Solid phase glycosidation of oligonucleotides

被引：26

作者：

Adinolfi, M ^{[1
]}

Barone, G ^{[1
]}

De Napoli, L ^{[1
]}

Guariniello, L ^{[1
]}

Iadonisi, A ^{[1
]}

Piccialli, G ^{[1
]}

机构：

[1] Univ Naples, Dept Organ & Biol Chem, I-80134 Naples, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 13期

关键词：

solid-phase synthesis; nucleosides; oligonucleotides; glycosidation;

D O I：

10.1016/S0040-4039(99)00228-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

CPG-bound nucleosides (deoxyguanosine excepted) can be stereoselectively glycosylated in high yield at their 5'-hydroxyl by a "disarmed" trichloroacetimidate donor in the presence of stoichiometric amounts of TMSOTf (5 eq.) and in short reaction times. These results allowed the solid-phase synthesis of an oligonucleotide functionalized at both ends with sugar residues. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2607 / 2610

页数：4

共 25 条

[1] Solid phase synthesis of oligosaccharides
Adinolfi, M
Barone, G
DeNapoli, L
Iadonisi, A
Piccialli, G
[J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 5007 - 5010
[2] Use of controlled pore glass in solid phase oligosaccharide synthesis. Application to the semiautomated synthesis of a glyconucleotide conjugate
Adinolfi, M
Barone, G
De Napoli, L
Iadonisi, A
Piccialli, G
[J]. TETRAHEDRON LETTERS, 1998, 39 (14) : 1953 - 1956
[3] SYNTHESIS OF MONOMANNOSIDE AND DIMANNOSIDE PHOSPHORAMIDITE DERIVATIVES FOR SOLID-PHASE CONJUGATION TO OLIGONUCLEOTIDES
AKHTAR, S
ROUTLEDGE, A
PATEL, R
GARDINER, JM
[J]. TETRAHEDRON LETTERS, 1995, 36 (40) : 7333 - 7336
[4] A STRATEGY FOR THE SOLID-PHASE SYNTHESIS OF OLIGOSACCHARIDES
DANISHEFSKY, SJ
MCCLURE, KF
RANDOLPH, JT
RUGGERI, RB
[J]. SCIENCE, 1993, 260 (5112) : 1307 - 1309
[5] FRASERREID B, 1992, SYNLETT, P927
[6] GAIT MJ, 1984, OLIGONUCLEOTIDE SYNT
[7] Heckel A, 1998, SYNLETT, P171
[8] Solid-phase synthesis of 6-deoxyoligosaccharides
Hunt, JA
Roush, WR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (41) : 9998 - 9999
[9] Parallel synthesis and screening of a solid phase carbohydrate library
Liang, R
Yan, L
Loebach, J
Ge, M
Uozumi, Y
Sekanina, K
Horan, N
Gildersleeve, J
Thompson, C
Smith, A
Biswas, K
Still, WC
Kahne, D
[J]. SCIENCE, 1996, 274 (5292) : 1520 - 1522
[10] Manabe S, 1998, SYNLETT, P628

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