A problem solving approach for the diastereoselective synthesis of (5′S)- and (5′R)-5′,8-cyclopurine lesions

被引：9

作者：

Chatgilialoglu, Chryssostomos ^{[1
,2
]}

Ferreri, Carla ^{[1
]}

Masi, Annalisa ^{[1
]}

Sansone, Anna ^{[1
]}

Terzidis, Michael A. ^{[1
]}

Tsakos, Michail ^{[1
,3
]}

机构：

[1] CNR, Ist Sintesi Organ & Fotoreattivita, I-40129 Bologna, Italy

[2] NCSR Demokritos, Inst Nanosci & Nanotechnol, GR-15310 Athens, Greece

[3] Univ Athens, Dept Chem, Lab Organ Chem, Athens 15771, Greece

来源：

Organic Chemistry Frontiers | 2014年 / 1卷 / 06期

关键词：

DNA LESIONS; RADICAL CYCLIZATION; (5'R)-5'; 8-CYCLO-2'-DEOXYGUANOSINE; (5'S)-5'; GENERATION;

D O I：

10.1039/c4qo00133h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short, efficient and high-yielding approach for the diastereoselective syntheses of the four (5'S)- and (5'R)-5',8-cyclopurine lesions and their phosphoramidites has been developed. The intermediates prepared by these synthetic pathways provide an easy access to those modified nucleosides that constitute an important molecular library for recognition of DNA damage. With respect to previous synthesis, the key methodologies for cyclization steps and phosphoramidite synthesis were ameliorated.

引用

页码：698 / 702

页数：5

共 50 条

[21] Stereoselective Approach towards the Synthesis of 3R, 5 S Gingerdiol and 3 S, 5 S Gingerdiol
Markad, Sachin B.
Bhosale, Viraj A.
Bokale, Suvarna R.
Waghmode, Suresh B.
CHEMISTRYSELECT, 2019, 4 (02): : 502 - 505
[22] A SYNTHETIC APPROACH TO FAURINONE (9(R)-ACETYL-8(S)-METHYL-5(R)-ISOPROPYL HYDRINDANE) - SYNTHESIS OF 9(S)-ACETYL-8(R)-METHYL-5(R)-ISOPROPYL HYDRINDANE
BURNELL, RH
LEROUX, M
SYNTHETIC COMMUNICATIONS, 1983, 13 (07) : 559 - 567
[23] Diastereoselective synthesis of optically active (2R,5R)-hexanediol
J. Haberland
A. Kriegesmann
E. Wolfram
W. Hummel
A. Liese
Applied Microbiology and Biotechnology, 2002, 58 : 595 - 599
[24] Diastereoselective synthesis of optically active (2R,5R)-hexanediol
Haberland, J
Kriegesmann, A
Wolfram, E
Hummel, W
Liese, A
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2002, 58 (05) : 595 - 599
[25] 8,5′-Cyclopurine lesions as biomarkers for monitoring the oxidative stress arising from exposure to 6-thioguanine
Fu, Lijuan
Zhang, Fan
Wang, Yinsheng
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[26] An Assumption-Based Approach for Solving the Minimal S5-Satisfiability Problem
Lagniez, Jean-Marie
Le Berre, Daniel
de Lima, Tiago
Montmirail, Valentin
AUTOMATED REASONING, IJCAR 2018, 2018, 10900 : 1 - 18
[27] SYNTHESIS OF CARBON-BRIDGED 8,5'-CYCLOPURINE NUCLEOSIDES - NUCLEOSIDES AND NUCLEOTIDES .24.
MATSUDA, A
TEZUKA, M
NIIZUMA, K
SUGIYAMA, E
UEDA, T
TETRAHEDRON, 1978, 34 (17) : 2633 - 2637
[28] Total Synthesis of (3S, 5R, 3′S, 5′R)-Capsorubin
Frederico, Daniel
Constantino, Mauricio G.
Donate, Paulo M.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2009, 20 (05) : 888 - U148
[29] The case for 8,5′-cyclopurine-2′-deoxynucleosides as endogenous DNA lesions that cause neurodegeneration in xeroderma pigmentosum
Brooks, P. J.
NEUROSCIENCE, 2007, 145 (04) : 1407 - 1417
[30] Replication studies of oxidatively induced 8′5-cyclopurine-2′-deoxynucleosides
Swanson, Ashley L.
Wang, Jianshuang
Wang, Yinsheng
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244

← 1 2 3 4 5 →