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Volumn 33, Issue 15-16, 1994, Pages 1654-1657

Synthesis of an Azathymidine and Its Incorporation into Oligonucleotides

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EID: 0027966522     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199416541     Document Type: Article
Times cited : (43)

References (31)
  • 8
    • 84989540396 scopus 로고    scopus 로고
    • Compounds of type 1 with R = OH are also known [5], but no corresponding oligonucleotides have been reported.
  • 17
    • 84989503422 scopus 로고    scopus 로고
    • 6 was purified by flash chromatography and then recrystallized from acetone. In contrast to what might be implied from the above literature report, optically active material had to be recovered from the mother liquor of the recrystallization mixture, while the crystalline precipitate consisted mainly of the racemate. The [α] D25 value of 6 was −65.5 (c = 1.01 in MeOH), m.p. 99–100°C (ref. + )−6: [α] D20 = +59 (c = 1.0 in MeOH), m.p. 100–101°C, and its ee was determined as 96% by chiral HPLC.
  • 24
    • 84989512235 scopus 로고    scopus 로고
    • +).
  • 27
    • 84989581789 scopus 로고    scopus 로고
    • Coupling times of 10 min were routinely employed for the incorporation of 21.
  • 28
    • 84989569732 scopus 로고    scopus 로고
    • Compound 4 is completely stable under the conditions of oligonucleotide synthesis. In addition, incorporation of 4 as an intact unit into the various oligonucleotides was ascertained by matrix‐assisted laser desorption time‐of‐flight (MALDI‐TOF) mass spectrometry [21].
  • 31
    • 84989569729 scopus 로고    scopus 로고
    • The natural nucleotide building block at the 3′‐end of the oligonucleotide is present only for synthetic convenience, as it allows solid‐phase oligonucleotide synthesis to be conducted starting from a commercially available support. This residue is removed from the oligonucleotide by the action of 3′‐exonucleases rather rapidly, independent of the nature of the adjacent building blocks. The degree of protection against degradation by 3′‐exonucleases conferred by the modified building blocks 4 in TCC AGG TGT CCG ttt C is therefore determined by the half‐life of the (n – 1) species generated by removal of the 3′‐terminal cytidine residue.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.