Pyrrolosporin A
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| Category | Antibiotics |
| Catalog number | BBF-02103 |
| CAS | |
| Molecular Weight | 841.81 |
| Molecular Formula | C44H54Cl2N2O10 |
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Description
Pyrrolosporin A is an antibiotic produced by Micromonospora sp. C39217-R1097. It has weak anti-Gram-negative bacteria activity.
Specification
| IUPAC Name | (1S,3S,6S,7E,10E,13R,16S,17S,18S,21R,22R)-17-[(2R,4R,5S,6R)-5-[(3,5-dichloro-1H-pyrrole-2-carbonyl)amino]-4-hydroxy-6-methyloxan-2-yl]oxy-3,22-diethyl-23-hydroxy-6,18-dimethyl-25,27-dioxo-26-oxapentacyclo[22.2.1.01,6.013,22.016,21]heptacosa-4,7,10,14,23-pentaene-4-carboxylic acid |
| Canonical SMILES | CCC1CC23C(=O)C(=C(C4(C5CCC(C(C5C=CC4CC=CCC=CC2(C=C1C(=O)O)C)OC6CC(C(C(O6)C)NC(=O)C7=C(C=C(N7)Cl)Cl)O)C)CC)O)C(=O)O3 |
| InChI | InChI=1S/C44H54Cl2N2O10/c1-6-24-20-44-38(51)33(41(55)58-44)37(50)43(7-2)25(12-10-8-9-11-17-42(44,5)21-27(24)40(53)54)14-15-26-28(43)16-13-22(3)36(26)57-32-19-30(49)34(23(4)56-32)48-39(52)35-29(45)18-31(46)47-35/h8,10-11,14-15,17-18,21-26,28,30,32,34,36,47,49-50H,6-7,9,12-13,16,19-20H2,1-5H3,(H,48,52)(H,53,54)/b10-8+,17-11+,37-33?/t22-,23+,24-,25+,26-,28+,30+,32-,34+,36-,42-,43+,44+/m0/s1 |
| InChI Key | LEJAZORDQAFJNR-FRZYJUKMSA-N |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 974.6±65.0°C at 760 mmHg |
| Melting Point | 235°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Antibacterial Spirotetronate Polyketides from an Actinomadura sp. Strain A30804
Kuan-Chieh Ching, Elaine J Chin, Mario Wibowo, Zann Y Tan, Lay-Kien Yang, Deborah C Seow, Chung-Yan Leong, Veronica W Ng, Siew-Bee Ng, Yoganathan Kanagasundaram Molecules. 2022 Nov 24;27(23):8196. doi: 10.3390/molecules27238196.
Large scale cultivation and chemical investigation of an extract obtained from Actimonadura sp. resulted in the identification of six previously undescribed spirotetronates (pyrrolosporin B and decatromicins C-G; 7-12), along with six known congeners, namely decatromicins A-B (1-2), BE-45722B-D (3-5), and pyrrolosporin A (6). The chemical structures of compounds 1-12 were characterized via comparison with previously reported data and analysis of 1D/2D NMR and MS data. The structures of all new compounds were highly related to the spirotetronate type compounds, decatromicin and pyrrolosporin, with variations in the substituents on the pyrrole and aglycone moieties. All compounds were evaluated for antibacterial activity against the Gram-negative bacteria, Acinetobacter baumannii and Gram-positive bacteria, Staphylococcus aureus and were investigated for their cytotoxicity against the human cancer cell line A549. Of these, decatromicin B (2), BE-45722B (3), and pyrrolosporin B (7) exhibited potent antibacterial activities against both Gram-positive (MIC90 between 1-3 μM) and Gram-negative bacteria (MIC90 values ranging from 12-36 μM) with weak or no cytotoxic activity against A549 cells.
2. Pyrrolosporin A, a new antitumor antibiotic from Micromonospora sp. C39217-R109-7. II. Isolation, physico-chemical properties, spectroscopic study and X-ray analysis
D R Schroeder, K L Colson, S E Klohr, M S Lee, J A Matson, L S Brinen, J Clardy J Antibiot (Tokyo). 1996 Sep;49(9):865-72. doi: 10.7164/antibiotics.49.865.
Pyrrolosporin A (1) is a new macrolide antitumor antibiotic possessing an unusual spiro-alpha-acyltetronic acid moiety. The antibiotic was isolated from the fermentation broth of Micromonospora sp. by vacuum liquid chromatography, crystallization and reversed phase HPLC (C18). The structure was determined by a combination of NMR, MS, IR, UV, X-ray analysis and degradation studies.
3. A cyclase that catalyses competing 2 + 2 and 4 + 2 cycloadditions
Hongbo Wang, Yike Zou, Miao Li, Zhijun Tang, Jiabao Wang, Zhenhua Tian, Nina Strassner, Qian Yang, Qingfei Zheng, Yujiao Guo, Wen Liu, Lifeng Pan, K N Houk Nat Chem. 2023 Feb;15(2):177-184. doi: 10.1038/s41557-022-01104-x. Epub 2023 Jan 23.
Cycloaddition reactions are among the most widely used reactions in chemical synthesis. Nature achieves these cyclization reactions with a variety of enzymes, including Diels-Alderases that catalyse concerted 4 + 2 cycloadditions, but biosynthetic enzymes with 2 + 2 cyclase activity have yet to be discovered. Here we report that PloI4, a β-barrel-fold protein homologous to the exo-selective 4 + 2 cyclase that functions in the biosynthesis of pyrroindomycins, catalyses competitive 2 + 2 and 4 + 2 cycloaddition reactions. PloI4 is believed to catalyse an endo-4 + 2 cycloaddition in the biosynthesis of pyrrolosporin A; however, when the substrate precursor of pyrroindomycins was treated with PloI4, an exo-2 + 2 adduct was produced in addition to the exo- and endo-4 + 2 adducts. Biochemical characterizations, computational analyses, (co)crystal structures and mutagenesis outcomes have allowed the catalytic versatility of PloI4 to be rationalized. Mechanistic studies involved the directed engineering of PloI4 to variants that produced the exo-4 + 2, endo-4 + 2 or exo-2 + 2 product preferentially. This work illustrates an enzymatic thermal 2 + 2 cycloaddition and provides evidence of a process through which an enzyme evolves along with its substrate for specialization and activity improvement.
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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 ╳
