Suppr超能文献

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.
J Org Chem. 2011 Jun 17;76(12):5132-6. doi: 10.1021/jo200045a. Epub 2011 May 25.
6
Synthesis and asymmetric resolution of α-azido-peroxides.
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.
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.
ACS Chem Biol. 2012 Mar 16;7(3):581-9. doi: 10.1021/cb200510k. Epub 2012 Jan 24.

引用本文的文献

2
The McKenna reaction - avoiding side reactions in phosphonate deprotection.
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.
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.
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.
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.
Biochemistry. 2012 Oct 30;51(43):8491-501. doi: 10.1021/bi3010335. Epub 2012 Oct 19.
8
Stereospecific formation of a ternary complex of (S)-α,β-fluoromethylene-dATP with DNA pol β.
Chembiochem. 2012 Mar 5;13(4):528-30. doi: 10.1002/cbic.201100738. Epub 2012 Feb 7.

本文引用的文献

7
(R)-beta,gamma-fluoromethylene-dGTP-DNA ternary complex with DNA polymerase beta.
J Am Chem Soc. 2007 Dec 19;129(50):15412-3. doi: 10.1021/ja072127v. Epub 2007 Nov 22.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验