α-叠氮双膦酸盐：合成与核苷酸类似物。
α-Azido bisphosphonates: synthesis and nucleotide analogues.
机构信息
Department of Chemistry, University of Southern California, Los Angeles, California 90089-0744, USA.
出版信息
J Org Chem. 2011 Jun 17;76(12):5132-6. doi: 10.1021/jo200045a. Epub 2011 May 25.
Abstract
The first examples of α-azido bisphosphonates (RO)(2)P(O)CXN(3) (1, R = i-Pr, X = Me; 2, R = i-Pr, X = H; 3, R = H, X = Me; 4, R = H, X = H) and corresponding β,γ-CXN(3) dGTP (5-6) and α,β-CXN(3) dATP (7-8) analogues are described. The individual diastereomers of 7 (7a/b) were obtained by HPLC separation of the dADP synthetic precursor (14a/b).
摘要
描述了首例 α-叠氮双膦酸盐 (RO)(2)P(O)CXN(3) (1, R = i-Pr, X = Me; 2, R = i-Pr, X = H; 3, R = H, X = Me; 4, R = H, X = H) 和相应的β,γ-CXN(3) dGTP (5-6) 和 α,β-CXN(3) dATP (7-8) 类似物。通过 HPLC 分离 dADP 合成前体 (14a/b)，得到了 7 (7a/b) 的各个非对映异构体。
相似文献
1
α-Azido bisphosphonates: synthesis and nucleotide analogues.α-叠氮双膦酸盐：合成与核苷酸类似物。
J Org Chem. 2011 Jun 17;76(12):5132-6. doi: 10.1021/jo200045a. Epub 2011 May 25.
2
β,γ-CHF- and β,γ-CHCl-dGTP diastereomers: synthesis, discrete 31P NMR signatures, and absolute configurations of new stereochemical probes for DNA polymerases.β,γ-CHF- 和 β,γ-CHCl-dGTP 非对映异构体：新型 DNA 聚合酶立体化学探针的合成、离散 31P NMR 特征和绝对构型。
J Am Chem Soc. 2012 May 30;134(21):8734-7. doi: 10.1021/ja300218x. Epub 2012 May 18.
3
Synthesis of 3-azido-2,3,6-trideoxy-beta-D-arabino-hexopyranosyl pyranonaphthoquinone analogues of medermycin.美登霉素的3-叠氮基-2,3,6-三脱氧-β-D-阿拉伯己吡喃糖基吡喃萘醌类似物的合成
Org Biomol Chem. 2003 May 21;1(10):1690-700. doi: 10.1039/b301449p.
4
Trimethylsilylnitrate-trimethylsilyl azide: a novel reagent system for the synthesis of 2-deoxyglycosyl azides from glycals. Application in the synthesis of 2-deoxy-beta-N-glycopeptides.硝酸三甲基硅酯-叠氮化三甲基硅：一种用于从糖烯合成2-脱氧糖基叠氮化物的新型试剂体系。在2-脱氧-β-N-糖肽合成中的应用。
J Org Chem. 2004 Apr 2;69(7):2630-3. doi: 10.1021/jo0354948.
5
Diverse modes of reactivity of dialkyl azodicarboxylates with P(III) compounds: synthesis, structure, and reactivity of products other than the Morrison-Brunn-Huisgen intermediate in a Mitsunobu-type reaction.偶氮二甲酸二烷基酯与P(III)化合物的多种反应模式：在光延反应类型中除莫里森-布伦-惠斯根中间体之外的产物的合成、结构及反应活性
J Org Chem. 2004 Mar 19;69(6):1880-9. doi: 10.1021/jo035634d.
6
Synthesis and asymmetric resolution of α-azido-peroxides.α-叠氮过氧化物的合成与对映体拆分。
Org Lett. 2013 Aug 2;15(15):3832-5. doi: 10.1021/ol401443a. Epub 2013 Jul 15.
7
Strain-promoted double-click reaction for chemical modification of azido-biomolecules.应变促进的叠氮生物分子化学修饰的双击反应。
Org Biomol Chem. 2010 Sep 21;8(18):4051-5. doi: 10.1039/c0ob00003e. Epub 2010 Jul 26.
8
2'-Azido RNA, a versatile tool for chemical biology: synthesis, X-ray structure, siRNA applications, click labeling.2'-叠氮基 RNA，一种用于化学生物学的多功能工具：合成、X 射线结构、siRNA 应用、点击标记。
ACS Chem Biol. 2012 Mar 16;7(3):581-9. doi: 10.1021/cb200510k. Epub 2012 Jan 24.
9
Highly stereoselective synthesis of aristeromycin through dihydroxylation of 4-aryl-1-azido-2-cyclopentenes.通过4-芳基-1-叠氮基-2-环戊烯的二羟基化反应高立体选择性合成阿瑞霉素。
J Org Chem. 2004 Feb 6;69(3):655-9. doi: 10.1021/jo034672u.
10
Completing the β,γ-CXY-dNTP Stereochemical Probe Toolkit: Synthetic Access to the dCTP Diastereomers and P and F NMR Correlations with Absolute Configurations.完成β,γ-CXY-dNTP 立体化学探针工具包：dCTP 非对映异构体的合成途径以及与绝对构型的 P 和 F NMR 相关性。
J Org Chem. 2020 Nov 20;85(22):14592-14609. doi: 10.1021/acs.joc.0c01204. Epub 2020 Oct 30.
引用本文的文献
1
Bisphosphonates: The role of chemistry in understanding their biological actions and structure-activity relationships, and new directions for their therapeutic use.双膦酸盐：化学在理解其生物学作用和构效关系以及治疗用途的新方向中的作用。
Bone. 2022 Mar;156:116289. doi: 10.1016/j.bone.2021.116289. Epub 2021 Dec 8.
2
The McKenna reaction - avoiding side reactions in phosphonate deprotection.麦肯纳反应——避免膦酸酯脱保护中的副反应
Beilstein J Org Chem. 2020 Jun 23;16:1436-1446. doi: 10.3762/bjoc.16.119. eCollection 2020.
3
Remarkably Stereospecific Utilization of ATP α,β-Halomethylene Analogues by Protein Kinases.令人瞩目的蛋白激酶对 ATP α,β-卤代亚甲基类似物的立体特异性利用。
J Am Chem Soc. 2017 Jun 14;139(23):7701-7704. doi: 10.1021/jacs.7b03266. Epub 2017 Jun 2.
4
Transition state in DNA polymerase β catalysis: rate-limiting chemistry altered by base-pair configuration.DNA 聚合酶 β催化中的过渡态：碱基对构象改变的限速化学反应。
Biochemistry. 2014 Mar 25;53(11):1842-8. doi: 10.1021/bi500101z. Epub 2014 Mar 12.
5
Nucleoside triphosphates--building blocks for the modification of nucleic acids.核苷三磷酸——修饰核酸的结构单元。
Molecules. 2012 Nov 15;17(11):13569-91. doi: 10.3390/molecules171113569.
6
Effect of β,γ-CHF- and β,γ-CHCl-dGTP halogen atom stereochemistry on the transition state of DNA polymerase β.β,γ-CHF-和β,γ-CHCl-dGTP 卤原子立体化学对 DNA 聚合酶 β 过渡态的影响。
Biochemistry. 2012 Oct 30;51(43):8491-501. doi: 10.1021/bi3010335. Epub 2012 Oct 19.
7
β,γ-CHF- and β,γ-CHCl-dGTP diastereomers: synthesis, discrete 31P NMR signatures, and absolute configurations of new stereochemical probes for DNA polymerases.β,γ-CHF- 和 β,γ-CHCl-dGTP 非对映异构体：新型 DNA 聚合酶立体化学探针的合成、离散 31P NMR 特征和绝对构型。
J Am Chem Soc. 2012 May 30;134(21):8734-7. doi: 10.1021/ja300218x. Epub 2012 May 18.
8
Stereospecific formation of a ternary complex of (S)-α,β-fluoromethylene-dATP with DNA pol β.（S）-α，β-氟亚甲基-dATP 与 DNA 聚合酶β形成三元复合物的立体专一性。
Chembiochem. 2012 Mar 5;13(4):528-30. doi: 10.1002/cbic.201100738. Epub 2012 Feb 7.
本文引用的文献
1
Reactions of Benzocyclic β-Keto Esters with Sulfonyl Azides. 2. Further Insight into the Influence of Azide Structure and Solvent on the Reaction Course.苯并环β-酮酯与磺酰叠氮化物的反应。2. 对叠氮化物结构和溶剂对反应过程影响的进一步深入了解。
J Org Chem. 1999 Jul 9;64(14):5132-5138. doi: 10.1021/jo9901541.
2
Halogenated beta,gamma-methylene- and ethylidene-dGTP-DNA ternary complexes with DNA polymerase beta: structural evidence for stereospecific binding of the fluoromethylene analogues.含卤素的β,γ-亚甲基-和亚乙基-dGTP-DNA 三元复合物与 DNA 聚合酶β：氟亚甲基类似物的立体特异性结合的结构证据。
J Am Chem Soc. 2010 Jun 9;132(22):7617-25. doi: 10.1021/ja909370k.
3
Generation of iminyl copper species from alpha-azido carbonyl compounds and their catalytic C-C bond cleavage under an oxygen atmosphere.从α-叠氮羰基化合物中生成亚氨基铜物种及其在氧气氛围下的催化 C-C 键断裂。
Org Lett. 2010 May 7;12(9):2052-5. doi: 10.1021/ol100522z.
4
A direct preparation of N-unsubstituted pyrrole-2,5-dicarboxylates from 2-azidocarboxylic esters.由2-叠氮基羧酸酯直接制备N-未取代的吡咯-2,5-二羧酸酯。
Org Lett. 2009 Oct 1;11(19):4282-5. doi: 10.1021/ol901637w.
5
Alpha,beta-difluoromethylene deoxynucleoside 5'-triphosphates: a convenient synthesis of useful probes for DNA polymerase beta structure and function.α,β-二氟亚甲基脱氧核苷5'-三磷酸：一种用于DNA聚合酶β结构与功能研究的有用探针的简便合成方法
Org Lett. 2009 May 7;11(9):1883-6. doi: 10.1021/ol701755k.
6
DNA polymerase beta fidelity: halomethylene-modified leaving groups in pre-steady-state kinetic analysis reveal differences at the chemical transition state.DNA聚合酶β的保真度：稳态前动力学分析中卤代亚甲基修饰的离去基团揭示了化学过渡态的差异。
Biochemistry. 2008 Jan 22;47(3):870-9. doi: 10.1021/bi7014162. Epub 2007 Dec 28.
7
(R)-beta,gamma-fluoromethylene-dGTP-DNA ternary complex with DNA polymerase beta.(R)-β,γ-氟亚甲基-dGTP与DNA聚合酶β形成的DNA三元复合物
J Am Chem Soc. 2007 Dec 19;129(50):15412-3. doi: 10.1021/ja072127v. Epub 2007 Nov 22.
8
ELEMENTAL SELENIUM GENERATED BY THE PHOTOBLEACHING OF SELENOMEROCYANINE PHOTOSENSITIZERS FORMS CONJUGATES WITH SERUM MACROMOLECULES THAT ARE TOXIC TO TUMOR CELLS.由硒代亚甲蓝光敏剂光漂白产生的元素硒与对肿瘤细胞有毒性的血清大分子形成缀合物。
Phosphorus Sulfur Silicon Relat Elem. 2005;180(3-4):647-657. doi: 10.1080/10426500590907200.
Zotero 插件