycobacteria No authors listed Frontiers in Microbiology https://doi.org/10.3389/fmicb.2017.00681		April 2017
Potency of vancomycin against Mycobacterium tuberculosis in the hollow fiber system model No authors listed Journal of Global Antimicrobial Resistance https://doi.org/10.1016/j.jgar.2021.01.005		March 2021
Bacterial resistance to antibiotics: Enzymatic degradation and modification No authors listed Advanced Drug Delivery Reviews https://doi.org/10.1016/j.addr.2005.04.002		July 2005
Recent updates on drug resistance in Mycobacterium tuberculosis No authors listed Journal of Applied Microbiology https://doi.org/10.1111/jam.14478		October 2019
Look and Outlook on Enzyme-Mediated Macrolide Resistance No authors listed Frontiers in Microbiology https://doi.org/10.3389/fmicb.2018.01942		August 2018
Inactivation of fusidic acid by resistant Streptomyces strains. No authors listed The Journal of Antibiotics https://doi.org/10.7164/antibiotics.44.785		January 1991
Purification and properties of the Mycobacterium smegmatis mc2155 β-lactamase No authors listed FEMS Microbiology Letters https://doi.org/10.1016/S0378-1097(97)00041-4		April 1997
Genetic analysis of the β-lactamases of Mycobacterium tuberculosis and Mycobacterium smegmatis and susceptibility to β-lactam antibiotics No authors listed Microbiology https://doi.org/10.1099/mic.0.27629-0		February 2005
Inactivation of Mycobacterium tuberculosis l,d-Transpeptidase Ldt _Mt1 by Carbapenems and Cephalosporins No authors listed Antimicrobial Agents and Chemotherapy https://doi.org/10.1128/AAC.00665-12		May 2012
Fluorometric substrate for sulfatase and lipase No authors listed Analytical Chemistry https://doi.org/10.1021/ac50159a034		December 1969
Phaser crystallographic software No authors listed Journal of Applied Crystallography https://doi.org/10.1107/S0021889807021206		July 2007
Fast detection of drug interaction in Mycobacterium tuberculosis by a checkerboard resazurin method No authors listed Tuberculosis https://doi.org/10.1016/j.tube.2013.09.001		November 2013
Mechanism of inhibition of Mycobacterium tuberculosis antigen 85 by ebselen No authors listed Nature Communications https://doi.org/10.1038/ncomms3748		November 2013
DIALS : implementation and evaluation of a new integration package No authors listed Acta Crystallographica Section D Structural Biology https://doi.org/10.1107/S2059798317017235		February 2018
PHENIX: a comprehensive Python-based system for macromolecular structure solution No authors listed Acta Crystallographica Section D Biological Crystallography https://doi.org/10.1107/S0907444909052925		January 2010
electronic Ligand Builder and Optimization Workbench ( eLBOW ): a tool for ligand coordinate and restraint generation No authors listed Acta Crystallographica Section D Biological Crystallography https://doi.org/10.1107/S0907444909029436		September 2009
Features and development of Coot No authors listed Acta Crystallographica Section D Biological Crystallography https://doi.org/10.1107/S0907444910007493		March 2010

Similar Records

Total Synthesis of Tetrahydrolipstatin, Its Derivatives, and Evaluation of Their Ability to Potentia

Journal Article · 2021 · ACS Infect. Dis. · OSTI ID:1828936

Khan, Saniya S.; Sudasinghe, Thanuja D.; Landgraf, Alexander D.; +2 more

Total synthesis benzene and its derivatives as major gasoline extenders

Journal Article · 1976 · Science; (United States) · OSTI ID:7313979

Tamers, M A

Growth of SJL/J-derived transplantable reticulum cell sarcoma as related to its ability to induce T-cell proliferation in the host- III. Studies on thymectomized and congenitally athymic SJL mice. [Mice]

Journal Article · 1981 · Cell. Immunol.; (United States) · OSTI ID:5549371

Katz, I R; Chapman-Alexander, J; Jacobson, E B; +2 more

Total Synthesis of Tetrahydrolipstatin, Its Derivatives, and Evaluation of Their Ability to Potentia

Citation Formats

References (91)

Similar Records

Related Subjects