Application of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite for in situ preparation of deoxyribonucleoside phosphoramidites and their use in polymer-supported synthesis of oligodeoxyribonucleotides - PubMed (original) (raw)
Application of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite for in situ preparation of deoxyribonucleoside phosphoramidites and their use in polymer-supported synthesis of oligodeoxyribonucleotides
J Nielsen et al. Nucleic Acids Res. 1986.
Free PMC article
Abstract
Deoxyribonucleoside phosphoramidites are prepared in situ from 5'-O,N-protected deoxyribonucleosides and 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite with tetrazole as catalyst, and the solutions applied directly on an automatic solid-phase DNA synthesizer. Using LCAA-CPG support and a cycle time of 12.5 min, oligonucleotides of 16-25 bases are obtained with a DMT-efficiency per cycle of 98.0-99.3%. The crude and fully deblocked products are of a purity comparable to that obtained using purified phosphoramidites. In case of d(G)16 the product was difficult to analyse and a better product was not obtained using doubly protected (O-6 diphenylcarbamoyl) guanine.
Similar articles
- In situ activation of bis-dialkylaminophosphines--a new method for synthesizing deoxyoligonucleotides on polymer supports.
Barone AD, Tang JY, Caruthers MH. Barone AD, et al. Nucleic Acids Res. 1984 May 25;12(10):4051-61. doi: 10.1093/nar/12.10.4051. Nucleic Acids Res. 1984. PMID: 6728676 Free PMC article. - Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides.
Pon RT, Damha MJ, Ogilvie KK. Pon RT, et al. Nucleic Acids Res. 1985 Sep 25;13(18):6447-65. doi: 10.1093/nar/13.18.6447. Nucleic Acids Res. 1985. PMID: 4059050 Free PMC article. - Frontiers and approaches to chemical synthesis of oligodeoxyribonucleotides.
Abramova T. Abramova T. Molecules. 2013 Jan 15;18(1):1063-75. doi: 10.3390/molecules18011063. Molecules. 2013. PMID: 23322070 Free PMC article. Review. - Preparation of trinucleotide phosphoramidites as synthons for the synthesis of gene libraries.
Suchsland R, Appel B, Müller S. Suchsland R, et al. Beilstein J Org Chem. 2018 Feb 13;14:397-406. doi: 10.3762/bjoc.14.28. eCollection 2018. Beilstein J Org Chem. 2018. PMID: 29520304 Free PMC article. Review.
Cited by
- Synthesis of Substituted Cy5 Phosphoramidite Derivatives and Their Incorporation into Oligonucleotides Using Automated DNA Synthesis.
Meares A, Susumu K, Mathur D, Lee SH, Mass OA, Lee J, Pensack RD, Yurke B, Knowlton WB, Melinger JS, Medintz IL. Meares A, et al. ACS Omega. 2022 Mar 22;7(13):11002-11016. doi: 10.1021/acsomega.1c06921. eCollection 2022 Apr 5. ACS Omega. 2022. PMID: 35415341 Free PMC article. - Solid-phase synthesis of DNA fragments containing the modified base 7-hydro-8-oxo-2'-deoxyguanosine.
Roelen HC, Saris CP, Brugghe HF, van den Elst H, Westra JG, van der Marel GA, van Boom JH. Roelen HC, et al. Nucleic Acids Res. 1991 Aug 25;19(16):4361-9. doi: 10.1093/nar/19.16.4361. Nucleic Acids Res. 1991. PMID: 1886763 Free PMC article. - Retracted Article: Divergent synthesis of 5-substituted pyrimidine 2'-deoxynucleosides and their incorporation into oligodeoxynucleotides for the survey of uracil DNA glycosylases.
Tran A, Zheng S, White DS, Curry AM, Cen Y. Tran A, et al. Chem Sci. 2020 Oct 7;11(43):11818-11826. doi: 10.1039/d0sc04161k. Chem Sci. 2020. PMID: 34123208 Free PMC article. Retracted. - Polymerase incorporation and miscoding properties of 5-chlorouracil.
Kim CH, Darwanto A, Theruvathu JA, Herring JL, Sowers LC. Kim CH, et al. Chem Res Toxicol. 2010 Apr 19;23(4):740-8. doi: 10.1021/tx900302j. Chem Res Toxicol. 2010. PMID: 20104909 Free PMC article.
References
- Nucleic Acids Res. 1983 May 11;11(9):2575-84 - PubMed
- Nucleic Acids Res. 1984 May 25;12(10):4051-61 - PubMed
- Nucleic Acids Res. 1984 Jun 11;12(11):4539-57 - PubMed
- Annu Rev Biochem. 1984;53:323-56 - PubMed
- Nucleic Acids Symp Ser. 1985;(16):257-60 - PubMed
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources