Puromycin

Base Information

• Chemical Name: Puromycin
• CAS No.: 53-79-2
• Molecular Formula: C22H29 N7 O5
• Molecular Weight: 471.516
• European Community (EC) Number: 200-387-8
• UNII: 4A6ZS6Q2CL
• DSSTox Substance ID: DTXSID8036788
• Nikkaji Number: J2.310H
• Wikipedia: Puromycin
• Wikidata: Q424696,Q27167243
• NCI Thesaurus Code: C787
• Metabolomics Workbench ID: 51097
• ChEMBL ID: CHEMBL469912
• Mol file: 53-79-2.mol

Synonyms:CL 13900;CL-13900;CL13900;P 638;P-638;P638;Puromycin;Puromycin Dihydrochloride;Puromycin Hydrochloride;Stylomycin

Chemical Property of Puromycin

Chemical Property:

• Vapor Pressure: 8.44E-30mmHg at 25°C
• Melting Point: 175.5-177°
• Refractive Index: 1.7010 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 6.8, 7.2(at 25℃)
• Flash Point: °C
• PSA: 160.88000
• Density: 1.51 g/cm³
• LogP: 0.29750
• Water Solubility.: Soluble in water (50 mg/ml at 20°C).
• XLogP3: 0
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 471.22301705
• Heavy Atom Count: 34
• Complexity: 680

Purity/Quality:

99%, ^*data from raw suppliers

Puromycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic to living cells of all kinds.
• Hazard Codes: Toxic to living cells of all kinds.

MSDS Files:

SDS file from LookChem

Useful:

• 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
• Description: Puromycin is an aminonucleoside antibiotic produced by Streptomyces alboniger. It is a very common antibiotic routinely used by scientists in biomedical research to select cells modified by genetic engineering. It specifically inhibits peptidyl transfer on both prokaryotic and eukaryotic ribosomes. The antibiotic inhibits the growth of Gram-positive bacteria and various animal and insect cells. Fungi and Gram-negative bacteria are resistant due to the low permeability of the antibiotic. For more than 30 years, puromycin has been widely used as a basic tool for studying protein synthesis. Now, puromycin hydrochloride is particularly useful for the selection of cell types harboring plasmids carrying puromycin resistance genes. Puromycinresistant cells express pac gene, which encodes an N-acetyl puromycin transferase. The pac gene can be mobilized on a plasmid and used to transfect a host cell in an attempt to provide resistance; therefore, puromycin can be used in gene selections for mammalian host cells. This aminonucleoside antibiotic causes premature chain termination during translation in the ribosomes. Part of the molecule resembles the 30 end of the aminoacylated tRNA. It enters the A site and transfers to the growing chain, causing premature chain release. The exact mechanism of action is unknown, but the 30 position contains an amide linkage instead of the normal ester linkage of tRNA; the amide bond makes the molecule much more resistant to hydrolysis and thus causes the ribosome to become stopped. It is not selective for either prokaryotes or eukaryotes. Also of note, puromycin is critical in mRNA display as it allows the growing peptide chain to be covalently bonded to its own mRNA template. Additionally, puromycin is a reversible inhibitor of dipeptidyl-peptidase II (serine peptidase) and cytosol alanyl aminopeptidase (metallopeptidase). The mechanism of inhibition is not well understood; however, puromycin can be used to distinguish between aminopeptidase M (active) and cytosol alanyl aminopeptidase (inhibited by puromycin) and therefore extremely useful in biochemistry and nephrology research.
• Uses: Puromycin has been widely used as a basic tool in research for studying protein synthesis. It is an antibiotic used by scientists in bioresearch to select cells modified by genetic engineering. It inhibits protein synthesis by binding to RNA. It is also an antineoplastic and antitrypanosomal agent. Puromycin is a nucleoside antibiotic isolated from Streptomyces alboniger in the 1950s as an anti-trypansomal agent with antibiotic activity. Puromycin is non-selective, inhibiting RNA by blocking ribosomal translation. Puromycin is used in cell biology to select mammalian cell lines that have been transformed by vectors that express puromycin-N-acetyl-transferase. Puromycin is an aminonuclease antibiotic produced by the soil actinomycete?Streptomyces alboniger; which induces apoptosis.

Technology Process of Puromycin

There total 28 articles about Puromycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 45.0%

6-dimethylamino-9-[3'-(O-methyl) (2S)-N-benzyloxycarbonyltyrosinylamino-3'-deoxy-β-D-ribofuranosyl]purine (57182-86-2) → puromycin (53-79-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 5h;

DOI:10.1002/(SICI)1099-1344(200005)43:6<623::AID-JLCR347>3.0.CO;2-O

Reference yield: 36.0%

tert-butyl [(S)-1-({(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl}amino)-3-(4-methoxyphenyl)-1-oxopropan-2yl]carbamate (57183-05-8) → puromycin (53-79-2)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 0.133333h;

DOI:10.1021/jo010935d

Reference yield:

9-[3-(benzylamino)-3-deoxy-β-D-ribofuranosyl]adenine (67313-10-4,134934-82-0) → puromycin (53-79-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / NH₄HCO₂ / Pd(OH)2-C / H₂O; methanol / 1.5 h / Heating

2: pyridine / 48 h / 5 °C

3: 59.4 mg / TMSCl / pyridine

4: 25.8 mg / pyridine; H₂O / 19 h / 20 °C

5: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C

6: 36 percent / TFA / 0.13 h / 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; chloro-trimethyl-silane; ammonium formate; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium hydroxide - carbon; In pyridine; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo010935d

upstream raw materials:

6-dimethylamino-9-[3'-(O-methyl) (2S)-N-benzyloxycarbonyltyrosinylamino-3'-deoxy-β-D-ribofuranosyl]purine

tert-butyl [(S)-1-({(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl}amino)-3-(4-methoxyphenyl)-1-oxopropan-2yl]carbamate

3'-Trifluoracetamido-3'-desoxyadenosin

9-[3-(benzylamino)-3-deoxy-β-D-ribofuranosyl]adenine

Refernces

• 1、 Chung, Clive Yik Sham,Timblin, Greg A.,Saijo, Kaoru,Chang, Christopher J.. "Versatile Histochemical Approach to Detection of Hydrogen Peroxide in Cells and Tissues Based on Puromycin Staining". . p. 6109 - 6121. Retrieved 2018/05/26.
• 2、 -. "ESTERASES FOR MONITORING PROTEIN BIOSYNTHESIS IN VITRO". . . Retrieved 2009/10/21.