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Volumn 4, Issue 3, 2000, Pages 214-224

The dimethoxytrityl resin product anchored sequential synthesis method (DMT PASS): A conceptually novel approach to oligonucleotide synthesis

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EID: 0034395476     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op990095t     Document Type: Article
Times cited : (10)

References (36)
  • 3
    • 85037780439 scopus 로고    scopus 로고
    • note
    • The following abbreviations are used throughout this account: ACN, acetonitrile; AcCl, acetyl chloride; Abz, 4-acetoxybenzyl; TBS, tertbutyldimethylsilyl; TBDPS, tert-butyldiphenylsilyl; DCA, dichloroacetic acid; DCM, dichloromethane; DCI, 4,5-dicyanoimidazole; DMT PASS, dimethoxytrityl resin product anchored sequential synthesis; DMF, dimethylformamide; DIPA, diisopropylamine; DIPEA, diisopropylethylamine; EtOAc, ethyl acetate; HPLC, high-pressure liquid chromatography; LC/ MS, liquid chromatography/mass spectrometric; MMT, monomethoxytrityl; NPE, 4-nitrophenethyl; TBAP, tetrabutylammonium periodate; v/v volume/volume.
  • 6
    • 85037776718 scopus 로고    scopus 로고
    • note
    • Bz).
  • 7
    • 33847797467 scopus 로고
    • The polystyrene support employed in these studies was prepared according to the protocol of Farrall and Fréchet
    • The polystyrene support employed in these studies was prepared according to the protocol of Farrall and Fréchet (Farrall, M. J.; Fréchet, J. M. J. J. Org. Chem. 1976, 41, 3877-3882).
    • (1976) J. Org. Chem. , vol.41 , pp. 3877-3882
    • Farrall, M.J.1    Fréchet, J.M.J.2
  • 8
    • 85037763532 scopus 로고    scopus 로고
    • note
    • Typically, considerably larger excesses (up to 15 equiv vs 1-2 equiv) of MMT resin-bound amidites were required to accomplish full conversion of fully protected oligonucleotide substrates.
  • 16
    • 0038869742 scopus 로고
    • Schirmeister, H.; Pfleiderer, W. Helv. Chim. Acta 1994, 77, 11. For a review on the use of the 4-nitrophenethyl protecting group in oligonucleotide chemistry, see: Pfleiderer, W.; Himmelsbach, F.; Charubala, R.; Schirmeister, H.; Beiter, A.; Schulz, B.; Trichtinger, T. Nucleosides Nucleotides 1985, 4, 81.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 11
    • Schirmeister, H.1    Pfleiderer, W.2
  • 31
    • 0001523773 scopus 로고
    • Some aspects of H-phosphonate chemistry
    • Engel, R., Ed.; Marcel Dekker: New York
    • Stawinski, J. Some Aspects of H-Phosphonate Chemistry. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992; p 337-434.
    • (1992) Handbook of Organophosphorus Chemistry , pp. 337-434
    • Stawinski, J.1
  • 32
    • 85037770554 scopus 로고    scopus 로고
    • note
    • In fact, a tetrameric H-phosphonate substrate was prepared by successive application of the phenyl H-phosphonate resin DMT PASS method, and this compound did show a tendency to "oil out" in the extractive purification step.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.