Synthesis of cyclic bis(3′-5′)diguanylic acid (c-di-GMP) analogs

被引：28

作者：

Hyodo, M

Sato, Y

Hayakawa, Y ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Informat Sci Human Informat, Nagoya, Aichi 4648601, Japan

[2] Nagoya Univ, CREST JST, Nagoya, Aichi 4648601, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 13期

基金：

日本科学技术振兴机构;

关键词：

nucleotides; phosphoramidites; cyclization; c-Di-GMP;

D O I：

10.1016/j.tet.2006.01.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper reports the synthesis of cyclic bis(3'-5)diguanylic acid (c-di-GMP) analogs, including the monophosphorothioic acid of c-di-GMP (c-GpGps), cyclic bis(3'-5')guanylic/adenylic acid (c-GpAp), and cyclic bis(3'-5)guanylic/inosinic acid (c-Gplp). These compounds are expected to be important, both in elucidating the mechanism of bioactive c-di-GMP and in designing and creating new bioactive c-di-GMP-related artificial derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

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收藏

页码：3089 / 3094

页数：6

相关论文

共 27 条

[1] THE NOVEL CYCLIC DINUCLEOTIDE 3'-5'-CYCLIC-DIGUANYLIC ACID BINDS TO P21(RAS) AND ENHANCES DNA-SYNTHESIS BUT NOT CELL REPLICATION IN THE MOLT 4 CELL-LINE [J].

AMIKAM, D ;

STEINBERGER, O ;

SHKOLNIK, T ;

BENISHAI, Z .

BIOCHEMICAL JOURNAL, 1995, 311 :921-927

[2] STEREOSELECTIVE SYNTHESIS OF CYCLIC DINUCLEOTIDE PHOSPHOROTHIOATES [J].

BATTISTINI, C ;

FUSTINONI, S ;

BRASCA, MG ;

BORGHI, D .

TETRAHEDRON, 1993, 49 (05) :1115-1132

[3] 3',5'-cyclic diguanylic acid reduces the virulence of biofilm-forming Staphylococcus aureus strains in a mouse model of mastitis infection [J].

Brouillette, E ;

Hyodo, M ;

Hayakawa, Y ;

Karaolis, DKR ;

Malouin, F .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2005, 49 (08) :3109-3113

[4] ONE POT SOLUTION SYNTHESIS OF CYCLIC OLIGODEOXYRIBONUCLEOTIDES [J].

CAPOBIANCO, ML ;

CARCURO, A ;

TONDELLI, L ;

GARBESI, A ;

BONORA, GM .

NUCLEIC ACIDS RESEARCH, 1990, 18 (09) :2661-2669

[5] SOLID-PHASE SYNTHESIS OF THE 5'-1/2 OF THE INITIATOR TRANSFER-RNA FROM B-SUBTILIS [J].

CHAIX, C ;

DUPLAA, AM ;

MOLKO, D ;

TEOULE, R .

NUCLEIC ACIDS RESEARCH, 1989, 17 (18) :7381-7393

[6] PEG-SUPPORTED SYNTHESIS OF CYCLIC OLIGODEOXYRIBONUCLEOTIDES [J].

DENAPOLI, L ;

MESSERE, A ;

MONTESARCHIO, D ;

PICCIALLI, G ;

SANTACROCE, C ;

BONORA, GM .

NUCLEOSIDES & NUCLEOTIDES, 1993, 12 (01) :21-30

[7] ARYLSULFONYL CHLORIDES IN THE PRESENCE OF N-METHYLIMIDAZOLE AS EFFICIENT CONDENSING REAGENTS IN PHOSPHOTRIESTER OLIGONUCLEOTIDE SYNTHESIS [J].

EFIMOV, VA ;

REVERDATTO, SV ;

CHAKHMAKHCHEVA, OG .

TETRAHEDRON LETTERS, 1982, 23 (09) :961-964

[8] Making cyclic RNAs easily available [J].

Frieden, M ;

Grandas, A ;

Pedroso, E .

CHEMICAL COMMUNICATIONS, 1999, (16) :1593-1594

[9] SYNTHESIS AND RESTRICTED CONFORMATION OF 3',5'-O-(DI-TERT-BUTYLSILANEDIYL)RIBONUCLEOSIDES [J].

FURUSAWA, K ;

UENO, K ;

KATSURA, T .

CHEMISTRY LETTERS, 1990, (01) :97-100

[10] CHEMICAL SYNTHESIS OF A BIOLOGICALLY-ACTIVE NATURAL TRANSFER-RNA WITH ITS MINOR BASES [J].

GASPARUTTO, D ;

LIVACHE, T ;

BAZIN, H ;

DUPLAA, AM ;

GUY, A ;

KHORLIN, A ;

MOLKO, D ;

ROGET, A ;

TEOULE, R .

NUCLEIC ACIDS RESEARCH, 1992, 20 (19) :5159-5166