Pactamycin
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| Category | Antibiotics |
| Catalog number | BBF-02665 |
| CAS | 23668-11-3 |
| Molecular Weight | 558.62 |
| Molecular Formula | C28H38N4O8 |
| Purity | ≥95% |
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Description
It is produced by the strain of Str. pactum var. pactum NRRL 2939. It is a cyclopentane and cyclohexane derivative antibiotic. It has anti-bacterial, virus, tumor activity.
Specification
| Synonyms | NSC-52947; Benzoic acid, 2-hydroxy-6-methyl-, [(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; (5-((3-Acetylphenyl)amino)-4-amino-3-(((dimethylamino)carbonyl)amino)-1,2-dihydroxy-3-(1-hydroxyethyl)-2-methylcyclopentyl)methyl 2-hydroxy-6-methylbenzoate, (1S-(1alpha,2beta,3alpha,3(R*),4alpha,5beta))- |
| Storage | Store at 2-8°C |
| IUPAC Name | [(1S,2R,3R,4S,5S)-5-(3-acetylanilino)-4-amino-3-(dimethylcarbamoylamino)-1,2-dihydroxy-3-[(1S)-1-hydroxyethyl]-2-methylcyclopentyl]methyl 2-hydroxy-6-methylbenzoate |
| Canonical SMILES | CC1=C(C(=CC=C1)O)C(=O)OCC2(C(C(C(C2(C)O)(C(C)O)NC(=O)N(C)C)N)NC3=CC=CC(=C3)C(=O)C)O |
| InChI | 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 |
| InChI Key | WVIUOSJLUCTGFK-JUJPXXQGSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Viruses; Bacteria |
| Boiling Point | 784.2°C at 760 mmHg |
| Density | 1.38 g/cm3 |
| Solubility | Soluble in Ethanol, DMSO |
Reference Reading
1. Synthetic Studies on Pactamycin: A Synthesis of Johnson's Intermediate
Junichiro Kanazawa, Toshiyuki Kan, Mitsuru Kondo, Masanobu Uchiyama, Makoto Inai, Hitoshi Ouchi, Yusuke Miura, Fumihiko Yoshimura, Taisei Osawa Org Lett . 2020 May 1;22(9):3515-3518. doi: 10.1021/acs.orglett.0c00959.
A formal total synthesis of pactamycin (1) has been accomplished by face-selective and regioselective nitroso Diels-Alder (NDA) reaction of acyl nitroso compound14, which contains a camphorsultam chiral auxiliary, and chiral cyclopentadiene12. Construction of the chiral secondary alcohol of12was performed by (S,S)-Ts-DENEB catalyst-mediated reduction, and the NDA adduct15awas readily converted to Johnson's intermediate21.
2. Asymmetric Synthesis and Biological Activities of Pactamycin-Inspired Aminocyclopentitols
Arup K Indra, Corey J Brumsted, Taifo Mahmud, Evan L Carpenter Org Lett . 2018 Jan 19;20(2):397-400. doi: 10.1021/acs.orglett.7b03681.
Pactamycin is a structurally unique aminocyclitol antibiotic with broad-spectrum cell growth inhibitory activity. To explore the bountiful activity of the aminocyclitol core of pactamycin, an efficient, modular, and asymmetric synthesis of aminocyclopentitols resembling the pactamycin pharmacophore has been developed employing a SmI2-mediated imino-pinacol coupling strategy. Two of the compounds exhibited antitumor activity against A375 melanoma cells.
3. The secondary metabolite pactamycin with potential for pharmaceutical applications: biosynthesis and regulation
Auday A Eida, Taifo Mahmud Appl Microbiol Biotechnol . 2019 Jun;103(11):4337-4345. doi: 10.1007/s00253-019-09831-x.
The antitumor antibiotic pactamycin is a highly substituted aminocyclopentitol-derived secondary metabolite produced by the soil bacterium Streptomyces pactum. It has exhibited potent antibacterial, antitumor, antiviral, and antiprotozoal activities. Despite its outstanding biological activities, the complex chemical structure and broad-spectrum toxicity have hampered its development as a therapeutic, limiting its contribution to biomedical science to a role as a molecular probe for ribosomal function. However, a detailed understanding of its biosynthesis and how the biosynthesis is regulated has made it possible to tactically design and produce new pactamycin analogues, some of which have shown improved pharmacological properties. This mini-review describes the biosynthesis, regulation, engineered production, and biological activities of pactamycin and its congeners. It also highlights the suitability of biosynthetic methods as a feasible approach to generate new analogues of complex natural products and underscores the importance of utilizing biosynthetic enzymes as tools for chemoenzymatic production of structurally diverse bioactive compounds.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
