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

[31] ISOLATION AND CHARACTERIZATION OF (5R,6S,5'R,8'R)-LUTEOCHROME AND (5R,6S,5'R,8'S)-LUTEOCHROME FROM BRAZILIAN SWEET-POTATOES (IPOMOEA-BATATAS LAM)
DEALMEIDA, LB
PENTEADO, MDC
SIMPSON, KL
BRITTON, G
ACEMOGLU, M
EUGSTER, CH
HELVETICA CHIMICA ACTA, 1986, 69 (07) : 1554 - 1558
[32] Stereoselective synthesis of (2R,5R)- and (2S,5R)-5-hydroxylysine
van den Nieuwendijk, AMCH
Kriek, NMAJ
Brussee, J
van Boom, JH
van der Gen, A
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (22) : 3683 - 3691
[33] Synthesis of [5′-2H1]-nucleosides with defined (5′S)/(5′R)-ratios
Oogo, Y
Ono, A
Ono, A
Kainosho, M
TETRAHEDRON LETTERS, 1998, 39 (18) : 2873 - 2876
[34] STEREOSPECIFIC SYNTHESIS OF 5S-HETE, 5R-HETE AND THEIR TRANSFORMATION TO 5(+/-)HPETE
ZAMBONI, R
ROKACH, J
TETRAHEDRON LETTERS, 1983, 24 (10) : 999 - 1002
[35] Diastereoselective synthesis of 5-benzylthio- and 5-mercaptohexahydropyrimidin-2-ones
Fesenko, Anastasia A.
Shutalev, Anatoly D.
TETRAHEDRON LETTERS, 2007, 48 (48) : 8420 - 8423
[36] Asymmetric synthesis of (S)-5,5,5,5′,5′,5′-hexafluoroleucine
Zhang, C
Ludin, C
Eberle, MK
Stoeckli-Evans, H
Keese, R
HELVETICA CHIMICA ACTA, 1998, 81 (01) : 174 - 181
[37] A SAT-Based Approach for Solving the Modal Logic S5-Satisfiability Problem
Caridroit, Thomas
Lagniez, Jean-Marie
Le Berre, Daniel
de Lima, Tiago
Montmirail, Valentin
THIRTY-FIRST AAAI CONFERENCE ON ARTIFICIAL INTELLIGENCE, 2017, : 3864 - 3870
[38] Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one
Plourde, Guy L.
Scully, Thomas W.
MOLECULES, 2013, 18 (01) : 1174 - 1180
[39] Short diastereoselective synthesis of (2S,5R)-5-hydroxypip-ecolic acid and 6-substituted derivatives.
Blaauw, RH
Botman, PNM
Broxterman, QB
Schoemaker, HE
Rutjes, FPJT
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U533 - U533
[40] Insight into mechanisms of 3′-5′ exonuclease activity and removal of bulky 8,5′-cyclopurine adducts by apurinic/apyrimidinic endonucleases
Mazouzi, Abdelghani
Vigouroux, Armelle
Aikeshev, Bulat
Brooks, Philip J.
Saparbaev, Murat K.
Morera, Solange
Ishchenko, Alexander A.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2013, 110 (33) : E3071 - E3080

← 1 2 3 4 5 →