138373-37-2Relevant academic research and scientific papers
Efficient synthesis of 2′-C-α-aminomethyl-2′- deoxynucleosides
Li, Nan-Sheng,Piccirilli, Joseph A.
supporting information; experimental part, p. 8754 - 8756 (2012/10/08)
Starting from methyl 3,5-di-O-benzyl-2-keto-α-d-ribofuranoside, a convergent, six-step synthesis is developed to give efficiently all four 2′-C-α-aminomethyl-2′-deoxynucleosides (U, C, A, G) in 38%, 42%, 12%, 12% yield, respectively. Convergence is achieved by the glycosylation of persilylated nucleobases with methyl 2-α-phthalimidomethyl ribofuranoside.
Nucleotides. LXXIV* synthesis of α-D-arabino-oligonucleotides
Henke, Christoph,Pfleiderer, Wolfgang
, p. 1665 - 1706 (2007/10/03)
□ The 5 α-D-arabinofuranosylnucleosides α-araU (15), α-araT (18), α-araC (22), α-araA (25), and α-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2′-hydroxy group at the sugar moiety were protected by the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) group (37-40) and the amide function in α-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5′-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3′-OH group led to the monomeric building blocks 66-75 as well as the 3′-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-α- arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between α-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-α-D-arabinonucleotide with a complementary oligo-2′-deoxy-β-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-α-arabino- nucleotide synthesis were furthermore demonstrated by the synthesis of the tα-ANAhis a structural analog of the natural tRNAhis of the phage T5. Copyright Taylor & Francis Group, LLC.
Synthesis and biological activity of a series of methylene-expanded oxetanocin nucleoside analogues
Jung, Michael E.,Toyota, Akemi,De Clercq, Erik,Balzarini, Jan
, p. 499 - 520 (2007/10/03)
A series of methylene-expanded oxetanocin nucleoside analogues, e.g. analogues of 2 and the known antiviral nucleosides AZT, FLT, and ddC (3) were prepared by a very direct route beginning with the readily available (S)-glycidol 4 and proceeding via the dihydrofuran-3-methanols 9a,b. Biological testing of these modified nucleosides indicates that they are non-cytotoxic compounds with generally weak antiviral activity. However, the guanosine analogue 2G showed pronounced activity vs. herpes simplex virus type 1 (HSV-1) in cell culture and was HSV-1-encoded thymidine kinase dependent. This compound is therefore an interesting new lead structure for the development of new anti-HSV agents.
An unusual solvent effect on the regiochemical outcome (N-9 versus N-7) of guanine glycosylation using Robins' reagent (2-N-acetyl-6-O- diphenylcarbamoylguanine)
Cheung, Adrian Wai-Hing,Sidduri, Achyutharao,Garofalo, Lisa M.,Goodnow Jr., Robert A.
, p. 3303 - 3307 (2007/10/03)
An unexpectedly low N-9/N-7 regioselectivity was obtained when Robins reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine) was coupled with a D- glucosamine derivative under trimethylsilyl trifluoromethanesulfonate activation. An unprecedented solvent effect (toluene versus dichloroethane) on the N-9/N-7 ratio was also observed in the same study. The use of 2-N- acetyl-6-O-benzylguanine to successfully overcome the above regioselectivity problem is described. (C) 2000 Elsevier Science Ltd.
