On the determination of the stereochemistry of semisynthetic natural product analogues using chiroptical spectroscopy: Desulfurization of epidithiodioxopiperazine fungal metabolites

Chemistry - A European Journal

Volumn 17, Issue 42, 2011, Pages 11868-11875

  Cherblanc, Fanny ^a   Lo, Ya Pei ^a   De Gussem, Ewoud ^a,b,c   Alcazar Fuoli, Laura ^a   Bignell, Elaine ^a   He, Yanan ^d   Chapman Rothe, Nadine ^e   Bultinck, Patrick ^a,c   Herrebout, Wouter A ^a,b   Brown, Robert ^e   Rzepa, Henry S ^a   Fuchter, Matthew J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF ANTWERP   (Belgium)

^c GHENT UNIVERSITY   (Belgium)

^d BIOTOOLS INC   (United States)

^e HAMMERSMITH HOSPITAL   (United Kingdom)

Author keywords

circular dichroism; configuration determination; desulfurization; natural products; vibrational spectroscopy

Indexed keywords

CHIROPTICAL SPECTROSCOPY; CONFIGURATION DETERMINATION; ELECTRONIC CIRCULAR DICHROISM; FUNGAL METABOLITES; NATURAL PRODUCTS; PLAUSIBLE MECHANISMS; VIBRATIONAL CIRCULAR DICHROISM SPECTRUM;

DESULFURIZATION; METABOLISM; METABOLITES; OPTICAL ROTATION; STEREOCHEMISTRY; VIBRATIONAL SPECTROSCOPY;

DICHROISM;

BIOLOGICAL PRODUCT; PIPERAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; FUNGUS; INFRARED SPECTROPHOTOMETRY; METABOLISM; SPECTROSCOPY; STEREOISOMERISM;

BIOLOGICAL AGENTS; CIRCULAR DICHROISM; FUNGI; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PIPERAZINES; SPECTROPHOTOMETRY, INFRARED; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 80053481022     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101129     Document Type: Article

References (45)

1. K. C. Nicolaou, S. A. Snyder, Angew. Chem. 2005, 117, 1036-1069
2. Angew. Chem. Int. Ed. 2005, 44, 1012-1044.
3. B. M. Trost, P. E. Harrington, J. Am. Chem. Soc. 2004, 126, 5028-5029
4. Y. Morimoto, T. Iwai, T. Kinoshita, J. Am. Chem. Soc. 2000, 122, 7124-7125
5. T. G. Minehan, L. Cook-Blumberg, Y. Kishi, M. R. Prinsep, R. E. Moore, Angew. Chem. 1999, 111, 975-977
6. Angew. Chem. Int. Ed. 1999, 38, 926-928
7. T. M. Kamenecka, S. J. Danishefsky, Angew. Chem. 1998, 110, 3166-3168
8. Angew. Chem. Int. Ed. 1998, 37, 2995-2998
9. P. Wipf, Y. Uto, J. Org. Chem. 2000, 65, 1037-1049
10. F. Yokokawa, H. Fujiwara, T. Shioiri, Tetrahedron 2000, 56, 1759-1775.
11. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley -Blackwell, New York, 1994.
12. L. D. Barron, A. D. Buckingham, Chem. Phys. Lett. 2010, 492, 199-213.
13. W. Kuhn, Z. Phys. Chem. Abt. B 1935, 31, 23-57
14. J. G. Kirkwood, J. Chem. Phys. 1937, 5, 479-491
15. W. J. Kauznman, J. E. Walter, H. Eyring, Chem. Rev. 1940, 26, 339-407.
16. M. G. J. Baud, T. Leiser, F.-J. Meyer-Almes, M. J. Fuchter, Org. Biomol. Chem. 2011, 9, 659-662.
17. D. Greiner, T. Bonaldi, R. Eskeland, E. Roemer, A. Imhof, Nat. Chem. Biol. 2005, 1, 143-145.
18. D. M. Gardiner, P. Waring, B. Howlett, Microbiol. 2005, 151, 1021-1032.
19. S. Udagawa, T. Muroi, H. Kurata, S. Sekita, K. Yoshihira, S. Natori, M. Umeda, Can. J. Microbiol. 1979, 25, 170-177
20. S. Sekita, K. Yoshihira, S. Natori, S. Udagawa, T. Muroi, S. Sugiyama, H. Kurata, M. Umeda, Can. J. Microbiol. 1981, 27, 766-772
21. T. Saito, Y. Suzuki, K. Koyama, S. Natori, Y. Iitaka, T. Kinoshita, Chem. Pharm. Bull. 1988, 36, 1942-1956.
22. K. M. Cook, S. T. Hilton, J. Mecinovic, W. B. Motherwell, W. D. Figg, C. J. Schofield, J. Biol. Chem. 2009, 284, 26831-26838.
23. C. R. Isham, J. D. Tibodeau, W. Jin, R. Xu, M. M. Timm, K. C. Bible, Blood 2007, 109, 2579-2588.
24. S. Safe, A. Taylor, J. Chem. Soc. C 1971, 1189-1192
25. J. D. M. Herscheid, M. W. Tijhuis, J. H. Noordik, H. C. J. Ottenheijm, J. Am. Chem. Soc. 1979, 101, 1159-1162
26. J. P. Ferezou, A. Quesneauthierry, M. Cesario, C. Pascard, M. Barbier, J. Am. Chem. Soc. 1983, 105, 5402-5406.
27. P. G. Sammes, Prog. Chem. Org. Nat. Prod. 1975, 32, 51-118.
28. T. Sato, T. Hino, Tetrahedron 1976, 32, 507-513.
29. C. L. L. Chai, J. A. Elix, P. B. Huleatt, P. Waring, Bioorg. Med. Chem. 2004, 12, 5991-5995.
30. Gaussian 09, Revision B1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
31. J. D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 2008, 10, 6615-6620.
32. P. Rivera-Fuentes J. L. Alonso-Gomez, A. G. Petrovic, P. Seiler, F. Santoro, N. Harada, N. Berova, H. S. Rzepa, F. Diederich, Chem. Eur. J. 2010, 16, 9796-9807.
33. L. A. Nafie, Nat. Prod. Commun. 2008, 3, 451-466.
34. I. M. Alecu, J. J. Zheng, Y. Zhao, D. G. Truhlar, J. Chem. Theory Comput. 2010, 6, 2872-2887.
35. V. P. Nicu, E. Debie, W. Herrebout, B. Van der Veken, P. Bultinck, E. J. Baerends, Chirality 2009, 21, E 287 -E 297
36. E. Debie, P. Bultinck, W. Herrebout, B. van der Veken, Phys. Chem. Chem. Phys. 2008, 10, 3498-3508.
37. T. Kuppens, K. Vandyck, J. Van der Eycken, W. Herrebout, B. van der Veken, P. Bultinck, Spectrochim. Acta, Part A 2007, 67, 402-411
38. T. Kuppens, W. Langenaeker, J. P. Tollenaere, P. Bultinck, J. Phys. Chem. A 2003, 107, 542-553
39. T. Kuppens, K. Vandyck, J. Van der Eycken, W. Herrebout, B. J. van der Veken, P. Bultinck, J. Org. Chem. 2005, 70, 9103-9114
40. E. Debie, E. De Gussem, R. K. Dukor, W. Herrebout, L. A. Nafie, P. Bultinck, ChemPhysChem 2011, 12, 1542- 1549.
41. E. Debie, P. Bultinck, L. A. Nafie, R. K. Dukor, CompareVOA, 2010, BioTools, Jupiter, Florida (USA).
42. A. J. Parker, N. Kharasch, Chem. Rev. 1959, 59, 583-628.
43. D. N. Harpp, J. G. Gleason, J. Am. Chem. Soc. 1971, 93, 2437-2445.
44. K. C. Murdock, J. Med. Chem. 1974, 17, 827-835.
45. G. Pontecorvo, J. A. Roper, L. M. Hemmons, K. D. Macdonald, A. W. Bufton, Adv. Genet. 1953, 5, 141-238.