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Merck
CN

PZ0182

Pactamycin

≥95% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C28H38N4O8
CAS Number:
23668-11-3
Molecular Weight:
558.62
UNSPSC Code:
51101500
PubChem Substance ID:
329823756
MDL number:
MFCD00158126

Key Documents

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InChI

1S/C28H38N4O8/c1-15-9-7-12-20(35)21(15)24(36)40-14-27(39)23(30-19-11-8-10-18(13-19)16(2)33)22(29)28(17(3)34,26(27,4)38)31-25(37)32(5)6/h7-13,17,22-23,30,34-35,38-39H,14,29H2,1-6H3,(H,31,37)/t17-,22-,23-,26-,27+,28-/m0/s1

SMILES string

C[C@H](O)[C@]1(NC(=O)N(C)C)[C@@H](N)[C@H](Nc2cccc(c2)C(C)=O)[C@](O)(COC(=O)c3c(C)cccc3O)[C@]1(C)O

InChI key

WVIUOSJLUCTGFK-JUJPXXQGSA-N

assay

≥95% (HPLC)

form

powder

optical activity

[α]/D +20 to +30° in 95% ethanol

color

white to tan

solubility

DMSO: ≥12 mg/mL

storage temp.

2-8°C

Biochem/physiol Actions

Antitumor antibiotic
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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
081M4701V

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A S Mankin
Journal of molecular biology, 274(1), 8-15 (1998-01-10)
Mutants of an archaeon Halobacterium halobium, resistant to the universal inhibitor of translation, pactamycin, were isolated. Pactamycin resistance correlated with the presence of mutations in the 16 S rRNA gene of H. halobium single rRNA operon. Three types of mutations
Total synthesis of pactamycin.
Stephen Hanessian et al.
Angewandte Chemie (International ed. in English), 50(15), 3497-3500 (2011-03-04)
Hwei L Ong et al.
Pflugers Archiv : European journal of physiology, 453(6), 797-808 (2006-12-16)
Store-operated Ca(2+) entry (SOCE) is activated in response to depletion of intracellular Ca(2+) from the endoplasmic reticulum (ER). A variety of agonists stimulate SOCE via IP(3)-dependent Ca(2+) depletion. SOCE is also activated by thapsigargin, an inhibitor of Ca(2+) reuptake into
George Dinos et al.
Molecular cell, 13(1), 113-124 (2004-01-21)
The crystal structures of the universal translation-initiation inhibitors edeine and pactamycin bound to ribosomal 30S subunit have revealed that edeine induces base pairing of G693:C795, residues that constitute the pactamycin binding site. Here, we show that base pair formation by
Spencer Knapp et al.
Organic letters, 9(7), 1359-1362 (2007-03-07)
[structure: see text]. Pactamycin, one of the most complex and densely functionalized aminocyclitol antibiotics known, presents synthetic challenges that include reactivity and sterics, relative and absolute stereochemistry, and functional group compatibility and protection. An approach is reported that features four
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