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C-di-GMP, analogues thereof and preparation method thereof

A technology for cyclic diguanylic acid and tert-butyldimethylsilylguanosine, which is applied in the field of synthesizing cyclic diguanylic acid and its analogues by the one-pot phosphoramidite method, and can solve the problem that deprotection cannot be carried out well , product instability, low cyclization yield, etc., to achieve good drug development prospects, cheap and easy to obtain reagents, and easy operation

Active Publication Date: 2013-12-18
PEKING UNIV
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Problems solved by technology

However, there are obvious defects in these methods: some cyclization yields are low, some conditions are severe and the product is unstable, some routes are longer, and some deprotection cannot be carried out well. These problems have limited chemical synthesis. c-di-GMP

Method used

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  • C-di-GMP, analogues thereof and preparation method thereof
  • C-di-GMP, analogues thereof and preparation method thereof
  • C-di-GMP, analogues thereof and preparation method thereof

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Embodiment Construction

[0034] All solvents, raw materials and reagents are analytically or chemically pure unless otherwise specified. The anhydrous treatment of the solvent is carried out according to a conventional method.

[0035]Instruments and methods for product separation and identification: Thin-layer chromatography silica gel GF254 (type 60) is produced by Qingdao Ocean Chemical Group Co., Ltd., column chromatography silica gel (200-300 mesh) is produced by Shanghai Shangbang Industrial Co., Ltd., imported column layer Chromatographic silica gel was produced by Merck Company in Germany; TLC was detected by 254nm ultraviolet; HR-FAB was measured by Bruker BIFLEXTMIII mass spectrometer; NMR spectrum was measured by Varian VXR-500, Bruker400, JOEL AL300 NMR; As the internal standard, the phosphorus spectrum is based on 85%H 3 PO 4 It is an external standard; HPLC uses a Gilson high-performance liquid chromatograph, and uses an Angela Venusil XBP C-18 semi-preparative column for separation. ...

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Abstract

The invention discloses a c-di-GMP and analogues thereof which have structures of a general formula I. The invention also discloses a novel preparation method-a kettle phosphoramidite method which can be used for rapidly, simply and conveniently preparing c-di-GMP compounds with high yield and low cost on a large scale and at mild conditions. The c-di-GMP is prevalent in bacteria and is a novel second messenger molecular which takes part in regulating multiple physiological functions. The research shows that the c-di-GMP and the analogues thereof can inhibit the formation of bacterium biological membranes and the multiplication of eukaryotic cells; and thereof the c-di-GMP and the analogues thereof have good medicine development prospect.

Description

technical field [0001] The present invention relates to cyclic dinucleotide compounds, in particular to cyclic diguanylic acid (c-di-GMP) and its analogues, and also to a preparation method for such compounds, in particular to the application of a one-pot phosphoramidite method to synthesize cyclic Diguanylic acid and its analogues. Background technique [0002] Cyclic diguanosine monophosphate (c-di-GMP) is a new type of second messenger molecule ubiquitous in bacteria and involved in the regulation of various physiological functions. It not only has important physiological activities, but also participates in many important biological reactions. Studies in recent years have shown that c-di-GMP and its cyclic dinucleotide analogs can inhibit the formation of bacterial biofilms and the proliferation of eukaryotic cells, so they have good prospects for drug development. [0003] However, the signal transduction mechanism of c-di-GMP is still unknown so far, mainly because it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/213C07H1/00
Inventor 杨振军邢磊陈卓王萌张礼和
Owner PEKING UNIV
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