Pseudouridimycin
(Synonyms: PUM) 目录号 : GC38466
Pseudouridimycin (PUM) 是一种抗生素，选择性细菌 RNA 聚合酶 (RNAP) 抑制剂。Pseudouridimycin 是一种 C-核苷类似物，对革兰氏阴性菌和革兰氏阳性菌均有效。
Cas No.:1566586-52-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Pseudouridimycin (PUM), an antibiotic, is a selective bacterial RNA polymerase (RNAP) inhibitor. Pseudouridimycin is a C-nucleoside analogue that is effective against both Gram-negative and Gram-positive bacteria[1].
[1]. Rosenqvist P, et al. Characterization of C-nucleoside Antimicrobials from Streptomyces albus DSM 40763: Strepturidin is Pseudouridimycin. Sci Rep. 2019 Jun 20;9(1):8935.
| Cas No. | 1566586-52-4 | SDF | |
| 别名 | PUM | ||
| Canonical SMILES | N=C(N)NCC(N([C@H](C(NC[C@H]1O[C@@H](C(C(N2)=O)=CNC2=O)[C@H](O)[C@@H]1O)=O)CCC(O)=O)O)=O | ||
| 分子式 | C17H25N7O10 | 分子量 | 487.42 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.0516 mL | 10.2581 mL | 20.5162 mL |
| 5 mM | 0.4103 mL | 2.0516 mL | 4.1032 mL |
| 10 mM | 0.2052 mL | 1.0258 mL | 2.0516 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Total Synthesis of Pseudouridimycin
Org Lett 2022 Jan 21;24(2):511-515.PMID:35005956DOI:10.1021/acs.orglett.1c03914.
Pseudouridimycin (1), a potent antibiotic against both Gram-positive and Gram-negative bacteria including multi-drug-resistant strains with a new mode of action isolated from Streptomyces sp., was synthesized by a convergent strategy from 5'-amino-pseudouridine 5 and N-hydroxy-dipeptide 26 in 23% total yield. The key intermediate 26 was synthesized by hydroxylaminolysis of the nitrone derived from glutamine and subsequent glycylation with glycine chloride. The synthetic method provides an efficient and practical way for the synthesis of N-hydroxylated peptidyl nucleoside.
Total synthesis and chemical stability of Pseudouridimycin
Chem Commun (Camb) 2022 Feb 15;58(14):2351-2354.PMID:35080211DOI:10.1039/d1cc07059b.
We report the chemical synthesis of Pseudouridimycin (1), an antimicrobial natural product that potently and selectively inhibits bacterial RNA polymerase. Chemical stability studies revealed intramolecular hydroxamate bond scission to be a major decomposition pathway for 1 in aqueous buffer. Replacement of the hydroxamate bond with a tertiary amide, as in 16, afforded a conformational isostere resistant to degradation. These studies pave the way for the design and synthesis of analogues with improved chemical stability and biological activity.
Correction: Total synthesis and chemical stability of Pseudouridimycin
Chem Commun (Camb) 2022 Feb 22;58(16):2762.PMID:35141739DOI:10.1039/d2cc90056d.
Correction for 'Total synthesis and chemical stability of Pseudouridimycin' by Christopher F. Cain et al., Chem. Commun., 2022, DOI: 10.1039/d1cc07059b.
Total synthesis of Pseudouridimycin and its epimer via Ugi-type multicomponent reaction
Chem Commun (Camb) 2022 Jul 14;58(57):7956-7959.PMID:35757838DOI:10.1039/d2cc02442j.
A total synthesis of Pseudouridimycin (1) was accomplished featuring an unusual oxime Ugi-type multicomponent condensation to simultaneously construct the dipeptide moiety of this peptidyl nucleoside antibiotic. In this synthetic route 1 is readily accessible via a longest linear sequence of 9 synthetic steps from pseudouridine. This strategy can be applicable to a variety of Pseudouridimycin analogues.
Discovery, properties, and biosynthesis of Pseudouridimycin, an antibacterial nucleoside-analog inhibitor of bacterial RNA polymerase
J Ind Microbiol Biotechnol 2019 Mar;46(3-4):335-343.PMID:30465105DOI:10.1007/s10295-018-2109-2.
Pseudouridimycin (PUM) is a novel pseudouridine-containing peptidyl-nucleoside antibiotic that inhibits bacterial RNA polymerase (RNAP) through a binding site and mechanism different from those of clinically approved RNAP inhibitors of the rifamycin and lipiarmycin (fidaxomicin) classes. PUM was discovered by screening microbial fermentation extracts for RNAP inhibitors. In this review, we describe the discovery and characterization of PUM. We also describe the RNAP-inhibitory and antibacterial properties of PUM. Finally, we review available information on the gene cluster and pathway for PUM biosynthesis and on the potential for discovering additional novel pseudouridine-containing nucleoside antibiotics by searching bacterial genome and metagenome sequences for sequences similar to pumJ, the pseudouridine-synthase gene of the PUM biosynthesis gene cluster.