An improved phosphoramidite approach for the chemical synthesis of 3′,5′-cyclic diguanylic acid

Grajkowski, Andrzej; Takáhashi, Mayumí; Kaczyński, Tomasz; Srivastava, Suresh C.; Beaucage, Serge L.

doi:10.1016/j.tetlet.2019.01.006

Cited by 6 publications

(9 citation statements)

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“…Such a limitation has prompted the development of an improved chemical synthesis of c‐di‐GMP from phosphoramidite intermediates (Grajkowski et al., ). This improved synthesis is based on the unprecedented 5′‐ O ‐formylation of a commercial guanosine ribonucleoside (Srivastava, Pandey, Srivastava, & Bajpai, ; Srivastava, Pandey, Srivastava, & Bajpai, ), which had its 2′‐ and 3′‐hydroxyl functions protected with a tert ‐butyldimethylsilyl and a 4,4′‐dimethoxytrityl group, respectively; the exocyclic amine of the guanine moiety had been protected with a traditional isobutyryl group.…”

Section: Commentarymentioning

confidence: 99%

“…DMTr, 4,4′‐dimethoxytrityl; TBDMS, tert ‐butyldimethylsilyl; Gua ibu , N 2 ‐isobutyrylguanine. (Reprinted from Grajkowski et al., with permission from Elsevier. )…”

Section: Commentarymentioning

confidence: 99%

“…Such a limitation has prompted the development of an improved chemical synthesis of c-di-GMP from phosphoramidite intermediates (Grajkowski et al, 2019). This improved synthesis is based on the unprecedented 5 -O-formylation of a commercial guanosine ribonucleoside (Srivastava, Pandey, Grajkowski et al…”

Section: Background Informationmentioning

confidence: 99%

“…With the intent of providing novice experimenters with comprehensive information on the work recently published in the literature (Grajkowski, Takahashi, Kaczyński, Srivastava, & Beaucage, ), figures and textual materials have been taken from this article and adapted into step‐by‐step procedures to facilitate reproduction of the original work; this resulted in unavoidable but necessary circumstantial similarities.…”

Section: Introductionmentioning

confidence: 99%

“…Gua ibu , N 2 -isobutyrylguanine; DMTr, 4,4 -dimethoxytrityl; TBDMS, tert-butyldimethylsilyl; t-BuOOH, tert-butyl hydroperoxide. (Reprinted fromGrajkowski et al, 2019 with permission from Elsevier.) Grajkowski et al…”

mentioning

confidence: 99%

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An Improved Strategy for the Chemical Synthesis of 3′,5′‐Cyclic Diguanylic Acid

Grajkowski

Takáhashi

Kaczyński

et al. 2019

CP Nucleic Acid Chemistry

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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.

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Section: Commentarymentioning

confidence: 99%

“…DMTr, 4,4′‐dimethoxytrityl; TBDMS, tert ‐butyldimethylsilyl; Gua ibu , N 2 ‐isobutyrylguanine. (Reprinted from Grajkowski et al., with permission from Elsevier. )…”

Section: Commentarymentioning

confidence: 99%

Section: Background Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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