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MedKoo Cat#: 526449 | Name: Thiolactomycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Thiolactomycin is a novel reversible dual inhibitor of D-Aspartate oxidase (DDO) and D-amino acid oxidase (DAO).

Chemical Structure

Thiolactomycin
Thiolactomycin
CAS#82079-32-1

Theoretical Analysis

MedKoo Cat#: 526449

Name: Thiolactomycin

CAS#: 82079-32-1

Chemical Formula: C11H14O2S

Exact Mass: 210.0700

Molecular Weight: 210.29

Elemental Analysis: C, 62.83; H, 6.71; O, 15.22; S, 15.25

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Synonym
Thiolactomycin
IUPAC/Chemical Name
(2R)-5-Hydroxy-2,4-dimethyl-2-[(1E)-2-methylbuta-1,3-dienyl]thiophen-3-one
InChi Key
HGCGJTZCWZFGBT-XUIVZRPNSA-N
InChi Code
InChI=1S/C11H14O2S/c1-5-7(2)6-11(4)9(12)8(3)10(13)14-11/h5-6,13H,1H2,2-4H3/b7-6+/t11-/m1/s1
SMILES Code
O=C1[C@](/C=C(C)/C=C)(C)SC(O)=C1C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 210.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Durairaj DR, Shanmughavel P. In Silico Drug Design of Thiolactomycin Derivatives Against Mtb-KasA Enzyme to Inhibit Multidrug Resistance of Mycobacterium tuberculosis. Interdiscip Sci. 2017 Aug 30. doi: 10.1007/s12539-017-0257-0. [Epub ahead of print] PubMed PMID: 28856604. 2: Li J, Tang X, Awakawa T, Moore BS. Enzymatic C-H Oxidation-Amidation Cascade in the Production of Natural and Unnatural Thiotetronate Antibiotics with Potentiated Bioactivity. Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12234-12239. doi: 10.1002/anie.201705239. Epub 2017 Sep 1. PubMed PMID: 28833969; PubMed Central PMCID: PMC5673260. 3: Tang X, Li J, Moore BS. Minimization of the Thiolactomycin Biosynthetic Pathway Reveals that the Cytochrome P450 Enzyme TlmF Is Required for Five-Membered Thiolactone Ring Formation. Chembiochem. 2017 Jun 19;18(12):1072-1076. doi: 10.1002/cbic.201700090. Epub 2017 May 11. PubMed PMID: 28393452; PubMed Central PMCID: PMC5574029. 4: Yurkovich ME, Jenkins R, Sun Y, Tosin M, Leadlay PF. The polyketide backbone of thiolactomycin is assembled by an unusual iterative polyketide synthase. Chem Commun (Camb). 2017 Feb 9;53(13):2182-2185. doi: 10.1039/c6cc09934c. PubMed PMID: 28124037. 5: Balaji NV, Hari Babu B, Subbaraju GV, Purna Nagasree K, Murali Krishna Kumar M. Synthesis, screening and docking analysis of hispolon analogs as potential antitubercular agents. Bioorg Med Chem Lett. 2017 Jan 1;27(1):11-15. doi: 10.1016/j.bmcl.2016.11.047. Epub 2016 Nov 18. PubMed PMID: 27894872. 6: Ward MS, Silva I, Martinez W, Jefferson J, Rahman S, Garcia JM, Kanichar D, Roppiyakuda L, Kosmowska E, Faust MA, Tran KP, Chow F, Buglo E, Zhou F, Groziak MP, Xu HH. Identification of cellular targets of a series of boron heterocycles using TIPA II-A sensitive target identification platform. Bioorg Med Chem. 2016 Aug 1;24(15):3267-75. doi: 10.1016/j.bmc.2016.05.058. Epub 2016 Jun 4. PubMed PMID: 27301675; PubMed Central PMCID: PMC4992540. 7: Bommineni GR, Kapilashrami K, Cummings JE, Lu Y, Knudson SE, Gu C, Walker SG, Slayden RA, Tonge PJ. Thiolactomycin-Based Inhibitors of Bacterial β-Ketoacyl-ACP Synthases with in Vivo Activity. J Med Chem. 2016 Jun 9;59(11):5377-90. doi: 10.1021/acs.jmedchem.6b00236. Epub 2016 May 24. PubMed PMID: 27187871; PubMed Central PMCID: PMC4917603. 8: Chevalier F, Carrera LC, Nussaume L, Maréchal E. Chemical Genetics in Dissecting Membrane Glycerolipid Functions. Subcell Biochem. 2016;86:159-75. doi: 10.1007/978-3-319-25979-6_7. Review. PubMed PMID: 27023235. 9: Tao W, Yurkovich ME, Wen S, Lebe KE, Samborskyy M, Liu Y, Yang A, Liu Y, Ju Y, Deng Z, Tosin M, Sun Y, Leadlay PF. A genomics-led approach to deciphering the mechanism of thiotetronate antibiotic biosynthesis. Chem Sci. 2016 Jan 1;7(1):376-385. doi: 10.1039/c5sc03059e. Epub 2015 Oct 8. PubMed PMID: 28791099; PubMed Central PMCID: PMC5518548. 10: Tang X, Li J, Millán-Aguiñaga N, Zhang JJ, O'Neill EC, Ugalde JA, Jensen PR, Mantovani SM, Moore BS. Identification of Thiotetronic Acid Antibiotic Biosynthetic Pathways by Target-directed Genome Mining. ACS Chem Biol. 2015 Dec 18;10(12):2841-2849. doi: 10.1021/acschembio.5b00658. Epub 2015 Oct 21. PubMed PMID: 26458099; PubMed Central PMCID: PMC4758359. 11: Sabbagh G, Berakdar N. Docking studies of flavonoid compounds as inhibitors of β-ketoacyl acyl carrier protein synthase I (Kas I) of Escherichia coli. J Mol Graph Model. 2015 Sep;61:214-23. doi: 10.1016/j.jmgm.2015.07.005. Epub 2015 Jul 28. Erratum in: J Mol Graph Model. 2015 Nov;62():362. PubMed PMID: 26292066. 12: Parsons JB, Yao J, Frank MW, Rock CO. FabH mutations confer resistance to FabF-directed antibiotics in Staphylococcus aureus. Antimicrob Agents Chemother. 2015 Feb;59(2):849-58. doi: 10.1128/AAC.04179-14. Epub 2014 Nov 17. PubMed PMID: 25403676; PubMed Central PMCID: PMC4335864. 13: Schiebel J, Kapilashrami K, Fekete A, Bommineni GR, Schaefer CM, Mueller MJ, Tonge PJ, Kisker C. Structural basis for the recognition of mycolic acid precursors by KasA, a condensing enzyme and drug target from Mycobacterium tuberculosis. J Biol Chem. 2013 Nov 22;288(47):34190-204. doi: 10.1074/jbc.M113.511436. Epub 2013 Oct 9. PubMed PMID: 24108128; PubMed Central PMCID: PMC3837160. 14: Kapilashrami K, Bommineni GR, Machutta CA, Kim P, Lai CT, Simmerling C, Picart F, Tonge PJ. Thiolactomycin-based β-ketoacyl-AcpM synthase A (KasA) inhibitors: fragment-based inhibitor discovery using transient one-dimensional nuclear overhauser effect NMR spectroscopy. J Biol Chem. 2013 Mar 1;288(9):6045-52. doi: 10.1074/jbc.M112.414516. Epub 2013 Jan 10. PubMed PMID: 23306195; PubMed Central PMCID: PMC3585043. 15: Steinbrecher T, Case DA, Labahn A. Free energy calculations on the binding of novel thiolactomycin derivatives to E. coli fatty acid synthase I. Bioorg Med Chem. 2012 Jun 1;20(11):3446-53. doi: 10.1016/j.bmc.2012.04.019. Epub 2012 Apr 16. PubMed PMID: 22560835. 16: Schaefer B, Kisker C, Sotriffer CA. Molecular dynamics of Mycobacterium tuberculosis KasA: implications for inhibitor and substrate binding and consequences for drug design. J Comput Aided Mol Des. 2011 Nov;25(11):1053-69. doi: 10.1007/s10822-011-9483-4. Epub 2011 Nov 11. PubMed PMID: 22076471. 17: Roy KK, Bhunia SS, Saxena AK. CoMFA, CoMSIA, and docking studies on thiolactone-class of potent anti-malarials: identification of essential structural features modulating anti-malarial activity. Chem Biol Drug Des. 2011 Sep;78(3):483-93. doi: 10.1111/j.1747-0285.2011.01158.x. Epub 2011 Jul 13. PubMed PMID: 21672165. 18: Hans RH, Su H, Chibale K. Novel tetracyclic structures from the synthesis of thiolactone-isatin hybrids. Beilstein J Org Chem. 2010 Jul 19;6. pii: 78. doi: 10.3762/bjoc.6.78. PubMed PMID: 20703386; PubMed Central PMCID: PMC2919273. 19: Katane M, Saitoh Y, Hanai T, Sekine M, Furuchi T, Koyama N, Nakagome I, Tomoda H, Hirono S, Homma H. Thiolactomycin inhibits D-aspartate oxidase: a novel approach to probing the active site environment. Biochimie. 2010 Oct;92(10):1371-8. doi: 10.1016/j.biochi.2010.06.021. Epub 2010 Jul 29. PubMed PMID: 20603179. 20: Machutta CA, Bommineni GR, Luckner SR, Kapilashrami K, Ruzsicska B, Simmerling C, Kisker C, Tonge PJ. Slow onset inhibition of bacterial beta-ketoacyl-acyl carrier protein synthases by thiolactomycin. J Biol Chem. 2010 Feb 26;285(9):6161-9. doi: 10.1074/jbc.M109.077909. Epub 2009 Dec 16. PubMed PMID: 20018879; PubMed Central PMCID: PMC2825411.