Mimics of L-rhamnose: Anomeric spirohydantoins and diketopiperazines - Approaches to novel N-linked glycopeptides of rhamnofuranose

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 387-390

  Estevez, Juan C ^a   Smith, Martin D ^a   Lane, Alexandra L ^b   Crook, Sarah ^b   Watkin, David J ^b   Besra, Gurdyal S ^c   Brennan, Patrick J ^c   Nash, Robert J ^d   Fleet, George W J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c Immunology and Pathology   (United States)

^d ABERYSTWYTH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; HYDANTOIN DERIVATIVE; PIPERAZINEDIONE; SPIRO COMPOUND;

ARTICLE; CARBOHYDRATE SYNTHESIS; CELL WALL; DRUG SYNTHESIS; MYCOBACTERIUM; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030039825     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00013-4     Document Type: Article

References (24)

1. J. C. Estevez, J. Saunders, G. S. Besra, P. J. Brennan, R. J. Nash and G. W. J. Fleet, preceding paper.
2. R. C. Glen, G. R. Martin, A. P. Hill, R. M. Hyde, P. M. Woollard, J. A. Salmon, J. Buckingham and A. D. Roberston, J. Med. Chem., 1995, 38, 3566.
3. M. Adamczeski, A. R. Reed and P. Crews, J. Nat. Prod. 1995, 58, 201; C. J. Barrow, L. L. Musza and R. Cooper, Bioorg. Med. Chem. Lett., 1995, 5, 377; C. Prasad, Peptides, 1995, 16, 151.
4. M. Adamczeski, A. R. Reed and P. Crews, J. Nat. Prod. 1995, 58, 201; C. J. Barrow, L. L. Musza and R. Cooper, Bioorg. Med. Chem. Lett., 1995, 5, 377; C. Prasad, Peptides, 1995, 16, 151.
5. M. Adamczeski, A. R. Reed and P. Crews, J. Nat. Prod. 1995, 58, 201; C. J. Barrow, L. L. Musza and R. Cooper, Bioorg. Med. Chem. Lett., 1995, 5, 377; C. Prasad, Peptides, 1995, 16, 151.
6. M. Nakajima, K. Itoi, Y. Takamatsu, T. Kinoshita, T. Okazaki, K. Kawakubo, M. Shindou, T. Honma, M. Tohjigamori and T. Haneishi, J. Antibiot., 1991, 44, 293; H. Haruyama, T. Takayama, T. Kinoshita, M. Kondo, M. Nakajima and T. Haneishi, J. Chem. Soc., Perkin Trans. 1, 1991, 1637.
7. M. Nakajima, K. Itoi, Y. Takamatsu, T. Kinoshita, T. Okazaki, K. Kawakubo, M. Shindou, T. Honma, M. Tohjigamori and T. Haneishi, J. Antibiot., 1991, 44, 293; H. Haruyama, T. Takayama, T. Kinoshita, M. Kondo, M. Nakajima and T. Haneishi, J. Chem. Soc., Perkin Trans. 1, 1991, 1637.
8. S. Takahasi, M. Nakajima, T. Kinoshita, H. Haruyama, S. Sugai, T. Honma, S. Sato and T. Haneishi, ACS Symp. Ser., 1994, 551, 74.
9. T. M. Krulle, K. A. Watson, M. Gregoriuo, L. N. Johnson, S. Crook, D. J. Watkin, R. C. Griffiths, R. J. Nash, K. E. Tsitsanou, S. E. Zographos, N. Oikonomakos and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 8291.
10. J. W. Burton, J. C. Son, A. J. Fairbanks, S. S. Choi, H. Taylor, D. J. Watkin, B. G. Winchester and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 6119.
11. 3), 66.12, 80.76, 81.01, 81.88 (4xd, 4x-CH-), 92.47, 112.40 (2xs, 2x-C-), 168.84 (s, C=O).
12. 3), 64.54, 79.77, 80.25, 82.16 (4xd, 4x-CH), 92.46, 113.23 (2xs, 2x-C-), 156.97, 174.27 (2xs, 2xC=O).
13. The structures of 9 and 13 have been firmly established by X-ray crystallographic analysis; details will be provided in the full paper.
14. 3), 66.46, 72.32, 75.48, 86.23 (4xd, 4x-CH), 93.53 (s, -C-), 158.28, 176.26 (2xs, 2xC=O).
15. 3), 66.03, 80.21, 82.61, 83.06 (4xd, 4x-CH-), 128.24, 128.39, 128.71 (3xd, 5xAr-H), 88.69, 114.13, 136.35 (3xs, 3x-C-), 156.87, 169.28, 169.55 (3xs, 3xC=O)
16. 2-), 66.54, 81.80, 82.40, 84.51 (4xd, 4x-CH-), 88.52, 114.46 (2xs, 2x-C-), 166.02, 167.92 (2xs, 2xC=O).
17. 2-), 66.52, 72.69, 75.31, 86.29 (4xd, 4x-CH-), 89.50 (s, -C-), 167.87, 169.25 (2xs, 2xC=O).
18. 3), 65.72, 81.34, 85.60, 87.40 (4xd, 4x-CH-), 93.13, 114.66, 138.10 (3xs, 3x-C-), 128.91, 129.04, 129.49 (3xd, 5xAr-H), 158.98, 168.78, 172.01 (3xs, 3xC=O).
19. 3), 45.89 (t, -CH2-), 65.68, 81.26, 85.66, 89.40 (4xd, 4x-CH-), 92.40, 114.80 (2xs, 2x-C-), 165.21, 167.57 (2xs, 2xC=O).
20. 3), 3.56-4.16 (m, 4H), 4.19 (t, 1H), 4.37 (d, 1H).
21. J. C. Estevez, H. Ardron, M. R. Wormald, D. Brown and G. W. J. Fleet, Tetrahedron Lett., 1994, 35, 8889.
22. A. J. Fairbanks and G. W. J. Fleet, Tetrahedron, 1995, 51, 3881.
23. J. C. Estevez, M. D. Smith, M. R. Wormald, G. S. Besra, P. J. Brennan, R. J. Nash and G. W. J. Fleet, following paper.
24. This work has been supported by the Spanish Education Secretary (MEC-FPU) and the Xunta de Galicia.