Oligonucleotide synthesis using the 2-(levulinyloxymethyl)-5-nitrobenzoyl group for the 5′-position of nucleoside 3′-phosphoramidite derivatives

被引：10

作者：

Kamaike, K ^{[1
]}

Takahashi, H ^{[1
]}

Morohoshi, K ^{[1
]}

Kataoka, N ^{[1
]}

Kakinuma, T ^{[1
]}

Ishido, Y ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Lab Pharmaceut Chem, Hachioji, Tokyo 1920392, Japan

来源：

ACTA BIOCHIMICA POLONICA | 1998年 / 45卷 / 04期

关键词：

2-(levulinyloxymethyl)-5-nitrobenzoyl group; 2-(levulinyloxymethyl)benzoyl group; base-labile protecting group; solid-phase oligonucleotide synthesis; CpCpA terminus triplet of tRNAs; N-15-labeled oligoribonucleotide; 2 '-O-(beta-D-ribofuranosyl)adenosine;

D O I：

10.18388/abp.1998_4354

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：

A comparative study on the utility of 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) and 2-(levulinyloxymethyl)benzoyl (LMBz) protecting groups for the 5'-positions of nucleoside 3'-phosphoramidite derivatives in the oligonucleotide synthesis is presented in terms of the syntheses of TpTpT, TpTpTpT, and UpCpApGpUpUpGpG. In addition we describe the synthesis, using the LMNBz protecting group of the CpCpA terminus triplet of tRNAs bearing exocyclic amino groups with N-15-labeling, and the trimer Gp[A*]pG containing 2'-O-(beta-D-ribofuranosyl)adenosine ([A*]), the latter of which is found at position 64 in the yeast initiator tRNA(Met).

引用

页码：949 / 976

页数：28

共 50 条

[21] NUCLEOSIDE STUDIES .4. SYNTHESIS OF 2',5'-DIDEOXYCYTIDINES AND OTHER DERIVATIVES OF 2'-DEOXYCYTIDINE
BENZ, E
ELMORE, NF
GOLDMAN, L
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09): : 3067 - &
[22] Synthesis and P2Y receptor activity of nucleoside 5′-phosphonate derivatives
Cosyn, Liesbet
Van Calenbergh, Serge
Joshi, Bhalchandra V.
Ko, Hyojin
Carter, Rhonda L.
Harden, T. Kendall
Jacobson, Kenneth A.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (11) : 3002 - 3005
[23] Synthesis and herbicidal activities of 2-(5-isoxazolyloxy)acetamide derivatives
Kai, H
Horita, Y
Miki, N
Ide, K
Takase, A
JOURNAL OF PESTICIDE SCIENCE, 1998, 23 (03): : 255 - 261
[24] Synthesis of oligonucleotides containing 2′-deoxyisoguanosine and 2′-deoxy-5-methylisocytidine using phosphoramidite chemistry
Jurczyk, SC
Kodra, JT
Rozzell, JD
Benner, SA
Battersby, TR
HELVETICA CHIMICA ACTA, 1998, 81 (05) : 793 - 811
[25] Synthesis and conformation of 3'-O,4'-C-methyleneribonucleosides, novel bicyclic nucleoside analogues for 2',5'-linked oligonucleotide modification
Obika, S
Morio, K
Nanbu, D
Imanishi, T
CHEMICAL COMMUNICATIONS, 1997, (17) : 1643 - 1644
[26] Synthesis of Oligonucleotides Containing 2'-Deoxyisoguanosine and 2'-Deoxy-5-methylisocytidine Using Phosphoramidite Chemistry
Helv Chim Acta, 5 (793):
[27] Practical and reliable synthesis of 2′,3′,5′,5"-tetradeuterated uridine derivatives
Miyamoto, Noriko
Ohno, Hiroki
Kitamura, Yoshiaki
Park, Kwihwan
Sawama, Yoshinari
Sajiki, Hironao
Kitade, Yukio
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2020, 39 (1-3): : 236 - 244
[28] Synthesis of 2′-deoxyribonucleoside 5′-phosphoramidites:: New building blocks for the inverse (5′-3′)-oligonucleotide approach
Wagner, T
Pfleiderer, W
HELVETICA CHIMICA ACTA, 2000, 83 (08) : 2023 - 2035
[29] SYNTHESIS OF 5'-MODIFIED NUCLEOSIDE ANALOGS OF PYRIDON-(2) AND 5,6-DIPHENYLPYRIDAZON-(3)
PISCHEL, H
WAGNER, G
PHARMAZIE, 1970, 25 (01): : 45 - &
[30] LITHIATION OF AN IMIDAZOLE NUCLEOSIDE AT THE C-5 POSITION - SYNTHESIS OF 3-DEAZAGUANOSINE FROM URIDINE
TANAKA, H
HIRAYAMA, M
MATSUDA, A
MIYASAKA, T
UEDA, T
CHEMISTRY LETTERS, 1985, (05) : 589 - 592

← 1 2 3 4 5 →