View Item 

Show simple item record

The 4â Methylthioâ 1â Butyl Group for Phosphate/Thiophosphate Protection in Oligodeoxyribonucleotide Synthesis
dc.contributor.authorCieślak, Jacek
dc.contributor.authorGrajkowski, Andrzej
dc.contributor.authorLivengood, Victor
dc.contributor.authorBeaucage, Serge L.
dc.date.accessioned2018-05-15T20:12:41Z
dc.date.available2018-05-15T20:12:41Z
dc.date.issued2004-12
dc.identifier.citationCieślak, Jacek ; Grajkowski, Andrzej; Livengood, Victor; Beaucage, Serge L. (2004). "The 4â Methylthioâ 1â Butyl Group for Phosphate/Thiophosphate Protection in Oligodeoxyribonucleotide Synthesis." Current Protocols in Nucleic Acid Chemistry 19(1): 3.11.1-3.11.14.
dc.identifier.issn1934-9270
dc.identifier.issn1934-9289
dc.identifier.urihttps://hdl.handle.net/2027.42/143609
dc.description.abstractThe detailed preparation of deoxyribonucleoside phosphoramidites functionalized with a 4â methylthioâ 1â butyl group for P(III) protection is described, along with the incorporation of these phosphoramidites into DNA oligonucleotides via solidâ phase techniques. The versatility of the thermolabile 4â methylthioâ 1â butyl phosphate/thiophosphateâ protecting group is exemplified through its facile removal from oligonucleotides under neutral conditions or under standard basic conditions. The sulfonium salt that is produced during the thermolytic deprotection of oligonucleotides did not alter DNA nucleobases or desulfurize phosphorothioate diesters to a significant extent.
dc.publisherWiley Periodicals, Inc.
dc.subject.otherintramolecular cyclodeesterification
dc.subject.otherDeoxyribonucleoside phosphoramidites
dc.subject.other4â methylthioâ 1â butanol
dc.subject.otherphosphorus trichloride
dc.subject.otherbis(N,Nâ diisopropylamino)chlorophosphine
dc.subject.otherOâ (4â methylthioâ 1â butyl)â N,N,Nâ ²,Nâ ²â tetraisopropylphosphorodiamidite
dc.subject.otherthermolytic deprotection
dc.subject.otherSâ methyltetrahydrothiophenium chloride
dc.titleThe 4â Methylthioâ 1â Butyl Group for Phosphate/Thiophosphate Protection in Oligodeoxyribonucleotide Synthesis
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelPublic Health
dc.subject.hlbsecondlevelBiological Chemistry
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelHealth Sciences
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/143609/1/cpnc0311.pdf
dc.identifier.doi10.1002/0471142700.nc0311s19
dc.identifier.sourceCurrent Protocols in Nucleic Acid Chemistry
dc.identifier.citedreferenceChmielewski, M.K., Marchán, V., CieÅ lak, J., Grajkowski, A., Livengood, V., Münch, U., Wilk, A., and Beaucage, S.L. 2003. Thermolytic carbonates for potential 5â ²â hydroxyl protection of deoxyribonucleosides. J. Org. Chem. 68: 10003 â 10012.
dc.identifier.citedreferenceCieÅ lak, J. and Beaucage, S.L. 2003. Thermolytic properties of 3â (2â pyridyl)â 1â propyl and 2â [ N â methylâ N â (2â pyridyl)]aminoethyl phosphate/thiophosphate protecting groups in solidâ phase synthesis of oligodeoxyribonucleotides. J. Org. Chem. 68: 10123 â 10129.
dc.identifier.citedreferenceCieÅ lak, J., Grajkowski, A., Livengood, V., and Beaucage, S.L. 2004. Thermolytic 4â methylthioâ 1â butyl group for phosphate/thiophosphate protection in solidâ phase synthesis of DNA oligonucleotides. J. Org. Chem. 69: 2509 â 2515.
dc.identifier.citedreferenceGrajkowski, A., Wilk, A., Chmielewski, M.K., Phillips, L.R., and Beaucage, S.L. 2001. The 2â ( N â formyl, N â methyl)aminoethyl group as a potential phosphate/thiophosphate protecting group in solidâ phase oligodeoxyribonucleotide synthesis. Org. Lett. 3: 1287 â 1290.
dc.identifier.citedreferenceGrajkowski, A., CieÅ lak, J., Chmielewski, M.K., Marchán, V., Phillips, L.R., Wilk, A., and Beaucage, S.L. 2003. Conceptual â heatâ drivenâ approach to the synthesis of DNA oligonucleotides on microarrays. Ann. N.Y. Acad. Sci. 1002: 1 â 11.
dc.identifier.citedreferenceGuo, Q.M. 2003. DNA microarray and cancer. Curr. Opin. Oncol. 15: 36 â 43.
dc.identifier.citedreferenceIyer, R.P., Phillips, L.R., Egan, W., Regan, J.B., and Beaucage, S.L. 1990. The automated synthesis of sulfurâ containing oligodeoxyribonucleotides using 3 H â 1,2â benzodithiolâ 3â oneâ 1,1â dioxide as a sulfurâ transfer reagent. J. Org. Chem. 55: 4693 â 4699.
dc.identifier.citedreferenceRhodes, D.R. and Chinnaiyan, A.M. 2002. DNA microarrays: Implications for clinical medicine. J. Invest. Surg. 15: 275 â 279.
dc.identifier.citedreferenceWilk, A., Chmielewski, M.K., Grajkowski, A., Phillips, L.R., and Beaucage, S.L. 2002. The 3â [( N â tert â butyl)carboxamido]â 1â propyl group as an attractive phosphate/thiophosphate protecting group for solidâ phase oligodeoxyribonucleotide synthesis. J. Org. Chem. 67: 6430 â 6438.
dc.identifier.citedreferenceWilk, A., Chmielewski, M.K., Grajkowski, A., Phillips, L.R., and Beaucage, S.L. 2001. The 4â oxopentyl group as a labile phosphate/thiophosphate protecting group for synthetic oligodeoxyribonucleotides. Tetrahedron Lett. 42: 5635 â 5639.
dc.identifier.citedreferenceWilk, A., Grajkowski, A., Srinivasachar, K., and Beaucage, S.L. 1999b. Improved chemistry for the production of synthetic oligodeoxyribonucleotides. Antisense Nucleic Acid Drug Dev. 9: 361 â 366.
dc.identifier.citedreferenceWilk, A., Grajkowski, A., Phillips, L.R., and Beaucage, S.L. 1999a. The 4â [ N â methylâ N â (2,2,2â trifluoroacetyl)amino]butyl group as an alternative to the 2â cyanoethyl group for phosphate protection in the synthesis of oligodeoxyribonucleotides. J. Org. Chem. 64: 7515 â 7522.
dc.identifier.citedreferenceSinha, N.D., Biernat, J., McManus, J., and Köster, H. 1984. Polymer support oligonucleotide synthesis. 18. Use of βâ cyanoethylâ N, N,â dialkylamino/â N â morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucl. Acids Res. 12: 4539 â 4557.
dc.identifier.citedreferenceBarone, A.D., Tang, J.â T., and Caruthers, M.H. 1984. In situ activation of bisâ dialkylaminophosphinesâ A new method for synthesizing deoxyoligonucleotides on polymer supports. Nucl. Acids Res. 12: 4051 â 4061.
dc.identifier.citedreferenceBoal, J.H., Wilk, A., Harindranath, N., Max, E.E., Kempe, T., and Beaucage, S.L. 1996. Cleavage of oligodeoxyribonucleotides from controlledâ pore glass supports and their rapid deprotection by gaseous amines. Nucl. Acids Res. 24: 3115 â 3117.
dc.identifier.citedreferenceByrne, B. and Lafleur Lawter, L.M. 1986. The preparation of trimethylsulfonium chloride from methyl chloroformate and dimethyl sulfide. Tetrahedron Lett. 27: 1233 â 1236.
dc.owningcollnameInterdisciplinary and Peer-Reviewed


Files in this item

Name:
cpnc0311.pdf
Size:
158.9KB
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.