N-levulination of nucleosides

Ogilvie, Kelvin K.; Nemer, Mona J.; Hakimelahi, G. H.; Proba, Zbigniew A.; Lucas, Marc

doi:10.1016/s0040-4039(00)87411-0

Cited by 29 publications

(10 citation statements)

References 9 publications

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“…With regard to the use of acyl (acetyl or benzoyl) protection for 2′‐OH reported in an early work, this resulted in very poor yields 4. The tert ‐butyldimethylsilyl (TBDMS) group is certainly the most commonly utilized group for 2′‐OH protection 5. Several protecting groups6, 7 have been proposed in place of TBDMS, such as triisopropylsilyloxymethyl (TOM),8 bis(2‐acetoxyethyloxy)methyl (ACE),9 tert ‐butyldithiomethyl (DTM),10 1‐(2‐cyanoethoxy)ethyl (CEE),11 2‐cyanoethoxymethyl (CEM),12, 13 2‐(4‐toluylsulfonyl)ethoxymethyl (TEM),14 and 2‐cyanoethyl [15] ; most of them, like TBDMS, are removed by fluoride ions.…”

Section: Methodsmentioning

confidence: 99%

A Base‐Labile Group for 2′‐OH Protection of Ribonucleosides: A Major Challenge for RNA Synthesis

Lavergne

Bertrand

Vasseur

et al. 2008

Chemistry A European J

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A novel methodology that disrupts the dogma “RNA synthesis is incompatible with a whole base‐labile strategy” has been developed. In this strategy (see scheme), 2′‐OH groups are protected by pivaloyloxymethyl groups, compatible with standard base‐labile protections for nucleobases and phosphates. Protecting groups are removed in a short two‐step all‐base procedure to afford RNA efficiently, rapidly, and in high purity without chain rupture or isomerization.

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Section: Methodsmentioning

confidence: 99%

A Base‐Labile Group for 2′‐OH Protection of Ribonucleosides: A Major Challenge for RNA Synthesis

Lavergne

Bertrand

Vasseur

et al. 2008

Chemistry A European J

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“…Since it is highly desirable that the 2′‐protecting groups should withstand the conditions required for the deblocking of the base residues, the standard N ‐acyl groups are incompatible with the use of the Lev group. This problem was solved by using the N ‐Lev group to protect the exocyclic amino functions of adenosine and cytidine (Ogilvie et al, ). However, the (dimethylamino)methylene (dmf) group was used for the protection of the 2‐amino function of guanosine (McBride et al, ).…”

Section: Protection Of the 2′‐hydroxy Function In The Solid‐phase Synmentioning

confidence: 99%

Recent Advances in the Chemical Synthesis of RNA

Beaucage

Reese

2009

CP Nucleic Acid Chemistry

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As a consequence largely of recent developments in RNA interference (RNAi) research, the availability of rapid and efficient methods for the chemical synthesis of RNA sequences has become a matter of considerable urgency. This unit is concerned mainly with work that has been carried out, especially in the past decade, on the design of new and improved methods of RNA synthesis. The main criteria for the choice of protecting groups for the 2'-hydroxy functions of the ribonucleoside building blocks, which is arguably the most crucial strategic decision to be made, are discussed. A number of new ether-, acetal-, orthoester-, and ester-based 2'-protecting groups are described and their application, mainly in phosphoramidite-based solid-phase synthesis, is discussed in some detail. Brief consideration is also given to solution-phase RNA synthesis, which may well prove to be of great importance if a systemic drug is developed and multikilogram quantities of synthetic RNA sequences are required.

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“…13,17,18 Vice versa, it can be quantitatively removed with hydrazine hydrate in pyridine/acetic acid, leaving the 2 0 -O-tert-butyldimethylsilyl protecting group and the succinyl linker attaching the oligonucleotide to the solid support intact. 19,20 However, the routinely used and easily removable phenoxyacetyl (PAC) groups for N-protection 21 turned out to be too labile under the conditions of hydrazinolysis. Therefore, more stable N-protecting groups were used: benzoyl for A and C, 17 and dimethylformamidine for G. 21,22 The half life of N-benzoyl protected adenosine and cytidine under the conditions of hydrazinolysis was determined to be about 3 and 5 h, respectively, while the dimethylformamidine group was stable for the time of observation.…”

Section: Synthesis Of the Branched Ribozymementioning

confidence: 99%