puromycin

Also known as 3'-(L-alpha-Amino-p-methoxyhydrocinnamamido)-3'-deoxy-N,N-dimethyladenosine, (S)-3'-((2-Amino-3-(4-methoxyphenyl)-1-oxopropyl)amino)-3'-deoxy-N,N-dimethyladenosine, 9-{3-deoxy-3-[(O-methyl-L-tyrosyl)amino]-beta-D-xylofuranosyl}-N,N-dimethyl-9H-purin-6-amine, Achromycin

Puromycin is an antibiotic protein synthesis inhibitor which causes premature chain termination during translation.

Chemical data

Formula: C22H29N7O5
Molecular weight: 471.5 g/mol
IUPAC name: (2S)-2-amino-N-[(2S,3S,4R,5R)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(4-methoxyphenyl)propanamide
SMILES: CN(C)C1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)NC(=O)[C@H](CC4=CC=C(C=C4)OC)N)O
InChIKey: RXWNCPJZOCPEPQ-NVWDDTSBSA-N
XLogP: 0
Polar surface area: 161 Å²
H-bond donors: 4
H-bond acceptors: 10
Formal charge: 0

via PubChem

Research

9,314 papers

PUROMYCIN INHIBITION OF PROTEIN SYNTHESIS.Pharmacological reviews · 1964
Selecting Transgenic Mosquito Larvae with Puromycin.Cold Spring Harbor protocols · 2024
Cell type-specific labeling of newly synthesized proteins by puromycin inactivation.The Journal of biological chemistry · 2023
Puromycin: action on neuronal mitochondria.Science (New York, N.Y.) · 1968
Application of puromycin aminonucleoside and adriamycin to induce chronic renal failure in the rat.Contributions to nephrology · 1988

via PubMed

Wikidata facts

Mass: 471.223

Show 5 more facts

chemical formula: C₂₂H₂₉N₇O₅
Commons category: Puromycin
canonical SMILES: CN(C)C1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)NC(=O)C(CC4=CC=C(C=C4)OC)N)O
isomeric SMILES: CN(C)C1=NC=NC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)NC(=O)[C@H](CC4=CC=C(C=C4)OC)N)O
World Health Organisation international non-proprietary name: puromycin

Sources (3)

via Wikidata · CC0

~4 min read

Article

7 sections

Contents

Inhibition of translation
Peptidase inhibitor
Cell culture
Selection of ''Escherichia coli''
Selection of yeast
Memory loss in mice
References

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Puromycin is an antibiotic protein synthesis inhibitor which causes premature chain termination during translation.