Revised structure of tolyporphin A

Angewandte Chemie - International Edition

Volumn 38, Issue 7, 1999, Pages 926-928

  Minehan, Thomas G ^a   Cook Blumberg, Laura ^a   Kishi, Yoshito ^a   Prinsep, Michèle R ^b   Moore, Richard E ^c  

^a HARVARD UNIVERSITY   (United States)

^b UNIVERSITY OF WAIKATO   (New Zealand)

^c UNIVERSITY OF HAWAII   (United States)

Author keywords

DNA structures; Nucleosides; Nucleotides; Watson Crick base pairs

Indexed keywords

ACETOACETIC ACID; PORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CONFORMATION; DIASTEREOISOMER; IRRADIATION; SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033118502     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19990401)38:7<926::aid-anie926>3.0.co;2-w     Document Type: Article

References (24)

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12. 2] retained B-form without losing any one of 22 Watson-Crick type hydrogen bonds. However, slight deformations were noted for the base pairs and ribose-backbones adjacent to the base pair B.
13. F. Seela, W. Bourgeois, Synthesis 1989, 912.
14. C. C. Bhat in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (Eds.: W. W. Zorbach, R. S. Tipson), Wiley, 1968, p. 521.
15. For the numberings adopted in this paper, see structures 3, 8a, and 9a. "R." and "L." refer to the right- and left-side rings, respectively.
16. M. M. Alauddin, P. S. Conti, Tetrahedron 1994, 50, 1699.
17. For a review on Mitsunobu reactions, see: O. Mitsunobu, Synthesis 1981, 1.
18. 3/DMSO/RT) with 1-ethylthymine.
19. The L.1-Me base pairs corresponding to 8b and 91) were also subjected to X-ray structure analyses; their structural characteristics were found to be very similar to those observed for 8b and 9b, respectively. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publica-tion no. CCDC-114659 (8b) and CCDC-114660 (9b). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
20. For example, see: Nucleic Acids in Chemistry and Biology, 2nd ed. (Eds.: G. M. Blackburn, M. J. Gait), Oxford University Press, Oxford, 1996, p. 21.
21. For reviews on dynamic NMR spectroscopy, see: E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 502, and references therein.
22. 2/ RT. AOC = allyloxycarbonyl, BT=benzotriazole.
23. 3/DMSO/RT) with mesylated 5.
24. Note added in proof (February 11, 1999): In the sense of primary hydrogen-bonding base pairing, only Watson-Crick and reversed Watson-Crick base pairings are possible for models A and B. However, it should be noted that Hoogsteen triplets such as T-AT and T-GC are envisioned for model B, but not for model A.