View Item 

Show simple item record

Synthesis of Protected 2′‐Deoxy‐2′‐fluoro‐β‐D‐arabinonucleosides
dc.contributor.authorElzagheid, Mohamed I.
dc.contributor.authorViazovkina, Ekaterina
dc.contributor.authorDamha, Masad J.
dc.date.accessioned2020-01-13T15:09:29Z
dc.date.available2020-01-13T15:09:29Z
dc.date.issued2002-09
dc.identifier.citationElzagheid, Mohamed I.; Viazovkina, Ekaterina; Damha, Masad J. (2002). "Synthesis of Protected 2′‐Deoxy‐2′‐fluoro‐β‐D‐arabinonucleosides." Current Protocols in Nucleic Acid Chemistry 10(1): 1.7.1-1.7.19.
dc.identifier.issn1934-9270
dc.identifier.issn1934-9289
dc.identifier.urihttps://hdl.handle.net/2027.42/152767
dc.description.abstractThis unit describes in detail the preparation of protected 2’‐deoxy‐2’‐fluoroarabinonucleosides. These building blocks are required for the synthesis of 2’‐deoxy‐2’‐fluoroarabinonucleic acid (2’F‐ANA), an oligonucleotide analog exhibiting very promising antisense properties. The preparation of phosphoramidites from these building blocks and the synthesis of 2’F‐ANA are described elsewhere in the manual.
dc.publisherWiley Periodicals, Inc.
dc.publisherInternational Society for Nucleosides, Nucleotides, and Nucleic Acids
dc.titleSynthesis of Protected 2′‐Deoxy‐2′‐fluoro‐β‐D‐arabinonucleosides
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelBiological Chemistry
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelPublic Health
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelHealth Sciences
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/152767/1/cpnc0107.pdf
dc.identifier.doi10.1002/0471142700.nc0107s10
dc.identifier.sourceCurrent Protocols in Nucleic Acid Chemistry
dc.identifier.citedreferenceTann, C.H., Brodfuehrer, P.R., Brundidge, S.P., Sapino, C. Jr., and Howell, H.G. 1985. Fluorocarbohydrate in synthesis. An efficient synthesis of 1‐(2‐deoxy‐2‐fluoro‐β‐ D ‐arabinofuranosyl)‐5‐iodouracil (β‐FIAU) and 1‐(2‐deoxy‐2‐fluoro‐β‐ D ‐arabinofuranosyl)thymine (β‐FMAU). J. Org. Chem. 50: 3644 ‐ 3647.
dc.identifier.citedreferenceDamha, M.J., Wilds, C.J., Novonha, A., Brunker, I., Borkow, G., Arion, D., and Parniak, M.A. 1998. Hybrids of RNA and arabinonucleic acids (ANA and 2′F‐ANA) are substrates of ribonuclease H. J. Am. Chem. Soc. 120: 12976 ‐ 12977.
dc.identifier.citedreferenceEberhardt, E.S., Panasik, N. Jr., and Raines, R.T. 1996. Inductive effects on the energetics of prolyl peptide bond isomerization: Implications for collagen folding and stability. J. Am. Chem. Soc. 118: 12261 ‐ 12266.
dc.identifier.citedreferenceHerdewijn, P., VanAerschot, A., and Kerremans, L. 1989. Synthesis of nucleosides fluorinated in the sugar moiety. The application of diethylaminosulfur trifluoride to the synthesis of fluorinated nucleosides. Nucleosides Nucleotides 8: 65 ‐ 96.
dc.identifier.citedreferenceHolmgren, S.K., Bretscher, L.E., Taylor, K.M., and Raines, R.T. 1999. A hyperstable collagen mimic. Chem. Biol. 6: 63 ‐ 70.
dc.identifier.citedreferenceHowell, H.G., Brodfuehrer, P.R., Brundidge, S.P., Benigni, D.A., and Sapino, C. Jr. 1988. Antiviral nucleosides. A stereospecific, total synthesis of 2′‐fluoro‐2′‐deoxy‐β‐ D ‐arabinofuranosyl nucleosides. J. Org. Chem. 53: 85 ‐ 88.
dc.identifier.citedreferenceKierzek, R. 1985. The synthesis of 5′‐ O ‐dimethoxytrityl‐ N ‐acetyl‐2′‐deoxynucleosides. Improved “transient protection” approach. Nucleosides Nucleotides 4: 641 ‐ 649.
dc.identifier.citedreferenceMa, T., Lin, J.‐S., Newton, M.G., Cheng, Y.‐C., and Chu, C.K. 1997. Synthesis and anti hepatitis B virus activity of 9‐(2‐deoxy‐2‐fluoro‐β‐ L ‐arabinofuranosyl)purine nucleosides. J. Med. Chem. 40: 2750 ‐ 2754.
dc.identifier.citedreferenceMaruyama, T., Takamatsu, S., Kozai, S., Satoh, Y., and Izawa, K. 1999. Synthesis of 9‐(2‐deoxy‐2‐fluoro‐β‐ D ‐arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull. 47: 966 ‐ 970.
dc.identifier.citedreferenceMiddleton, W.J. 1975. New fluorinating reagents. Dialkylaminosulfur fluorides. J. Org. Chem. 40: 574 ‐ 578.
dc.identifier.citedreferenceLok, C.‐N., Viazovkina, E., Min, K.‐L., Nagy, E., Wilds, C.J., Damha, M.J., and Parniak, M.A. 2002. Potent gene‐specific inhibitory properties of mixed‐backbone antisense oligonucleotides comprised of 2′‐deoxy‐2′‐fluoro‐ D ‐arabinose and 2′‐deoxyribose nucleotides. Biochemistry. 41: 3457 ‐ 3467.
dc.identifier.citedreferencePankiewicz, K.W. 2000. Fluorinated nucleosides. Carbohydr. Res. 327: 87 ‐ 105.
dc.identifier.citedreferencePankiewicz, K.W., Krzeminski, J., Cizewski, L.A., Ren, W.‐Y., and Watanabe, K.A. 1992. Synthesis of 9‐(2‐deoxy‐2‐fluoro‐β‐ D ‐arabinofuranosyl)adenine and hypoxanthine. An effect of C3′‐endo to C2′‐endo conformational shift on the reaction course of 2′‐hydroxyl group with DAST. J. Org. Chem. 57: 553 ‐ 559.
dc.identifier.citedreferenceScharer, O.D. and Verdine, G.L. 1995. A designed inhibitor of base‐excision DNA repair. J. Am. Chem. Soc. 117: 10781 ‐ 10782.
dc.identifier.citedreferenceStill, W.C., Kahn, M., and Mitra, A. 1978. Rapid chromatographic technique for preparative separation with moderate resolution. J. Org. Chem. 43: 2923 ‐ 2925.
dc.identifier.citedreferenceTennila, T., Azhayev, E., Vepsalainen, J., Laatikainen, R., Azhayev, A., and Mikhailopulo, I.A. 2000. Oligonucleotides containing 9‐(2‐deoxy‐2‐fluoro‐β‐ D ‐arabinofuranosyl)‐adenine and guanine: Synthesis, hybridization and antisense properties. Nucleosides Nucleotides Nucleic Acids. 19: 1861 ‐ 1884.
dc.identifier.citedreferenceWilds, C.J. and Damha, M.J. 2000. 2′‐Deoxy‐2′‐fluoro‐β‐ D ‐arabinonucleosides and oligonucleotides (2′F‐ANA): Synthesis and physicochemical studies. Nucl. Acids Res. 28: 3625 ‐ 3635.
dc.identifier.citedreferenceWatanabe, K.A., Chu, C.K., and Fox, J.J. June, 1988. 2‐Fluoro‐arabinofuranosyl purine nucleosides. U.S. patent 47,551,221.
dc.identifier.citedreferenceWower, J., Hixson, S.S., Sylvers, L.A., Xing, Y., and Zimmermann, R.A. 1994. Synthesis of 2,6‐diazido‐9‐(β‐ D ‐ribofuranosyl)purine 3′,5′‐bisphosphate: Incorporation into transfer RNA and photochemical labelling of Escherichia coli ribosomes. Bioconjug. Chem. 5: 158 ‐ 161.
dc.identifier.citedreferenceHerdewijn et al., 1989.See above.
dc.identifier.citedreferenceHowell et al., 1988.See above.
dc.identifier.citedreferencePankiewicz, 2000.See above.
dc.identifier.citedreferenceTann et al., 1985.See above.
dc.identifier.citedreferenceWilds and Damha, 2000.See above.
dc.identifier.citedreferenceBurchenal, J.H., Leyland‐Jones, B., Watanabe, B., Klein, R., Lopez, C., and Fox, J.J. 1983. Experimental and clinical studies on 2′‐fluoroarabinosyl pyrimidines and purine‐like C‐nucleosides. In Nucleosides, Nucleotides, and Their Biological Applications, Proceedings 5th International Round Table, pp. 47 ‐ 65. International Society for Nucleosides, Nucleotides, and Nucleic Acids, Montpellier, France.
dc.identifier.citedreferenceChu, C.K., Matulic‐Adamic, J., Huang, J.‐T., Chou, T.‐C., Burchenal, J.H., Fox, J.J., and Watanabe, K.A. 1989. Synthesis of some 9‐(2‐deoxy‐2‐fluoro‐β‐ D ‐arabinofuranosyl)‐9H‐purines and their biological activities. Chem. Pharm. Bull. 37: 336 ‐ 339.
dc.owningcollnameInterdisciplinary and Peer-Reviewed


Files in this item

Name:
cpnc0107.pdf
Size:
296.8KB
Format:
PDF
View/Open

Show simple item record

Remediation of Harmful Language

The University of Michigan Library aims to describe library materials in a way that respects the people and communities who create, use, and are represented in our collections. Report harmful or offensive language in catalog records, finding aids, or elsewhere in our collections anonymously through our metadata feedback form. More information at Remediation of Harmful Language.

Accessibility

If you are unable to use this file in its current format, please select the Contact Us link and we can modify it to make it more accessible to you.