An improved synthesis of guanosine TNA phosphoramidite for oligonucleotide synthesis

被引：0

作者：

Majumdar, Biju ^{[1
]}

Sarma, Daisy ^{[1
]}

Lee, Erica M. ^{[1
]}

Setterholm, Noah A. ^{[1
]}

Chaput, John C. ^{[1
,2
,3
,4
]}

机构：

[1] Univ Calif Irvine, Dept Pharmaceut Sci, Irvine, CA 92697 USA

[2] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

[3] Univ Calif Irvine, Dept Mol Biol & Biochem, Irvine, CA 92697 USA

[4] Univ Calif Irvine, Dept Chem & Biomol Engn, Irvine, CA USA

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2024年

关键词：

Threose nucleic acid; phosphoramidites; coupling efficiency; solid-phase oligonucleotide synthesis; PROGRESS; RNA;

D O I：

10.1080/15257770.2024.2369688

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The chemical synthesis of guanosine nucleosides generates both the N9 and N7 regioisomers, which require careful separation to obtain the desired N9 isomer. To preferentially obtain the N9 isomer, a bulky diphenylcarbamoyl (DPC) group can be installed at the O6 position of guanine. However, installation of the DPC group presents a challenging task due to low solubility of the N-acetyl protected guanine. Here we report the usage of commercially available 2-amino-6-chloro purine as a new strategy that offers a more efficient route to the synthesis of the guanine phosphoramidite of threose nucleic acid (TNA).

引用

页数：12

共 50 条

[31] DIETHOXY N,N-DIISOPROPYL PHOSPHORAMIDITE AS AN IMPROVED CAPPING REAGENT IN THE SYNTHESIS OF OLIGONUCLEOTIDES USING PHOSPHORAMIDITE CHEMISTRY
YU, D
TANG, JY
IYER, RP
AGRAWAL, S
TETRAHEDRON LETTERS, 1994, 35 (46) : 8565 - 8568
[32] SYNTHESIS OF PHOSPHOLIPIDS BY PHOSPHORAMIDITE METHODOLOGY
MCGUIGAN, C
SWORDS, B
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03): : 783 - 787
[33] Phosphoramidite approach for the synthesis of cardiolipin
Krishna, UM
Ahmad, MU
Ahmad, I
TETRAHEDRON LETTERS, 2004, 45 (10) : 2077 - 2079
[34] The mechanism of the phosphoramidite synthesis of polynucteotides
Russell, Mark A.
Laws, Andrew R.
Atherton, John H.
Page, Michael I.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (18) : 3270 - 3275
[35] Expansion of Phosphoramidite Chemistry in Solid-Phase Oligonucleotide Synthesis: Rapid 3′-Dephosphorylation and Strand Cleavage
Yamamoto, Kazuki
Fuchi, Yasufumi
Ito, Yuta
Hari, Yoshiyuki
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05): : 2726 - 2734
[36] The use of 6-carboxynaphthofluorescein phosphoramidite in the automated synthesis of quencher-dye oligonucleotide probes (QDOPs)
Vu, Huynh
Majlessi, Mehrdad
Adelpour, Dennis
Russell, James
TETRAHEDRON LETTERS, 2009, 50 (07) : 737 - 740
[37] An improved phosphoramidite approach for the chemical synthesis of 3′,5′-cyclic diguanylic acid
Grajkowski, Andrzej
Takahashi, Mayumi
Kaczynski, Tomasz
Srivastava, Suresh C.
Beaucage, Serge L.
TETRAHEDRON LETTERS, 2019, 60 (05) : 452 - 455
[38] IMPROVEMENTS IN THE PHOSPHORAMIDITE PROCEDURE FOR THE SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES
DORPER, T
WINNACKER, EL
NUCLEIC ACIDS RESEARCH, 1983, 11 (09) : 2575 - 2584
[39] Improved synthesis of trinucleotide phosphoramidites for generation of randomized oligonucleotide libraries
Yagodkin, Andrey
Azhayev, Alex
Roivainen, Jarkko
Antopolsky, Maxim
Kayushin, Alexei
Korosteleva, Maria
Miroshnikov, Anatoly
Randolph, John
Mackie, Hugh
CHEMISTRY OF NUCLEIC ACID COMPONENTS, 2008, 10 : 309 - 310
[40] Improved synthesis of trinucleotide phosphoramidites and generation of randomized oligonucleotide libraries
Yagodkin, Andrey
Azhayev, Alex
Roivainen, Jarkko
Antopolsky, Maxim
Kayushin, Alexei
Korosteleva, Maria
Miroshnikov, Anatoly
Randolph, John
Mackie, Hugh
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (05): : 473 - 497

← 1 2 3 4 5 →