6-Chloropurine Riboside
(Synonyms: 6-氯嘌呤核苷) 目录号 : GC49551
A nucleoside precursor
Cas No.:5399-87-1
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
6-Chloropurine riboside is a nucleoside precursor.1 It has been used in the synthesis of adenosine derivatives with antiproliferative activity in human gastric cancer cells expressing the adenosine A3 receptor. 6-Chloropurine riboside has also been used in the synthesis of N6-benzyladenosine derivatives with antiproliferative activity in a variety of cancer cells or inhibitory activity against T. gondii replication in CRL-1634/Hs27 human skin fibroblasts.2,3
1.Zurita, F.V., Vega, N.B., and Cabrera, M.G.Semisynthesis, characterization and evaluation of new adenosine derivatives as antiproliferative agentsMolecules23(5)1111(2018) 2.Dolezal, K., Popa, I., HauserovÁ, E., et al.Preparation, biological activity and endogenous occurrence of N6-benzyladenosinesBioorg. Med. Chem.15(11)3737-3747(2007) 3.Kim, Y.A., Sharon, A., Chu, C.K., et al.Synthesis, biological evaluation and molecular modeling studies of N6-benzyladenosine analogues as potential anti-toxoplasma agentsBiochem. Pharmacol.73(10)1558-1572(2007)
| Cas No. | 5399-87-1 | SDF | Download SDF |
| 别名 | 6-氯嘌呤核苷 | ||
| Canonical SMILES | ClC1=C(N=CN2[C@]3([H])O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1 | ||
| 分子式 | C10H11ClN4O4 | 分子量 | 286.7 |
| 溶解度 | DMF: 2 mg/ml,DMSO: 5 mg/ml,Ethanol: insol,PBS (pH 7.2): insol | 储存条件 | -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 | 3.488 mL | 17.4398 mL | 34.8797 mL |
| 5 mM | 0.6976 mL | 3.488 mL | 6.9759 mL |
| 10 mM | 0.3488 mL | 1.744 mL | 3.488 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。
Modification of bovine pancreatic ribonuclease A with 6-Chloropurine Riboside
Arch Biochem Biophys 1986 May 1;246(2):681-9.PMID:3707127DOI:10.1016/0003-9861(86)90324-3.
The chemical modification of bovine pancreatic ribonuclease A by 6-Chloropurine Riboside was studied to obtain information about the role of the purine nucleoside moiety of the ribonucleic acid in the enzyme-substrate interaction. The residues involved in the reaction were identified, after performic acid oxidation and trypsin digestion, by reverse-phase HPLC peptide mapping. The labeled peptides were detected by following the absorbance at 254 nm, and amino acid analyses of these peptides showed that the reaction had taken place with the amino groups of Lys-1, -37, -41, and -91. The specificity of the reaction was unaffected by changing the ligand:protein molar ratio. Partial separation of the reaction products was accomplished by means of chromatography on CM-Sepharose: four labeled fractions corresponding to mono- and bisubstituted derivatives were found. One of the monosubstituted fractions (fraction E) contained a homogeneous protein with the nucleoside bound to the alpha-amino group of Lys-1 whereas the other (fraction D) was a mixture of derivatives labeled in the epsilon-amino group of Lys-1, -37, -41, and -91. Kinetic studies of these two monosubstituted fractions were performed with cytidine 2',3'-phosphate and ribonucleic acid as substrates. These derivatives showed a noncompetitive inhibition-like behavior with respect to RNase A. Results support the existence of several RNase A regions with affinity for purine nucleosides.
General Approach to N6,C5'-Difunctionalization of Adenosine
J Org Chem 2022 Jan 7;87(1):18-39.PMID:34905365DOI:10.1021/acs.joc.1c01587.
Among the C6-halo purine ribonucleosides, the readily accessible 6-chloro derivative has been known to undergo slow SNAr reactions with amines, particularly aryl amines. In this work, we show that in 0.1 M AcOH in EtOH, aryl amines react quite efficiently at the C6-position of 2',3',5'-tri-O-(t-BuMe2Si)-protected 6-Chloropurine Riboside (6-ClP-riboside), with concomitant cleavage of the 5'-silyl group. These two-step processes proceeded in generally good yields, and notably, reactions in the absence of AcOH were much slower and/or lower yielding. Corresponding reactions of 2',3',5'-tri-O-(t-BuMe2Si)-protected 6-ClP-riboside with alkyl amines proceeded well but without desilylation at the primary hydroxyl terminus. These differences are likely due to the acidities of the ammonium chlorides formed in these reactions, and the role of AcOH was not desilylation but possibly only purine activation. With 50% aqueous TFA in THF at 0 °C, cleavage of the 5'-silyl group from 2',3',5'-tri-O-(t-BuMe2Si)-protected N6-alkyl adenosine derivatives and from 6-ClP-riboside was readily achieved. Reactions of the 5'-deprotected 6-ClP-riboside with alkyl amines proceeded in high yields and under mild conditions. Because these complementary methodologies yielded N6-aryl and -alkyl adenosine derivatives containing a free 5'-hydroxyl group, a variety of product functionalizations were undertaken to yield N6,C5'-doubly modified nucleoside analogues.
Introduction of a benzoyl group onto 6-Chloropurine Riboside in aqueous solution and its application to the synthesis of nucleoside derivatives
Nucleic Acids Symp Ser 2000;(44):103-4.PMID:12903289DOI:10.1093/nass/44.1.103.
A benzoyl group was introduced onto the 3'-hydroxyl group of 6-Chloropurine Riboside by treatment with benzoic anhydride in the presence of a base in aqueous solution. The product (3b) was converted to 9-(2,3-Di-deoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (1, FddA) in 6 steps, including radical deoxygenation.
Reaction of bovine pancreatic ribonuclease A with 6-Chloropurine Riboside 5'-monophosphate. Nuclear magnetic resonance studies of the corresponding S-peptide
Int J Pept Protein Res 1980 Oct;16(4):241-4.PMID:6257620doi
The n.m.r. spectra of native S-peptide and of S-peptide II, a derivative obtained after reaction of bovine pancreatic ribonuclease A with 6-Chloropurine Riboside 5'-monophosphate, both in D2O and in urea-d4, were obtained with a 270 MHz Fourier transform spectrometer. From these spectra it was possible to assign most of the proton resonances of the peptide and the position of the labelling group, the alpha-NH2 of Lys-1, was also deduced.
Synthesis of fluorinated nucleosides
Curr Protoc Nucleic Acid Chem 2006 Jul;Chapter 1:Unit 1.12.PMID:18428944DOI:10.1002/0471142700.nc0112s25.
Two practical synthetic approaches to the production of lodenosine [FddA, 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine] via 6-Chloropurine Riboside or 6-chloropurine 3'-deoxyriboside are described. The reaction sequence contains new fluorination methods and new applications of radical reduction. The reagents and reaction conditions of each step have been carefully selected to ensure robustness and safety.