New approach for the synthesis of c-di-GMP and its analogues

被引：30

作者：

Amiot, Nicolas ^{[1
]}

Heintz, Karine ^{[1
]}

Giese, Bernd ^{[1
]}

机构：

[1] Univ Basel, Inst Organ Chem, CH-4056 Basel, Switzerland

来源：

SYNTHESIS-STUTTGART | 2006年 / 24期

关键词：

c-di-GMP; nucleotide; cyclization; nucleobases; phosphotriester methodology;

D O I：

10.1055/s-2006-950361

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of cyclic bis(3'-5')diguanylic acid (c-di-GMP) by using a new flexible approach is reported. The flexibility of the method is exemplified by the synthesis of base-modified analogues that will find applications in the elucidation of c-di-GMP biological modes of action.

引用

页码：4230 / 4236

页数：7

共 25 条

[1] PilZ domain is part of the bacterial c-di-GMP binding protein [J].

Amikam, D ;

Galperin, MY .

BIOINFORMATICS, 2006, 22 (01) :3-6

[2] The phosphodiesterase activity of the HmsP EAL domain is required for negative regulation of biofilm formation in Yersinia pestis [J].

Bobrov, AG ;

Kirillina, O ;

Perry, RD .

FEMS MICROBIOLOGY LETTERS, 2005, 247 (02) :123-130

[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] Structural basis of activity and allosteric control of diguanylate cyclase [J].

Chan, C ;

Paul, R ;

Samoray, D ;

Amiot, NC ;

Giese, B ;

Jenal, U ;

Schirmer, T .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (49) :17084-17089

[5]

DattaGupta A, 1996, SYNLETT, P69

[6] Synthesis of cyclic bis(3′-5′)diguanylic acid (c-di-GMP) analogs [J].

Hyodo, M ;

Sato, Y ;

Hayakawa, Y .

TETRAHEDRON, 2006, 62 (13) :3089-3094

[7] An improved method for synthesizing cyclic bis(3′-5′)diguanylic acid (c-di-GMP) [J].

Hyodo, M ;

Hayakawa, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (11) :2089-2093

[8] AN EXTREMELY SIMPLE, CONVENIENT, AND SELECTIVE METHOD FOR ACETYLATING PRIMARY ALCOHOLS IN THE PRESENCE OF SECONDARY ALCOHOLS [J].

ISHIHARA, K ;

KURIHARA, H ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3791-3793

[9] Signal transduction mechanisms in Caulobacter crescentus development and cell cycle control [J].

Jenal, U .

FEMS MICROBIOLOGY REVIEWS, 2000, 24 (02) :177-191

[10] EFFICIENT REGIOSELECTIVE SYNTHESIS OF GUANOSINE ANALOGS [J].

JENNY, TF ;

BENNER, SA .

TETRAHEDRON LETTERS, 1992, 33 (44) :6619-6620

← 1 2 3 →