Nucleotides part XXXII. Synthesis of a dithymidine dinucleotide containing a 3′: 5′-internucleotidic linkage

Michelson, A.M.; Todd, A. R.

doi:10.1039/jr9550002632

Cited by 150 publications

(77 citation statements)

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“…The combined filtrates were concentrated and dried in vacuo, and crude materials 5a-h were submitted to silica gel column chromatography (DCM/EtOAc, 5:3). (11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30) equiv.) at 80-90°C under an atmosphere of argon.…”

Section: ј-Deoxyuridin-5ј-yl)phosphates 5a-h: Oo-dialkyl-nn-diisopro-mentioning

confidence: 99%

“…[24] This method was also used in the synthesis of dinucleotide, wherein the bridging phosphate is a triester. [30] The phosphoramidite method is a versatile method to introduce phosphates as diesters into alcohols to establish phosphoric acid triesters via intermediate phosphites. In this way, lipophilic phosphates like cholesteryl phosphates or long-chain glycerol ether phosphates were transferred as well.…”

Section: Synthesis Of Lipophilic Nucleosidesmentioning

confidence: 99%

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Nucleosides with 5′‐Fixed Lipid Groups – Synthesis and Anchoring in Lipid Membranes

Brodersen

Kaczmarek

et al. 2007

Eur J Org Chem

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Section: ј-Deoxyuridin-5ј-yl)phosphates 5a-h: Oo-dialkyl-nn-diisopro-mentioning

confidence: 99%

Section: Synthesis Of Lipophilic Nucleosidesmentioning

confidence: 99%

Nucleosides with 5′‐Fixed Lipid Groups – Synthesis and Anchoring in Lipid Membranes

Brodersen

Kaczmarek

et al. 2007

Eur J Org Chem

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“…Virtually, all gene synthesis methods are based on oligonucleotide synthesis causing many technical as well as cost implications. The chemical synthesis of short single strand DNA dates back to 1955 and provided the directed chemical synthesis of a dithymidinyl nucleotide [85]. Over the decades oligonucleotide chemistry was improved, but it took until the beginning of the 1980s when the phosphoramidite approach and solid phase synthesis allowed the development of routine oligonucleotide synthesis, as we know it today.…”

Section: Oligonucleotide Synthesis-creating Your Templatementioning

confidence: 99%

Rationales of Gene Design andDe NovoGene Construction

Graf¹,

Schoedl²,

Wagner

2009

Systems Biology and Synthetic Biology

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“…phosphate triester method, which served as the starting point for oligonucleotide synthesis (16). Khorana and colleagues then developed the phosphodiester method (17), which was followed by H-phosphonate and phosphoramidite approaches (18).…”

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confidence: 99%

Combined Approaches to Site-Specific Modification of RNA

2008

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Both natural and unnatural modifications in RNA are of interest to biologists and chemists. More than 100 different analogs of the four standard RNA nucleosides have been identified in nature. Unnatural modifications are useful for structure and mechanistic studies of RNA. This Review highlights chemical, enzymatic, and combined (semisynthesis) approaches to generate sitespecifically modified RNAs. The availability of these methods for site-specific modifications of RNAs of all sizes is important in order to study the relationships between RNA chemical composition, structure, and function.RNAs undergo specific post-transcriptional modification by a wide variety of enzymes and ribonucleoprotein complexes (1,2). More than 100 different modifications of the four standard RNA nucleosides, adenosine, cytidine, guanosine, and uridine, have been identified (3). Examples from each of the four major categories of base isomerization, base modification, sugar modification, and hypermodification are shown in Figure 1, panel a. Similarly, a large number of unnatural modifications have been synthesized and used for structure and mechanistic studies of RNA (4-6). A few examples are shown in Figure 1, panel b (7-10). Natural modified nucleotides are often found in the functionally important regions of RNA, such as the peptidyl transferase center of ribosomal RNA (rRNA), the anticodon loop of transfer RNAs, or the branch site of spliceosomal . Several modifications, such as pseudouridine (14), have been known for almost 50 years. Their locations in natural RNAs can, in some cases, be highly conserved; yet, our understanding of their biological roles is still incomplete (15). Through a combination of biological, chemical, and biophysical approaches, much can be learned regarding the roles of modified nucleotides. Similarly, the incorporation of unnatural modifications may be useful in order to study the biological roles and functions of RNA (5).In a number of cases, the enzymes or small nucleolar RNAs (snoRNAs) that are responsible for site-specific RNA modification have been identified (2). Knock-out studies of the individual modifying enzymes or snoRNAs then allow the function of the modification to be deduced. In cases where the enzymes are not known, or the modification is not a natural one, alternative approaches must be considered. Over the past several decades, several chemical methods have been developed to study the effects of modifications in small RNA model systems. These studies have led to newer, more powerful approaches that allow site-specific modification of large RNAs, reconstitution into biological systems, and studies of RNA structure and function. Chemical SynthesisChemical synthesis of RNA allows for site-selective incorporation of modified nucleotides. Five decades ago, Michelson and coworkers synthesized a thymidylate dinucleotide by the *Corresponding author csc@chem.wayne.edu. Figure 2): i) coupling at the 5′ site with a protected phosphoramidite, ii) capping of the unreacted 5′-hydroxyl groups, ...

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Nucleotides part XXXII. Synthesis of a dithymidine dinucleotide containing a 3′: 5′-internucleotidic linkage

Cited by 150 publications

References 0 publications

Nucleosides with 5′‐Fixed Lipid Groups – Synthesis and Anchoring in Lipid Membranes

Nucleosides with 5′‐Fixed Lipid Groups – Synthesis and Anchoring in Lipid Membranes

Rationales of Gene Design andDe NovoGene Construction

Combined Approaches to Site-Specific Modification of RNA

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