Pyralomicin 1a
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| Category | Antibiotics |
| Catalog number | BBF-02086 |
| CAS | 139636-03-6 |
| Molecular Weight | 456.27 |
| Molecular Formula | C20H19Cl2NO7 |
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Description
Pyralomicin 1a is an antibiotic produced by Actinomadura spiralis MI 178-34F18. Antibacterial activity.
Specification
| IUPAC Name | 2,6-dichloro-1-[(1R,4R,5R,6S)-5,6-dihydroxy-3-(hydroxymethyl)-4-methoxycyclohex-2-en-1-yl]-5-hydroxy-8-methylchromeno[2,3-b]pyrrol-4-one |
| Canonical SMILES | CC1=CC(=C(C2=C1OC3=C(C2=O)C=C(N3C4C=C(C(C(C4O)O)OC)CO)Cl)O)Cl |
| InChI | InChI=1S/C20H19Cl2NO7/c1-7-3-10(21)15(26)13-14(25)9-5-12(22)23(20(9)30-18(7)13)11-4-8(6-24)19(29-2)17(28)16(11)27/h3-5,11,16-17,19,24,26-28H,6H2,1-2H3/t11-,16+,17-,19-/m1/s1 |
| InChI Key | JPPZZIRKTBZEAJ-JLBIYAHBSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | bacteria |
| Boiling Point | 604.9±55.0°C at 760 mmHg |
| Melting Point | 297-300°C (dec.) |
| Density | 1.7±0.1 g/cm3 |
Reference Reading
1. Biosynthesis of the cyclitol moiety of pyralomicin 1a in Nonomuraea spiralis MI178-34F18
Hiroshi Naganawa, Hideki Hashizume, Yumiko Kubota, Ryuichi Sawa, Yoshikazu Takahashi, Kenji Arakawa, Simeon G Bowers, Taifo Mahmud J Antibiot (Tokyo). 2002 Jun;55(6):578-84. doi: 10.7164/antibiotics.55.578.
The biosynthetic pathway leading to the cyclitol moiety of pyralomicin 1a (1) in Nonomuraea spiralis MI178-34F18 has been studied using a series of 2H-labeled potential precursors. The results demonstrate that 2-epi-5-epi-valiolone (7), a common precursor for acarbose (4) and validamycin A (5) biosynthesis, is an immediate precursor of pyralomicin 1a. 5-epi-Valiolone (8) was also incorporated into 1, albeit less efficiently than 7. Other potential intermediates, such as valiolone (9), valienone (10), valienol (11), 1-epi-valienol (12), 5-epi-valiolol (13), and 1-epi-5-epi-valiolol (14) were not incorporated into pyralomicin 1a. To explain this surprising observation, it is proposed that either 2-epi-5-epi-valiolone (7) is specifically activated (e.g., to its phosphate) and that the further transformations take place on activated intermediates (which can not be generated directly from their unactivated counterparts), or that the transformation of 7 into 1 involves a substrate-channeling mechanism in which enzyme-bound intermediates are directly transferred from one enzyme active site to the next in a multi-enzyme complex.
2. Genetic insights into pyralomicin biosynthesis in Nonomuraea spiralis IMC A-0156
Patricia M Flatt, Xiumei Wu, Steven Perry, Taifo Mahmud J Nat Prod. 2013 May 24;76(5):939-46. doi: 10.1021/np400159a. Epub 2013 Apr 22.
The biosynthetic gene cluster for the pyralomicin antibiotics has been cloned and sequenced from Nonomuraea spiralis IMC A-0156. The 41 kb gene cluster contains 27 ORFs predicted to encode all of the functions for pyralomicin biosynthesis. This includes nonribosomal peptide synthetases (NRPS) and polyketide synthases (PKS) required for the formation of the benzopyranopyrrole core unit, as well as a suite of tailoring enzymes (e.g., four halogenases, an O-methyltransferase, and an N-glycosyltransferase) necessary for further modifications of the core structure. The N-glycosyltransferase is predicted to transfer either glucose or a pseudosugar (cyclitol) to the aglycone. A gene cassette encoding C7-cyclitol biosynthetic enzymes was identified upstream of the benzopyranopyrrole-specific ORFs. Targeted disruption of the gene encoding the N-glycosyltransferase, prlH, abolished pyralomicin production, and recombinant expression of PrlA confirms the activity of this enzyme as a sugar phosphate cyclase involved in the formation of the C7-cyclitol moiety.
3. The C7N aminocyclitol family of natural products
Taifo Mahmud Nat Prod Rep. 2003 Feb;20(1):137-66. doi: 10.1039/b205561a.
This review covers microbial secondary metabolites classified in the family of C7N aminocyclitols, a relatively new class of natural products that is increasingly gaining recognition due to their significant biomedical and agricultural uses. Their discovery and structure determinations, their biosynthetic origin, biological properties, chemical synthesis, as well as their further development for pharmaceutical uses are described. The literature from 1970 to July 2002 is reviewed, with 269 references cited.
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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 ╳
