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Volumn 37, Issue 4, 2008, Pages 448-449

An unusual iodinated 5′-deoxyxylofuranosyl nucleoside from an Okinawan Ascidian, Diplosoma sp.

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Indexed keywords


EID: 43149085541     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2008.448     Document Type: Article
Times cited : (12)

References (28)
  • 2
    • 0036007872 scopus 로고    scopus 로고
    • and previous reports in this series
    • b) D. J. Faulkner, Nat. Prod. Rep. 2002, 19, 1, and previous reports in this series.
    • (2002) Nat. Prod. Rep , vol.19 , pp. 1
    • Faulkner, D.J.1
  • 5
    • 43149113289 scopus 로고    scopus 로고
    • Taxonomical assignment was performed by Prof. Euichi Hirose, University of the Ryukyus
    • Taxonomical assignment was performed by Prof. Euichi Hirose, University of the Ryukyus.
  • 6
    • 43149110236 scopus 로고    scopus 로고
    • To the best of our knowledge, there have been no reports on naturally occurring xylofuranosyl or 5′-deoxyxylofuranosyl nucleosides
    • To the best of our knowledge, there have been no reports on naturally occurring xylofuranosyl or 5′-deoxyxylofuranosyl nucleosides.
  • 19
    • 43149108199 scopus 로고    scopus 로고
    • +, 7), 303 (3), 289 (13), 261 (33), 260 (100), 233 (18).
    • +, 7), 303 (3), 289 (13), 261 (33), 260 (100), 233 (18).
  • 21
    • 43149084647 scopus 로고    scopus 로고
    • 2SO, 500 MHz] δ 1.17 (3H, s, Me), 1.23 (3H, d, J = 4.6 Hz, Me5′), 1.32 (3H, s, Me), 2.95 (3H, s, OMe), 3.88 (1H, dd, J = 3.4, 4.6 Hz, H3′), 4.12 (1H, qd, J = 3.4, 6.4 Hz, H4′), 4.22 (1H, brs, H2′), 5.83 (1H, d, J = 4.6Hz, OH3′), 6.04 (1H, d, J = 2.0 Hz, H1′), 7.63 (1H, s, H8), 8.11 (1H, s, H2).
    • 2SO, 500 MHz] δ 1.17 (3H, s, Me), 1.23 (3H, d, J = 4.6 Hz, Me5′), 1.32 (3H, s, Me), 2.95 (3H, s, OMe), 3.88 (1H, dd, J = 3.4, 4.6 Hz, H3′), 4.12 (1H, qd, J = 3.4, 6.4 Hz, H4′), 4.22 (1H, brs, H2′), 5.83 (1H, d, J = 4.6Hz, OH3′), 6.04 (1H, d, J = 2.0 Hz, H1′), 7.63 (1H, s, H8), 8.11 (1H, s, H2).
  • 24
    • 43149086433 scopus 로고    scopus 로고
    • 9: HR-ESIMS m/z 534.9340 (M, Na, calcd for C20H18Br2NaO6: 534.9368, 1HNMR (CDCl3, 400 MHz) δ 7.92 (d, J, 8.8 Hz, 2H, 7.88 (d, J, 8.8 Hz, 2H, 7.59 (d, J, 8.8 Hz, 2H, 7.58 (d, J, 8.8 Hz, 2H, 5.51 (d, J, 5.4 Hz, 1H, 5.44 (s, 1H, 5.01 (s, 1H, 4.69 (m, 1H, 3.46 (s, 3H, 1.32 (d, J, 6.8 Hz, 3H, 10: HR-ESIMS m/z 740.8857 (M, H, calcd for C25H 20Br2IN4O5: 740.8845, 1HNMR (CDCl3, 400 MHz) δ 8.21 (s, 1H, 7.90 (d, J, 8.3 Hz, 2H, 7.89 (d, J, 8.3 Hz, 2H, 7.66 (d, J, 8.3 Hz, 2H, 7.60 (d, J, 8.3 Hz, 2H, 7.43 (s, 1H, 6.51 (s, 1H, 5.74 (s, 1H, 5.64 (d, J, 3.4 Hz, 1H, 4.69 (m, 1H, 1.42 d, J, 6.4 Hz, 3H
    • 3, 400 MHz) δ 8.21 (s, 1H), 7.90 (d, J = 8.3 Hz, 2H), 7.89 (d, J = 8.3 Hz, 2H), 7.66 (d, J = 8.3 Hz, 2H), 7.60 (d, J = 8.3 Hz, 2H), 7.43 (s, 1H), 6.51 (s, 1H), 5.74 (s, 1H), 5.64 (d, J = 3.4 Hz, 1H), 4.69 (m, 1H), 1.42 (d, J = 6.4 Hz, 3H).
  • 27
    • 43149086660 scopus 로고    scopus 로고
    • Positive chirality between the p-bromobenzoyl chromophores of 10 also indicated that the sugar moiety in 1 was of the D-xylose series (2′R and 3′S configuration).
    • Positive chirality between the p-bromobenzoyl chromophores of 10 also indicated that the sugar moiety in 1 was of the D-xylose series (2′R and 3′S configuration).


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