Capuramycin
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| Category | Antibiotics |
| Catalog number | BBF-00216 |
| CAS | 102770-00-3 |
| Molecular Weight | 569.52 |
| Molecular Formula | C23H31N5O12 |
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Description
Capuramycin is a nucleoside antibiotic produced by Streptomyces griseus 446-S3. It has activity against Streptococcus pneumoniae and Mycobacterium smegmatis, but has no effect on other bacteria and fungi.
Specification
| Synonyms | Antibiotic 446S3-1 |
| IUPAC Name | (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-N-[(3S)-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide |
| Canonical SMILES | COC1C(C(OC1C(C(=O)N)OC2C(C(C=C(O2)C(=O)NC3CCCCNC3=O)O)O)N4C=CC(=O)NC4=O)O |
| InChI | InChI=1S/C23H31N5O12/c1-37-15-14(32)21(28-7-5-12(30)27-23(28)36)39-16(15)17(18(24)33)40-22-13(31)10(29)8-11(38-22)20(35)26-9-4-2-3-6-25-19(9)34/h5,7-10,13-17,21-22,29,31-32H,2-4,6H2,1H3,(H2,24,33)(H,25,34)(H,26,35)(H,27,30,36)/t9-,10-,13-,14+,15-,16-,17+,21+,22+/m0/s1 |
| InChI Key | BISOEENGZHMDEO-RLXIHFJVSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 173-176°C |
| Density | 1.6 g/cm3 |
Reference Reading
1. An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin
Haiqing He, Lili Xu, Roujing Sun, Yunqin Zhang, Yingying Huang, Zixi Chen, Penghua Li, Rui Yang, Guozhi Xiao Chem Sci. 2021 Feb 23;12(14):5143-5151. doi: 10.1039/d0sc06815b.
Both glycans (O-glycosides) and nucleosides (N-glycosides) play important roles in numerous biological processes. Chemical synthesis is a reliable and effective means to solve the attainability issues of these essential biomolecules. However, due to the stereo- and regiochemical issues during glycan assembly, together with problems including the poor solubility and nucleophilicity of nucleobases in nucleoside synthesis, the development of one-pot glycosylation strategies toward efficient synthesis of both glycans and nucleosides remains poor and challenging. Here, we report the first orthogonal and reactivity-based one-pot glycosylation strategy suitable for both glycan and nucleoside synthesis on the basis of glycosyl ortho-(1-phenylvinyl)benzoates. This one-pot glycosylation strategy not only inherits the advantages including no aglycon transfers, no undesired interference of departing species, and no unpleasant odors associated with the previously developed orthogonal one-pot glycosylation strategy based on glycosyl ortho-alkynylbenzoates, but also highly expands the scope (glycans and nucleosides) and increases the number of leaving groups that could be employed for the multistep one-pot synthesis (up to the formation of four different glycosidic bonds). In particular, the current one-pot glycosylation strategy is successfully applied to the total synthesis of a promising tuberculosis drug lead capuramycin and the divergent and formal synthesis of TMG-chitotriomycin with potent and specific inhibition activities toward β-N-acetylglucosaminidases and important endosymbiotic lipochitooligosaccharides including the Nod factor and the Myc factor, which represents one of the most efficient and straightforward synthetic routes toward these biologically salient molecules.
2. Synthesis of capuramycin and its analogues via a Ferrier-type I reaction and their biological evaluation
Shintaro Kusaka, Kazuki Yamamoto, Motoko Shinohara, Yusuke Minato, Satoshi Ichikawa Bioorg Med Chem. 2022 Nov 1;73:117011. doi: 10.1016/j.bmc.2022.117011. Epub 2022 Sep 26.
The total synthesis of capuramycin (1), which is a promising anti-tubercular antibiotics, has been accomplished using Ferrier-type I reaction as a key step. This total synthesis is an alternative approach to the synthesis of capuramycin and its analogues. The 3'-O-demethyl analogue (2), which exhibits an equivalent antibacterial activity as capuramycin (1) against Mycobacterium smegmatis and Mycobacterium avium, is suggested to have potential as a lead structure of capuramycin analogues because 2 is more accessible from a synthetic view point.
3. DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors
Katsuhiko Mitachi, Rita G Kansal, Kirk E Hevener, Cody D Gillman, Syed M Hussain, Hyun Gi Yun, Gustavo A Miranda-Carboni, Evan S Glazer, William M Clemons Jr, Michio Kurosu J Med Chem. 2020 Oct 8;63(19):10855-10878. doi: 10.1021/acs.jmedchem.0c00545. Epub 2020 Sep 18.
Capuramycin displays a narrow spectrum of antibacterial activity by targeting bacterial translocase I (MraY). In our program of development of new N-acetylglucosaminephosphotransferase1 (DPAGT1) inhibitors, we have identified that a capuramycin phenoxypiperidinylbenzylamide analogue (CPPB) inhibits DPAGT1 enzyme with an IC50 value of 200 nM. Despite a strong DPAGT1 inhibitory activity, CPPB does not show cytotoxicity against normal cells and a series of cancer cell lines. However, CPPB inhibits migrations of several solid cancers including pancreatic cancers that require high DPAGT1 expression in order for tumor progression. DPAGT1 inhibition by CPPB leads to a reduced expression level of Snail but does not reduce E-cadherin expression level at the IC50 (DPAGT1) concentration. CPPB displays a strong synergistic effect with paclitaxel against growth-inhibitory action of a patient-derived pancreatic adenocarcinoma, PD002: paclitaxel (IC50: 1.25 μM) inhibits growth of PD002 at 0.0024-0.16 μM in combination with 0.10-2.0 μM CPPB (IC50: 35 μM).
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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 ╳
