Mollenynes B-E from the Marine Sponge Spirastrella mollis. Band-Selective Heteronuclear Single Quantum Coherence for Discrimination of Bromo-Chloro Regioisomerism in Natural Products

Journal of the American Chemical Society

Volumn 137, Issue 38, 2015, Pages 12343-12351

  Wang, Xiao ^a   Duggan, Brendan M ^b   Molinski, Tadeusz F ^a,b  

^a Department of Chemistry and Biochemistry ^*  (United States)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

BAND-SELECTIVE; HETERONUCLEAR SINGLE-QUANTUM COHERENCES; HIGH RESOLUTION; INTEGRATED ANALYSIS; ISOTOPE SHIFTS; MARINE SPONGE; NATURAL PRODUCTS; REGIOISOMERISM;

QUANTUM THEORY;

MOLLENYNE B; MOLLENYNE C; MOLLENYNE D; MOLLENYNE E; NATURAL PRODUCT; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT; CHLOROHYDRIN DERIVATIVE;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; HETERONUCLEAR SINGLE QUANTUM COHERENCE; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; SPIRASTRELLA MOLLIS; SPONGE (PORIFERA); STEREOISOMERISM; ANIMAL; CHEMISTRY; CONFORMATION; ISOLATION AND PURIFICATION; QUANTUM THEORY;

ANIMALS; BIOLOGICAL PRODUCTS; CHLOROHYDRINS; MOLECULAR CONFORMATION; PORIFERA; QUANTUM THEORY; STEREOISOMERISM;

EID: 84942925409     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b07858     Document Type: Article

References (60)

1. Gribble, G. W. Acc. Chem. Res. 1998, 31, 141-152 10.1021/ar9701777
2. Hartung, J. Angew. Chem., Int. Ed. 1999, 38 (9) 1209-1211 10.1002/(SICI)1521-3773(19990503)38:9<1209::AID-ANIE1209>3.0.CO;2-F
3. Gribble, G. W. J. Chem. Educ. 2004, 81, 1441-1449 10.1021/ed081p1441
4. Gribble, G. W. Mar. Drugs 2015, 13, 4044-4136 10.3390/md13074044
5. The originally proposed structure of 1 was incorrectly assigned with interchanged Br and Cl substituents but later corrected by an X-ray crystal structure: Mynderse, J. S.; Faulkner, D. J. J. Am. Chem. Soc. 1974, 96, 6771 10.1021/ja00828a045
6. van Engen, D.; Clardy, J.; Kho-Wiseman, E.; Crews, P.; Higgs, M. D.; Faulkner, D. J. Tetrahedron Lett. 1978, 19, 29-32 10.1016/S0040-4039(01)88974-7
7. Mynderse, J. S.; Faulkner, D. J. Tetrahedron 1975, 31, 1963-1967 10.1016/0040-4020(75)87060-8
8. D'Ambrosio, M.; Guerriero, A.; Pietra, F. Helv. Chim. Acta 1984, 67, 1484-1492 10.1002/hlca.19840670610
9. Lacy, C.; Scheuer, P. J. J. Nat. Prod. 2000, 63 (1) 119-121 10.1021/np9902643
10. Shen, S.; Liu, D.; Wei, C.; Proksch, P.; Lin, W. Bioorg. Med. Chem. 2012, 20 (24) 6924-6928 10.1016/j.bmc.2012.10.014
11. Lee, Y.-J.; Han, S.; Lee, H.-S.; Kang, J. S.; Yun, J.; Sim, C. J.; Shin, H. J.; Lee, J. S. J. Nat. Prod. 2013, 76 (9) 1731-1736 10.1021/np400448y
12. Urban, S.; de Almeida Leone, P.; Carroll, A. R.; Fechner, G. A.; Smith, J.; Hooper, J. N. A.; Quinn, R. J. J. Org. Chem. 1999, 64, 731-735 10.1021/jo981034g
13. Grube, A.; Köck, M. Angew. Chem., Int. Ed. 2007, 46 (13) 2320-2324 10.1002/anie.200604076
14. Teruya, T.; Nakagawa, S.; Koyama, T.; Arimoto, H.; Kita, M.; Uemura, D. Tetrahedron 2004, 60, 6989-6993 10.1016/j.tet.2003.08.083
15. Gao, S.; Wang, Q.; Chen, C. J. Am. Chem. Soc. 2009, 131, 1410-1412 10.1021/ja808110d
16. Skepper, C. K.; Molinski, T. F. J. Org. Chem. 2008, 73, 2592-2597 10.1021/jo702435s
17. Morinaka, B. I.; Molinski, T. F. Org. Lett. 2011, 13, 6388-6341 10.1021/ol2024778
18. Dalisay, D. S.; Molinski, T. F. J. Nat. Prod. 2009, 72, 739-744 10.1021/np900009b
19. Molinski, T. F. Nat. Prod. Rep. 2010, 27, 321-329 10.1039/b920545b
20. Dalisay, D. S.; Rogers, E. W.; Edison, A.; Molinski, T. F. J. Nat. Prod. 2009, 72, 732-738 10.1021/np8007649
21. Molinski, T. F. Curr. Opin. Drug Discovery Dev. 2009, 12, 197-206
22. Kozminski, W.; Nanz, D. J. Magn. Reson. 2000, 142, 294-299 10.1006/jmre.1999.1939
23. Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866-876 10.1021/jo981810k
24. Sergeyev, N. M.; Sergeyeva, N. D.; Raynes, W. T. Magn. Reson. Chem. 1994, 32, 381-385 10.1002/mrc.1260320702
25. Buchner, W.; Scheutzow, D. Org. Magn. Reson. 1975, 7, 615-616 10.1002/mrc.1270071212
26. Aliev, A. E.; Harris, K. D. M. Magn. Reson. Chem. 1993, 31, 54-57 10.1002/mrc.1260310111
27. Sergeyev, N. M.; Sandor, P.; Sergeyeva, N. D.; Raynes, W. T. J. Magn. Reson., Ser. A 1995, 115, 174-182 10.1006/jmra.1995.1164
28. Foris, A. Magn. Reson. Chem. 2000, 38, 813-819 10.1002/1097-458X(200010)38:10<813::AID-MRC669>3.0.CO;2-W
29. Hu, D. X.; Seidl, F. J.; Bucher, C.; Burns, N. Z. J. Am. Chem. Soc. 2015, 137, 3795-3798 10.1021/jacs.5b01384
30. Raynes, W. T.; Grayson, M.; Sergeyev, N. M.; Sergeyeva, N. D. Chem. Phys. Lett. 1994, 226, 433-439 10.1016/0009-2614(94)00781-0
31. Poppe, L.; van Halbeek, H. Magn. Reson. Chem. 1991, 29, 848-851 10.1002/mrc.1260290816
32. NMR Periodic Table. http://www.bruker-nmr.de/guide/eNMR/chem/Cl.html.
33. 35Cl isotope ratio in ocean waters (but not ground water) is uniform and invariant. The primary standard ′halite′, NIST SRM 975, is 0.31977 ± 0.00081 2, Shields, W. S.; Murphy, T. J.; Garner, E. L.; Dibeler, V. H. J. Am. Chem. Soc. 1962, 84, 1519-1522 10.1021/ja00868a001
34. An accurately calibrated secondary standard, derived from seawater from a different location (ISL 354), differs only slightly from the former (σ0.39 ± 0.05‰ 2); see Xiao, Y. K.; Zhou, Y.; Wang, Q.; Wei, H.; Liu, W.; Eastoe, C. J. Chem. Geol. 2002, 182, 655-661 10.1016/S0009-2541(01)00349-7
35. Kaupp, M.; Malkin, O. L.; Malkin, V. G. Chem. Phys. Lett. 1997, 265, 55-59 10.1016/S0009-2614(96)01425-X
36. Kurz, M.; Schmieder, P.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1329-1331 10.1002/anie.199113291
37. Kutateladze, A. G.; Mukhina, O. A. J. Org. Chem. 2014, 79, 8397-8406 10.1021/jo501781b
38. Kutateladze, A. G.; Mukhina, O. A. J. Org. Chem. 2015, 80, 5218-25 10.1021/acs.joc.5b00619
39. Wiitala, K. W.; Hoye, T. R.; Cramer, C. J. J. Chem. Theory Comput. 2006, 2, 1085-1092 10.1021/ct6001016
40. Lodewyk, M. W.; Siebert, M. R.; Tantillo, D. J. Chem. Rev. 2012, 112, 1839-62 10.1021/cr200106v
41. Willoughby, P. H.; Jansma, M. J.; Hoye, T. R. Nat. Protoc. 2014, 9, 643-660 10.1038/nprot.2014.042
42. Barone, G.; Gomez-Paloma, L.; Duca, D.; Silvestri, A.; Riccio, R.; Bifulco, G. Chem.-Eur. J. 2002, 8, 3233-3239 10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO;2-0
43. Barone, G.; Duca, D.; Silvestri, A.; Gomez-Paloma, L.; Riccio, R.; Bifulco, G. Chem.-Eur. J. 2002, 8, 3240-3245 10.1002/1521-3765(20020715)8:14<3240::AID-CHEM3240>3.0.CO;2-G
44. Pankratyev, E. Y.; Tulyabaev, A. R.; Khalilov, L. M. J. Comput. Chem. 2011, 32, 1993-1997 10.1002/jcc.21786
45. Smith, S. G.; Goodman, J. M. J. Am. Chem. Soc. 2010, 132, 12946-12959 10.1021/ja105035r
46. Schneider, C.; Schreier, P.; Humpf, H.-U. Chirality 1997, 9, 563-567 10.1002/(SICI)1520-636X(1997)9:5/6<563::AID-CHIR25>3.0.CO;2-L
47. -). This is supported by literature; the few, well-characterized ′halogenases′ from marine organisms responsible for electrophilic halogenation are all bromoperoxidases, not chloroperoxidases: Butler, A.; Carter-Franklin, J. N. Nat. Prod. Rep. 2004, 21, 180-188 10.1039/b302337k
48. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1972, 11, 129-130 10.1002/anie.197201291
49. Grob, C. A.; Winstein, S. Helv. Chim. Acta 1952, 35, 782-802 10.1002/hlca.19520350315
50. Barton, D. H. R.; Head, A. J. J. Chem. Soc. 1956, 932-937 10.1039/jr9560000932
51. Alt, G. H.; Barton, D. H. R. J. Chem. Soc. 1954, 4284-4294 10.1039/jr9540004284
52. Fernandez, I.; Cossio, F. P.; Sierra, M. A. Chem. Rev. 2009, 109, 6687-6711 10.1021/cr900209c
53. González, A. G.; Derias, J.; Martín, J. D.; Perez, C. Tetrahedron Lett. 1974, 15, 1249-1250 10.1016/S0040-4039(01)82457-6
54. González, A. G.; Darias, J.; Martín, J. D. Tetrahedron Lett. 1973, 14, 2381-2384 10.1016/S0040-4039(01)96225-2
55. Juagdan, E. G.; Kalidindi, R.; Scheuer, P. J. Tetrahedron 1997, 53, 521-528 10.1016/S0040-4020(96)01002-2
56. González, A. G.; Darias, J.; Martín, J. D. Tetrahedron Lett. 1973, 14, 3625-3626 10.1016/S0040-4039(01)86990-2
57. González, A. G.; Martín, J. D.; Martin, V. S.; Norte, M. Tetrahedron Lett. 1979, 20, 2719-2722 10.1016/S0040-4039(01)86397-8
58. Sims, J. J.; Fenical, W.; Wing, R. M.; Radlick, P. J. Am. Chem. Soc. 1973, 95, 972-972 10.1021/ja00784a083
59. Elsworth, J. F.; Thomson, R. H. J. Nat. Prod. 1989, 52, 893-895 10.1021/np50064a044
60. (Hattori, K.; Kawasaki, C. J. Pharm. Soc. Jpn. 1937, 57, 115, 588)