Intramolecular α-glucosaminidation: Synthesis of mycothiol

Organic Letters

Volumn 12, Issue 11, 2010, Pages 2630-2633

  Ajayi, Kehinde ^a   Thakur, Vinay V ^a   Lapo, Robert C ^a   Knapp, Spencer ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; GLUCOSAMINE; GLYCOPEPTIDE; INOSITOL; MYCOTHIOL; THIOGLYCOSIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION; MYCOBACTERIUM TUBERCULOSIS; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYSTEINE; GLUCOSAMINE; GLYCOPEPTIDES; GLYCOSYLATION; INOSITOL; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM; THIOGLYCOSIDES;

EID: 77953004058     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1008334     Document Type: Article

References (63)

1. Barry, C. E., III; Duncan, K. Drug Discovery Today 2004, 1, 491-496
2. Xie, Z.; Siddiqi, N.; Rubin, E. J. Antimicrob. Agents Chemother. 2005, 49, 4778-4780
3. Isolation
4. Newton, G. L.; Fahey, R. C.; Cohen, G.; Aharonowitz, Y. J. Bacteriol. 1993, 175, 2734-2742
5. Sakuda, S.; Zhou, Z.-Y.; Yamada, Y. Biosci. Biotechnol. Biochem. 1994, 58, 1347-1348
6. Spies, H. S. C.; Steenkamp, D. J. Eur. Biochem. 1994, 224, 203-213
7. Newton, G. L.; Arnold, K.; Prince, M. S.; Sherrill, C.; delCardayré, S. B.; Aharonowitz, Y.; Cohen, G.; Davies, J.; Fahey, R. C.; Davis, C. J. Bacteriol. 1996, 178, 1990-1995
8. Recent reviews
9. Jothivasan, V. K.; Hamilton, C. J. Nat. Prod. Rep. 2008, 25, 1091-1117
10. Newton, G. L.; Buchmeier, N.; Fahey, R. C. Microbiol. Mol. Biol. Rev. 2008, 72, 471-494
11. Mycothiol biosynthesis
12. Bornemann, C.; Jardine, M. A.; Spies, H. S. C.; Steenkamp, D. J. Biochem. J. 1997, 325, 623-629
13. Newton, G. L.; Koledin, T.; Gorovitz, B.; Rawat, M.; Fahey, R. C.; Av-Gay, Y. J. Bacteriol. 2003, 185, 3476-3479
14. Newton, G. L.; Ta, P.; Bzymek, K. P.; Fahey, R. C. J. Biol. Chem. 2006, 281, 33910-33920
15. Newton, G. L.; Av-Gay, Y.; Fahey, R. C. J. Bacteriol. 2000, 182, 6958-6963
16. Koledin, T.; Newton, G. L.; Fahey, R. C. Arch. Microbiol. 2002, 178, 331-337
17. Sareen, D.; Steffak, M.; Newton, G. L.; Fahey, R. C. Biochemistry 2002, 41, 6885-6890
18. Mycothiol mediated detoxification
19. Newton, G. L.; Av-Gay, Y.; Fahey, R. C. Biochemistry 2000, 39, 10739-10746
20. Park, J.-H.; Roe, J.-H. Mol. Microbiol. 2008, 68, 861-870
21. Steffak, M.; Newton, G. L.; Av-Gay, Y.; Fahey, R. C. Biochemistry 2003, 42, 12067-12076
22. Payne, D. J.; Gwynn, M. N.; Holmes, D. J.; Pompliano, D. L. Nat. Rev. Drug Discovery 2007, 6, 29-40
23. MSH synthesis
24. Lee, S.; Rosazza, J. P. N. Org. Lett. 2004, 6, 365-368
25. Bimane conjugate of MSH
26. Jardine, M. A.; Spies, H. S. C.; Nkambule, C. M.; Gammon, D. W.; Steenkamp, D. J. J. Bioorg. Med. Chem. 2002, 10, 875-881
27. Nichols, G. M.; Kovac, P.; Bewley, C. A. J. Am. Chem. Soc. 2002, 124, 3492-3493
28. Knapp, S.; Gonzalez, S.; Myers, D. S.; Eckman, L. L.; Bewley, C. A. Org. Lett. 2002, 4, 4337-4339
29. MSH analogues
30. Gammon, D. W.; Hunter, R.; Steenkamp, D. J.; Mudzunga, T. T. Bioorg. Med. Chem. Lett. 2003, 13, 2045-2049
31. Knapp, S.; Amorelli, B.; Darout, E.; Ventocilla, C. C.; Goldman, L. M.; Huhn, R. A.; Minnihan, E. C. J. Carbohydr. Chem. 2005, 24, 103-130
32. Metaferia, B. B.; Ray, S.; Smith, J. A.; Bewley, C. A. Bioorg. Med. Chem. Lett. 2007, 17, 444-447
33. Metaferia, B. B.; Fetterolf, B. J.; Shazad-ul-Hussan, S.; Moravec, M.; Smith, J. A.; Ray, S.; Gutierrz-Lugo, M.-T.; Bewley, C. A. J. Med. Chem. 2007, 50, 6326-6336
34. Stewart, M. J. G.; Jothivasan, V. K.; Rowan, A. S.; Wagg, J.; Hamilton, C. J. Org. Biomol. Chem. 2008, 6, 385-390
35. Recent glucosaminidation methods
36. Li, Y.; Yang, Y.; Yu, B. Tetrahedron Lett. 2008, 49, 3604-3608
37. Mensah, E. A.; Nguyen, H. M. J. Am. Chem. Soc. 2009, 131, 8778-8780
38. Yang, Y.; Li, Y.; Yu, B. J. Am. Chem. Soc. 2009, 131, 12076-12077
39. Intramolecular glycosylation
40. Barresi, F.; Hindsgaul, O. J. Am. Chem. Soc. 1991, 113, 9376-9377
41. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087-1088
42. Bols, M. J. Chem. Soc., Chem. Commun. 1992, 913-914
43. Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1765-1767
44. Fairbanks, A. J. Synlett 2003, 1945-1958
45. Cumpstey, I. Carbohydr. Res. 2008, 343, 1553-1573
46. Portions of this work have appeared
47. Ajayi, K. Ph.D. Dissertation, Rutgers University, Piscataway, NJ, 2010.
48. Lapo, R. C.; Knapp, S. Abstracts of Papers, 225th Meeting of the American Chemical Society; American Chemical Society: Washington, DC, 2003; p U260, Meeting Abstract 56-CARB.
49. Bergmann, M.; Zervas, L. Chem. Ber. 1931, 64, 973-980
50. Nyasse, B.; Grehn, L.; Maia, H. L. S.; Monteiro, L. S.; Ragnarsson, U. J. Org. Chem. 1999, 64, 7135-7139
51. Pozsgay, V.; Jennings, H. J. Tetrahedron Lett. 1987, 28, 1375-1376
52. Schwesinger, R.; Willaredt, J.; Schlemper, H.; Keller, M.; Schmitt, D.; Fritz, H. Chem. Ber. 1994, 127, 2435-2454
53. Trost, B. M.; Murayama, E. J. Am. Chem. Soc. 1981, 103, 6529-6530
54. Chavez, F.; Sherry, A. D. J. Org. Chem. 1989, 54, 2990-2992
55. Massy, D. J. R.; Wyss, P. Helv. Chim. Acta 1990, 73, 1037-1057
56. Baker, G. R.; Billington, D. C.; Gani, D. Tetrahedron 1991, 47, 3895-3908
57. Koto, S.; Hirooka, M.; Yoshida, T.; Takenaka, K.; Asai, C.; Nagamitsu, T.; Sakuma, H.; Sakurai, M.; Masuzawa, S.; Komiya, M.; Sato, T.; Zen, S.; Yago, K.; Tomonaga, F. Bull. Chem. Soc. Jpn. 2000, 73, 2521-2529
58. Jones, J. H.; Thomas, D. W.; Wood, M. E. Synth. Commun. 1986, 16, 1607-1610
59. Corey, E. J.; Bock, M. G. Tetrahedron Lett. 1975, 16, 3269-3270
60. A 1 → 5 iminium-induced hydride shift
61. Wolfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Angew. Chem., Int. Ed. Engl. 1999, 38, 200-201
62. Wolfling, J.; Frank, E.; Schneider, G.; Tietze, L. F. Eur. J. Org. Chem. 2004, 90-100
63. Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 1702-1706