Porothramycin A
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| Category | Antibiotics |
| Catalog number | BBF-02049 |
| CAS | 110652-73-8 |
| Molecular Weight | 343.38 |
| Molecular Formula | C18H21N3O4 |
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Description
Porothramycin A is an antibiotic produced by Str.albus K731-113. It has activity against gram-positive bacteria and anaerobic bacteria.
Specification
| Synonyms | Porothramycin; 2-Propenamide, N,N-dimethyl-3-(5,10,11,11a-tetrahydro-11-hydroxy-9-methoxy-5-oxo-1H-pyrrolo(2,1-c)(1,4)benzodiazepin-2-yl)-, (11R-(2(E),11-alpha,11a-beta))- |
| IUPAC Name | (E)-3-[(6R)-6-hydroxy-4-methoxy-11-oxo-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]-N,N-dimethylprop-2-enamide |
| Canonical SMILES | CN(C)C(=O)C=CC1=CN2C(C1)C(NC3=C(C2=O)C=CC=C3OC)O |
| InChI | InChI=1S/C18H21N3O4/c1-20(2)15(22)8-7-11-9-13-17(23)19-16-12(18(24)21(13)10-11)5-4-6-14(16)25-3/h4-8,10,13,17,19,23H,9H2,1-3H3/b8-7+/t13?,17-/m1/s1 |
| InChI Key | OQMYRVPMCIOFHL-GCOHUWJYSA-N |
Properties
| Appearance | Light Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 634.9°C at 760 mmHg |
| Melting Point | 140-150°C (dec.) |
| Density | 1.35 g/cm3 |
Reference Reading
1. Concise formal synthesis of porothramycins A and B via Zincke pyridinium ring-opening/ring-closing cascade
Theo D Michels, Matthew J Kier, Aaron M Kearney, Christopher D Vanderwal Org Lett. 2010 Jul 2;12(13):3093-5. doi: 10.1021/ol101035p.
Short formal syntheses of the antitumor antibiotics porothramycins A and B from a commercially available ester of the unnatural amino acid 3-(3-pyridyl)alanine are presented. A rearrangement cascade that presumably involves a Zincke-type pyridinium ring-opening followed by cyclization of a pendant nucleophilic amide generates the salient pyrroline ring of the alkaloids.
2. Reactivity and synthesis inspired by the Zincke ring-opening of pyridines
Christopher D Vanderwal J Org Chem. 2011 Dec 2;76(23):9555-67. doi: 10.1021/jo201625e. Epub 2011 Oct 20.
The century-old Zincke process for ring-opening of pyridinium salts produces 5-amino-2,4-pentadienals, a type of donor-acceptor dienes known as Zincke aldehydes. Inspired by this reasonably general and often efficient process for dearomatization, my laboratory has used pyridines as a starting point for heterocycle synthesis, which resulted in unusual syntheses of indoles, pyrrolines, and a formal synthesis of the natural product porothramycin A. Furthermore, our study of the reactivity of Zincke aldehydes has led to accidental discoveries of pericyclic cascade reactions that produce Z-α,β-unsaturated amides or polycyclic lactams, depending upon the identity of the substituents on nitrogen. Finally, a base-mediated formal cycloaddition reaction of tryptamine-derived Zincke aldehydes has served as the key step in concise syntheses of the indole alkaloids norfluorocurarine and strychnine.
3. Sequence analysis of porothramycin biosynthetic gene cluster
Lucie Najmanova, Dana Ulanova, Marketa Jelinkova, Zdenek Kamenik, Eliska Kettnerova, Marketa Koberska, Radek Gazak, Bojana Radojevic, Jiri Janata Folia Microbiol (Praha). 2014 Nov;59(6):543-52. doi: 10.1007/s12223-014-0339-x. Epub 2014 Aug 16.
The biosynthetic gene cluster of porothramycin, a sequence-selective DNA alkylating compound, was identified in the genome of producing strain Streptomyces albus subsp. albus (ATCC 39897) and sequentially characterized. A 39.7 kb long DNA region contains 27 putative genes, 18 of them revealing high similarity with homologous genes from biosynthetic gene cluster of closely related pyrrolobenzodiazepine (PBD) compound anthramycin. However, considering the structures of both compounds, the number of differences in the gene composition of compared biosynthetic gene clusters was unexpectedly high, indicating participation of alternative enzymes in biosynthesis of both porothramycin precursors, anthranilate, and branched L-proline derivative. Based on the sequence analysis of putative NRPS modules Por20 and Por21, we suppose that in porothramycin biosynthesis, the methylation of anthranilate unit occurs prior to the condensation reaction, while modifications of branched proline derivative, oxidation, and dimethylation of the side chain occur on already condensed PBD core. Corresponding two specific methyltransferase encoding genes por26 and por25 were identified in the porothramycin gene cluster. Surprisingly, also methyltransferase gene por18 homologous to orf19 from anthramycin biosynthesis was detected in porothramycin gene cluster even though the appropriate biosynthetic step is missing, as suggested by ultra high-performance liquid chromatography-diode array detection-mass spectrometry (UHPLC-DAD-MS) analysis of the product in the S. albus culture broth.
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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 ╳
