D-Ribonolactone
(Synonyms: D-核糖内酯) 目录号 : GC60793
D-Ribonolactone是一种糖内酯，也是一种大肠杆菌β-半乳糖苷酶(β-galactosidase)的抑制剂，Ki为26mM。
Cas No.:5336-08-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
D-Ribonolactone is sugar lactone and an inhibitor of β-galactosidase of Escherichia coli with a Ki of 26 mM[1].
Ki: 26 mM (β-galactosidase)
[1]. Huber RE, et al. Strong inhibitory effect of furanoses and sugar lactones on beta-galactosidase Escherichia coli. Biochemistry. 1987 Mar 24;26(6):1526-31.
| Cas No. | 5336-08-3 | SDF | |
| 别名 | D-核糖内酯 | ||
| Canonical SMILES | O=C1[C@H](O)[C@H](O)[C@@H](CO)O1 | ||
| 分子式 | C5H8O5 | 分子量 | 148.11 |
| 溶解度 | DMSO : 125 mg/mL (843.97 mM; Need ultrasonic) | 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.7517 mL | 33.7587 mL | 67.5174 mL |
| 5 mM | 1.3503 mL | 6.7517 mL | 13.5035 mL |
| 10 mM | 0.6752 mL | 3.3759 mL | 6.7517 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。
Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides
Beilstein J Org Chem 2018 Apr 5;14:772-785.PMID:29719574DOI:10.3762/bjoc.14.65.
C-nucleosides have intrigued biologists and medicinal chemists since their discovery in 1950's. In that regard, C-nucleosides and their synthetic analogues have resulted in promising leads in drug design. Concurrently, advances in chemical syntheses have contributed to structural diversity and drug discovery efforts. Convergent and modular approaches to synthesis have garnered much attention in this regard. Among them nucleophilic substitution at C1' has seen wide applications providing flexibility in synthesis, good yields, the ability to maneuver stereochemistry as well as to incorporate structural modifications. In this review, we describe recent reports on the modular synthesis of C-nucleosides with a focus on D-Ribonolactone and sugar modifications that have resulted in potent lead molecules.
Carbocyclic analogues of D-ribose-5-phosphate: synthesis and behavior with 5-phosphoribosyl alpha-1-pyrophosphate synthetases
Bioorg Med Chem 1996 Jul;4(7):1077-88.PMID:8831979DOI:10.1016/0968-0896(96)00090-9.
The synthesis of cyclopentyl and cyclopentenyl analogues of the alpha-anomer of D-ribose-5-phosphate from D-Ribonolactone and D-ribose is described. These analogues, which have the same absolute configuration as D-ribose-5-phosphate, were incubated with PRPP synthetases in an attempt to prepare the corresponding carbocyclic PRPP analogues. The carbocyclic ribose-5-phosphate analogues were found to be inhibitors, rather than substrates, for 5-phosphoribosyl alpha-1-pyrophosphate synthetases of both bacterial and human origin. The inhibitory behaviour of the analogues is described.
A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones: intermediates in the synthesis of 2(3H)-furanones
Carbohydr Res 1994 Feb 3;253:207-23.PMID:8156548DOI:10.1016/0008-6215(94)80066-9.
A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-Ribonolactone. By a route that proceeded via 5-O-protected D-Ribonolactone, 5-O-protected 2,3-dideoxy-D-glycero-pent-2-enono-1,4-lactones were synthesized and reacted with R2CuLi or a complex PhSCu(RMgBr)n to give respectively the 3-C-alkyl or 3-C-phenyl compounds. Details of the preparation of the O-protected intermediates, as well as the selection of the organometallic reagents, are provided.
Stereoselective synthesis of 4'-selenonucleosides using the Pummerer glycosylation reaction
Carbohydr Res 2008 Jul 21;343(10-11):1790-800.PMID:18316068DOI:10.1016/j.carres.2008.02.014.
The syntheses of four selenonucleosides, namely 4'-beta-selenoadenosine, -cytidine, -thymidine, and -uridine are described. Commercially available D-Ribonolactone was converted to the key intermediate 1,4-anhydro-4-seleno-D-ribitol in seven steps in overall excellent yield. Oxidation of the seleno-d-ribitol with MCPBA gave a single diastereomeric selenoxide in excellent yield, which upon Pummerer reaction in the presence of silylated purine or pyrimidine bases gave stereoselectively the corresponding 4'-beta-selenonucleosides. The stereochemistry at the anomeric center was determined by means of 1D-NOE experiments.
Toward a general strategy for the synthesis of 3,4-dihydroxyprolines from pentose sugars
J Org Chem 2002 Jun 28;67(13):4466-74.PMID:12076143DOI:10.1021/jo025538x.
A general strategy is proposed, wherein a pentose sugar gamma-lactone can be converted, via a series of nine reactions, to a 3,4-dihydroxyproline, suitably protected for use in peptide synthesis. Thus, D-Ribonolactone (6) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-D-2,3-cis-3,4-cis-proline (7) in 18.9% overall yield. Likewise, L-arabinonolactone (11) has been converted to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-cis-3,4-trans-proline (36) in 13.7% overall yield and L-lyxonolactone (12) to N-fluorenylmethoxycarbonyl-3,4-di-O-tert-butyldimethylsilyloxy-L-2,3-trans-3,4-cis-proline (37) in 11.2% overall yield. These building blocks have also been fully deprotected to give the free amino acids. We believe that this series of reactions ought to be applicable to the synthesis of any of the eight stereoisomers of 3,4-dihydroxyproline, by judicious selection of the pentose starting material.