Carbocyclic puromycin

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

MedKoo CAT#: 412312

CAS#: 104264-92-8

Description: Carbocyclic puromycin is a biochemical

Chemical Structure

Carbocyclic puromycin
CAS# 104264-92-8

Theoretical Analysis

MedKoo Cat#: 412312
Name: Carbocyclic puromycin
CAS#: 104264-92-8
Chemical Formula: C23H31N7O4
Exact Mass: 469.2438
Molecular Weight: 469.55
Elemental Analysis: C, 58.83; H, 6.65; N, 20.88; O, 13.63

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Carbocyclic puromycin; Puromycin, carbocyclic

IUPAC/Chemical Name: Benzenepropanamide, alpha-amino-N-(3-(6-(dimethylamino)-9H-purin-9-yl)-2-hydroxy-5-(hydroxymethyl)cyclopentyl)-4-methoxy-, (1S-(1alpha(R*),2alpha,3beta,5beta))-


InChi Code: InChI=1S/C23H31N7O4/c1-29(2)21-19-22(26-11-25-21)30(12-27-19)17-9-14(10-31)18(20(17)32)28-23(33)16(24)8-13-4-6-15(34-3)7-5-13/h4-7,11-12,14,16-18,20,31-32H,8-10,24H2,1-3H3,(H,28,33)/t14-,16-,17-,18-,20+/m0/s1

SMILES Code: O=C(N[C@@H]1[C@H](O)[C@@H](N2C=NC3=C(N(C)C)N=CN=C23)C[C@H]1CO)[C@@H](N)CC4=CC=C(OC)C=C4

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: >3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 469.55 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

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1: Vince R, Daluge S, Brownell J. Carbocyclic puromycin: synthesis and inhibition of protein biosynthesis. J Med Chem. 1986 Nov;29(11):2400-3. doi: 10.1021/jm00161a044. PMID: 3783599.

2: Cesario C, Tardibono LP Jr, Miller MJ. Syntheses of carbocyclic aminonucleosides and (-)-epi-4'-carbocyclic puromycin: Application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations. Tetrahedron Lett. 2010 Jun 9;51(23):3053-3056. doi: 10.1016/j.tetlet.2010.04.006. PMID: 20640052; PMCID: PMC2903068.

3: Vince R, Daluge S. Puromycin analogs. Studies on ribosomal binding with diastereomeric carbocyclic puromycin analogs. J Med Chem. 1974 Jun;17(6):578-83. doi: 10.1021/jm00252a003. PMID: 4598021.

4: Vince R, Daluge S, Palm M. Inhibition of in vitro protein synthesis by a carbocyclic puromycin analog. Biochem Biophys Res Commun. 1972 Jan 31;46(2):866-70. doi: 10.1016/s0006-291x(72)80221-3. PMID: 4550700.

5: Vince R, Daluge S. Synthesis of cyclohexyl carbocyclic puromycin and its inhibition of protein synthesis. J Med Chem. 1977 Jul;20(7):930-4. doi: 10.1021/jm00217a013. PMID: 327067.

6: Daluge S, Vince R. Synthesis and antimicrobial activity of a carbocyclic puromycin analog. 6-Dimethylamino-9-(R(2R-hydroxy-3R-(p-methoxyphenyl-L alanylamino))-cyclopentyl)purine. J Med Chem. 1972 Feb;15(2):171-7. doi: 10.1021/jm00272a012. PMID: 4621466.