Evidence map›Paper›PMID 30970180›Full record

ArticleCurrent protocols in nucleic acid chemistry2019

An Improved Strategy for the Chemical Synthesis of 3',5'-Cyclic Diguanylic Acid.

Andrzej Grajkowski, Mayumi Takahashi, Tomasz Kaczyński, Suresh C Srivastava, Serge L Beaucage

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Current protocols in nucleic acid chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

  1. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

5 authors.

Andrzej GrajkowskiLaboratory of Biological Chemistry, Food and Drug Administration, Silver Spring, Maryland.
Mayumi TakahashiLaboratory of Biological Chemistry, Food and Drug Administration, Silver Spring, Maryland.
Tomasz KaczyńskiLaboratory of Biological Chemistry, Food and Drug Administration, Silver Spring, Maryland.
Suresh C SrivastavaChemGenes Corporation, Wilmington, Massachusetts.
Serge L BeaucageLaboratory of Biological Chemistry, Food and Drug Administration, Silver Spring, Maryland.

Funding

Intramural FDA HHS FD999999
6 · The paper itself

Abstract

The physiological functions of c-di-GMP and its involvement in many key processes led to its recognition as a major and ubiquitous bacterial second messenger. Aside from being a bacterial signaling molecule, c-di-GMP is also an immunostimulatory molecule capable of inducing innate and adaptive immune responses through maturation of immune mammalian cells. Given the broad biological functions of c-di-GMP and its potential applications as a nucleic-acid-based drug, the chemical synthesis of c-di-GMP has drawn considerable interest. An improved phosphoramidite approach to the synthesis of c-di-GMP is reported herein. The synthetic approach is based on the use of a 5'-O-formyl protecting group, which can be rapidly and chemoselectively cleaved from a key dinucleotide phosphoramidite intermediate to enable a cyclocondensation reaction leading to a fully protected c-di-GMP product in a yield ∼80%. The native c-di-GMP is isolated, after complete deprotection, in an overall yield of 36% based on the commercial ribonucleoside used as starting material. © 2019 by John Wiley & Sons, Inc.

Indexed as

AmidesCyclic GMPEstersPhosphoric AcidsRibonucleosidesAmidesbis(3',5')-cyclic diguanylic acidCyclic GMPEstersphosphoramidic acidPhosphoric AcidsRibonucleosides5′-O-formyl esterchemoselective cleavagecyclocondensation reactionphosphoramidite intermediatesthermolytic phosphate protecting group

Identifiers

PMID30970180
PMCPMC6581608

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.