Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)

被引：15

作者：

Fujino, Tomoko ^{[1
]}

Tsunaka, Nobuhide ^{[1
]}

Guillot-Nieckowski, Marine ^{[2
]}

Nakanishi, Waka ^{[1
]}

Iwamoto, Takeaki ^{[1
]}

Nakamura, Eiichi ^{[2
]}

Isobe, Hiroyuki ^{[1
]}

机构：

[1] Tohoku Univ, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Univ Tokyo, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 15期

关键词：

Transglycosylation; Artificial deoxyribonucleoside; Puckering conformation; NUCLEOSIDE SYNTHESIS; CONFORMATION;

D O I：

10.1016/j.tetlet.2010.02.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5'-position and azido group at the pseudo-3'-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2036 / 2038

页数：3

共 50 条

[41] Synthesis and glycosidase inhibition properties of triazole-linked calixarene-iminosugar clusters
Marra, Alberto
Zelli, Renaud
D'Orazio, Giuseppe
La Ferla, Barbara
Dondoni, Alessandro
TETRAHEDRON, 2014, 70 (49) : 9387 - 9393
[42] Click Synthesis of Triazole-Linked Polyazamacrocycles through Selective Isopimaric Acid Transformations
Gromova, Marya A.
Kharitonov, Yurii, V
Rybalova, Tatyana, V
Shults, Elvira E.
MACROHETEROCYCLES, 2021, 14 (01): : 105 - 111
[43] Synthesis, Affinity for Complementary RNA and DNA, and Enzymatic Stability of Triazole-Linked Locked Nucleic Acids (t-LNAs)
Kumar, Pawan
Truong, Lynda
Baker, Ysobel Ruth
El-Sagheer, Afaf Helmy
Brown, Tom
ACS OMEGA, 2018, 3 (06): : 6976 - 6987
[44] Efficient preparation and properties of triazole-linked corannulene derivatives
Stuparu, Mihaiela C.
TETRAHEDRON, 2012, 68 (18) : 3527 - 3531
[45] Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds
Guantai, Eric M.
Ncokazi, Kanyile
Egan, Timothy J.
Gut, Jiri
Rosenthal, Philip J.
Smith, Peter J.
Chibale, Kelly
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (23) : 8243 - 8256
[46] Efficient synthesis of some unsaturated [1,2,3]-triazole-linked glycoconjugates
de Oliveira, Ronaldo N.
Sinou, Denis
Srivastava, Rajendra M.
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2006, 25 (05) : 407 - 425
[47] "Click-fluors": triazole-linked saccharide sensors
Zhai, Wenlei
Chapin, Brette M.
Yoshizawa, Akina
Wang, Hui-Chen
Hodge, Stephen A.
James, Tony D.
Anslyn, Eric V.
Fossey, John S.
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (08): : 918 - 928
[48] Synthesis of New C-2 Triazole-Linked Analogs of Triterpenoid Pentacyclic Saponins
A. Yu. Spivak
Z. R. Galimshina
D. A. Nedopekina
V. N. Odinokov
Chemistry of Natural Compounds, 2018, 54 : 315 - 323
[49] Divalent Triazole-Linked Carbohydrate Mimetics: Synthesis by Click Chemistry and Evaluation as Selectin Ligands
Salta, Joana
Reissig, Hans-Ulrich
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (28) : 4361 - 4370
[50] Design, synthesis and fluorescence property evaluation of blue emitting triazole-linked chromene peptidomimetics
Mohan, T. Jency
Bahulayan, D.
MOLECULAR DIVERSITY, 2017, 21 (03) : 585 - 596

← 1 2 3 4 5 →