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

[1] Oligonucleotide synthesis by the use of a 2-(levulinyloxymethyl)-5-nitrobenzoyl group as the novel base-labile protecting group for the 5'-hydroxyl groups of ribonucleoside and 2'-deoxyribonucleoside 3'-phosphoramidites
Kamaike, K.
Takahashi, H.
Kakinuma, T.
Morohoshi, K.
Tetrahedron Letters, 38 (39):
[2] Oligonucleotide synthesis by the use of a 2-(levulinyloxymethyl)-5-nitrobenzoyl group as the novel base-labile protecting group for the 5'-hydroxyl groups of ribonucleoside and 2'-deoxyribonucleoside 3'-phosphoramidites
Kamaike, K
Takahashi, K
Kakinuma, T
Morohoshi, K
Ishido, Y
TETRAHEDRON LETTERS, 1997, 38 (39) : 6857 - 6860
[3] 6-(Levulinyloxymethyl)-3-methoxy-2-nitrobenzoyl and 2-(levulinyloxymethyl)-5-methoxy-4-nitrobenzoyI groups as novel base-labile groups for 5′-hydroxy protection in solid-phase oligonucleotide synthesis
Kamaike, K
Namiki, T
Kawashima, E
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (04): : 469 - 487
[4] Synthesis of monomers bearing at the 2′-position cyanomethoxycarbonyl group for phosphoramidite oligonucleotide synthesis
Vasilyeva, SV
Abramova, TV
Silnikov, VN
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2004, 23 (6-7): : 993 - 998
[5] SYNTHESIS OF ADENOSINE DERIVATIVES WITH CARBOXYALKYL SIDE CHAIN AT 2',3'OR 5'POSITION
Zeng Li SONG Jun Dong ZHANG Li He ZHANG School of Pharmaceutical Sciences
Chinese Chemical Letters, 1993, (12) : 1053 - 1056
[6] Synthesis of Substituted Cy5 Phosphoramidite Derivatives and Their Incorporation into Oligonucleotides Using Automated DNA Synthesis
Meares, Adam
Susumu, Kimihiro
Mathur, Divita
Lee, Sang Ho
Mass, Olga A.
Lee, Jeunghoon
Pensack, Ryan D.
Yurke, Bernard
Knowlton, William B.
Melinger, Joseph S.
Medintz, Igor L.
ACS OMEGA, 2022, 7 (13): : 11002 - 11016
[7] New approach to synthesis of derivatives of 2-(5-hydroxybenzofuryl-3)naphthofurans
Mukhanova T.I.
Lykova O.A.
Alekseeva L.M.
Granik V.G.
Chemistry of Heterocyclic Compounds, 1998, 34 (6) : 651 - 657
[8] New approach to synthesis of 2-(5-hydroxybenzofuryl-3)naphthofuran derivatives
Mukhanova, TI
Lykova, OA
Alekseeva, LM
Granik, VG
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (06): : 748 - 755
[9] Synthesis and properties of nucleoside derivatives acylated by chemically stable 2-(trimethylsilyl)benzoyl group
Yamada, Ken
Taguchi, Haruhiko
Ohkubo, Akihiro
Seio, Kohji
Sekine, Mitsuo
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (16) : 5928 - 5932
[10] Synthesis of 2′-[2-(5-benzyloxyindolyl)]propylamine derivatives
Marco, JL
Martín, G
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (04) : 921 - 926

← 1 2 3 4 5 →