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PZ0182 Sigma

Pactamycin

≥95% (HPLC)

Synonym: 2-Hydroxy-6-methylbenzoic acid [(1S,2R,3R,4S,5S)-5-[(3-acetylphenyl)amino]-4-amino-3-[[(dimethylamino)carbonyl]amino]-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentyl]methyl ester, PNU-0015800, U-15800

  • CAS Number 23668-11-3

  • Empirical Formula (Hill Notation) C28H38N4O8

  • Molecular Weight 558.62

  •  MDL number MFCD00158126

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
assay   ≥95% (HPLC)
form   powder
optical activity   [α]/D +20 to +30° in 95% ethanol
color   white to tan
solubility   DMSO: ≥12 mg/mL
originator   Pfizer
storage temp.   2-8°C

Description

Legal Information

Sold for research purposes under agreement from Pfizer Inc.

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Biochem/physiol Actions

Pactamycin is a potent protein synthesis inhibitor, inhibiting protein synthesis at the translocation step on the 70S ribosome. It has activity against Gram-positive and Gram-negative bacteria, and broad antitumor, antiviral, and antiplasmodial activity. Cytotoxicity limits it clinical use.

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This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T+
Risk Statements (Europe) 
Safety Statements (Europe) 
26-28-36/37-45
RIDADR 
UN 2811 6.1 / PGII
WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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Diastereocontrolled construction of pactamycin's complex ureido triol functional array. Malinowski JT, McCarver SJ, and Johnson JS Org. Lett. 14(11), 2878-81, (2012)

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Total synthesis of pactamycin. Hanessian S, Vakiti RR, Dorich S, et al. Angew. Chem. Int. Ed. Engl. 50(15), 3497-500, (2011)

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Total synthesis of pactamycin and pactamycate: a detailed account. Hanessian S, Vakiti RR, Dorich S, et al. J. Org. Chem. 77(21), 9458-72, (2012)

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Crystal structure of a bioactive pactamycin analog bound to the 30S ribosomal subunit. Tourigny DS, Fernández IS, Kelley AC, et al. J. Mol. Biol. 425(20), 3907-10, (2013)

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Probing functional diversity in pactamycin toward antibiotic, antitumor, and antiprotozoal activity. Hanessian S, Vakiti RR, Chattopadhyay AK, et al. Bioorg. Med. Chem. 21(7), 1775-86, (2013)

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Synthesis of the oxygenated pactamycin core. Knapp S and Yu Y Org. Lett. 9(7), 1359-62, (2007)

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Rapid induction of apoptosis mediated by peptides that bind initiation factor eIF4E. Herbert TP, Fåhraeus R, Prescott A, et al. Curr. Biol. 10(13), 793-6, (2000)

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Chemistry. Pactamycin made easy. Codelli JA and Reisman SE Science 340(6129), 152-3, (2013)

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Cloning of the pactamycin biosynthetic gene cluster and characterization of a crucial glycosyltransferase prior to a unique cyclopentane ring formation. Kudo F, Kasama Y, Hirayama T, Eguchi T. J. Antibiot. 60, 492-503, (2007)

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The structural basis for the action of the antibiotics tetracycline, pactamycin, and hygromycin B on the 30S ribosomal subunit. Brodersen DE, Clemons WM Jr, Carter AP, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V Cell 103, 1143-1154, (2000)

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Estradiol regulates estrogen receptor mRNA stability. Saceda M, Lindsey RK, Solomon H, et al. J. Steroid Biochem. Mol. Biol. 66(3), 113-20, (1998)

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Enantioselective synthesis of pactamycin, a complex antitumor antibiotic. Malinowski JT, Sharpe RJ, and Johnson JS Science 340(6129), 180-2, (2013)

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Dissecting the ribosomal inhibition mechanisms of edeine and pactamycin: the universally conserved residues G693 and C795 regulate P-site RNA binding. Dinos G, Wilson DN, Teraoka Y, et al. Mol. Cell. 13(1), 113-24, (2004)

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Biosynthetic Studies and Genetic Engineering of Pactamycin Analogs with Improved Selectivity toward Malarial Parasites. Lu W, Roongsawang N, Mahmud T. Chem. Biol. 18, 425-431, (2011)

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Deciphering pactamycin biosynthesis and engineered production of new pactamycin analogues. Ito T, Roongsawang N, Shirasaka N, et al. ChemBioChem. 10(13), 2253-65, (2009)

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The host gene for intronic U17 small nucleolar RNAs in mammals has no protein-coding potential and is a member of the 5'-terminal oligopyrimidine gene family. Pelczar P and Filipowicz W Mol. Cell. Biol. 18(8), 4509-18, (1998)

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AUG sequences are required to sustain nonsense-codon-mediated suppression of splicing. Kamhi E, Yahalom G, Kass G, et al. Nucleic Acids Res. 34(12), 3421-33, (2006)

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Intracellular Ca(2+) release via the ER translocon activates store-operated calcium entry. Ong HL, Liu X, Sharma A, et al. Pflugers Arch. 453(6), 797-808, (2007)

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The phosphorylation of protein S6 modulates the interaction of the 40 S ribosomal subunit with the 5'-untranslated region of a dictyostelium pre-spore-specific mRNA and controls its stability. Chiaberge S, Cassarino E, and Mangiarotti G J. Biol. Chem. 273(42), 27070-5, (1998)

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Pactamycin resistance mutations in functional sites of 16 S rRNA. Mankin AS J. Mol. Biol. 274(1), 8-15, (1997)

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Ribosomal release without peptidyl tRNA hydrolysis at translation termination in a eukaryotic system. Cao J and Geballe AP RNA 4(2), 181-8, (1998)

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Promising lead compounds for novel antiprotozoals. Otoguro K, Iwatsuki M, Ishiyama A, et al. J. Antibiot. 63(7), 381-4, (2010)

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Diastereoselective synthesis of vicinal tertiary diols. Loertscher BM, Young PR, Evans PR, et al. Org. Lett. 15(8), 1930-3, (2013)

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Analysis of rRNA processing and translation in mammalian cells using a synthetic 18S rRNA expression system. Burman LG and Mauro VP Nucleic Acids Res. 40(16), 8085-98, (2012)

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Stimulation of Sendai virus C' protein synthesis by cycloheximide. Gupta KC and Ono E Biochem. J. 321 ( Pt 3), 811-8, (1997)

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Translational control of terminal oligopyrimidine mRNAs requires a specific regulator. Loreni F and Amaldi F FEBS Lett. 416(3), 239-42, (1997)

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