Synthesis and biological activity of 4-(.beta.-D-ribofuranosyl)-1,3-dihydroxybenzene (1,3-dideazauridine)

Sharma, Ram; Bobek, M.; Bloch, Alexander

doi:10.1021/jm00239a006

Cited by 15 publications

(3 citation statements)

References 16 publications

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“…In order to circumvent this problem a different strategy was followed. The known tetra-O-benzyl--ribose 10 [17] was treated with 2,4-dibenzyloxyphenyllithium to afford the addition product 11 as a 9:1 mixture of diastereoisomers; acetylation with acetic anhydride in pyridine gave O-acetyl derivative 11A. However, hydrogenolysis of 11 under the aforementioned conditions gave undesired product 9.…”

Section: Eur J Org Chem 2000 1467ϫ1482 1468mentioning

confidence: 99%

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Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

et al. 2000

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The reaction of sialyl phosphites 1, 22a‐d, 28, 39, and 45 with acyl‐protected riboside 5‐phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding β‐configured sialyl riboside monophosphates 3a,b, 24a‐d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a‐d, 30, 48, and 49 is described. Investigations with α(2‐6)‐sialyltransferase from rat liver showed that base replacement in CMP‐Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5‐, 8‐, or 9‐position of the neuraminic acid residue (25a‐d, 30, 48, 49) are tolerated.

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Section: Eur J Org Chem 2000 1467ϫ1482 1468mentioning

confidence: 99%

“…A solution of 10 [17] (3.70 g, 0.10 mmol) in dry THF (130 mL) was cooled to -70°C under nitrogen. n-Butylli-thium in n-hexane (1.6 , 6.0 mL) was added dropwise.…”

Section: 3-di-o-benzyl-4-(2345-tetra-o-benzyl-d-allo/altro-pentimentioning

confidence: 99%

Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

et al. 2000

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“…Two reports of substituted phenylribosides have been published, but these structures were not incorporated into DNA strand. 27,28 There is one report of a thiomethylindole nucleoside, designed for cross-linking purposes, which was incorporated into an oligonucleotide. 29 Nitropyrrole-and nitroindole-based nucleosides designed to serve as "universal" pairing compounds were also recently reported.…”

Section: Design Of Nucleosidesmentioning

confidence: 99%

Hydrophobic, Non-Hydrogen-Bonding Bases and Base Pairs in DNA

Schweitzer

Kool²

1995

J. Am. Chem. Soc.

267

191

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We report the properties of hydrophobic isosteres of pyrimidines and purines in synthetic DNA duplexes. Phenyl nucleosides 1 and 2 are nonpolar isosteres of the natural thymidine nucleoside, and indole nucleoside 3 is an analog of the complementary purine 2-aminodeoxyadenosine. The nucleosides were incorporated into synthetic oligodeoxynucleotides and were paired against each other and against the natural bases. Thermal denaturation experiments were used to measure the stabilities of the duplexes at neutral pH. It is found that the hydrophobic base analogs are nonselective in pairing with the four natural bases but selective for pairing with each other rather than with the natural bases. For example, compound 2 selectively pairs with itself rather than with A, T, G, or C; the magnitude of this selectivity is found to be 6.5-9.3 °C in Tm or 1.5-1.8 kcal/mol in free energy (25 °C). All possible hydrophobic pairing combinations of 1, 2, and 3 were examined. Results show that the pairing affinity depends on the nature of the pairs and on position in the duplex. The highest affinity pairs are found to be the 1-1 and 2-2 self-pairs and the 1-2 heteropair. The best stabilization occurs when the pairs are placed at the ends of duplexes rather than internally; the internal pairs may be destabilized by imperfect steric mimicry which leads to non-ideal duplex structure. In some cases the hydrophobic pairs are significantly stabilizing to the DNA duplex; for example, when situated at the end of a duplex, the 1-1 pair is more stabilizing than a T-A pair. When situated internally, the affinity of the 1-1 pair is the same as, or slightly better than, the analogous T-T mismatch pair, which is known to have two hydrogen bonds. The studies raise the possibility that hydrogen bonds may not always be required for the formation of stable duplex DNA-like structure. In addition, the results point out the importance of solvation and desolvation in natural base pairing, and lend new support to the idea that hydrogen bonds in DNA may be more important for specificity of pairing than for affinity. Finally, the study raises the possibility of using these or related base pairs to expand the genetic code beyond the natural A-T and G-C pairs.

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