Synthesis of spirocyclic glucose-proline hybrids (GlcProHs)

Synlett

Volumn , Issue 20, 2005, Pages 3111-3115

  Zhang, Kaidong ^a   Schweizer, Frank ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Amino acids; Carbohydrates; Glycopeptides; Glycosyl amino acids; Proline

Indexed keywords

AMINO ACID DERIVATIVE; CARBOHYDRATE; EPOXIDE; ESTER; GLUCOSE; GLYCOPEPTIDE; HYDROXYL GROUP; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; GLYCOSYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 29844456172     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922768     Document Type: Article

References (39)

1. Kakinoki, S.; Hirano, Y.; Oka, M. Polym. Bull. (Berlin) 2005, 53, 109.
2. Reddy, K. V. R.; Yedery, R. D.; Aranha, C. Int. J. Antimicrobial Agents 2004, 24, 536.
3. Buku, A.; Faulstich, H.; Wieland, T.; Dabrowski, J. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 2370.
4. Nakajima, T.; Volcani, B. E. Science 1969, 164, 1400.
5. Taylor, S. W.; Waite, J. H.; Ross, M. M.; Shabanowitz, J.; Hunt, D. F. J. Am. Chem. Soc. 1994, 116, 10803.
6. Vitagliano, L.; Berisio, R.; Mazzarella, L.; Zagari, A. Biopolymers 2001, 58, 459; and references therein.
7. Beausoleil, E.; Lubell, W. D. J. Am. Chem. Soc. 1996, 118, 12902; and references therein.
8. Delaney, N. G.; Madison, V. J. J. Am. Chem. Soc. 1982, 104, 6635.
9. Samanen, J.; Zuber, G.; Bean, J.; Eggleston, D.; Romoff, T.; Kopple, K.; Saunders, M.; Regoli, D. Int. J. Pept. Protein Res. 1990, 35, 501.
10. Quancard, J.; Labonne, A.; Jacquot, Y.; Chassaing, G.; Lavielle, S.; Karoyan, P. J. Org. Chem. 2004, 69, 7940.
11. Che, Y.; Marshall, G. R. J. Org. Chem. 2004, 69, 9030; and references therein.
12. Tam, J. P.; Miao, Z. J. Am. Chem. Soc. 1999, 121, 9013; and references therein.
13. Cavelier, F.; Vivet, B.; Martinez, J.; Aubry, A.; Didierjean, C.; Vicherat, A.; Marraud, M. J. Am. Chem. Soc. 2002, 124, 2917; and references therein.
14. Sharma, R.; Lubell, W. D. J. Org. Chem. 1996, 61, 202; and references therein.
15. Jeannotte, G.; Lubell, W. D. J. Org. Chem. 2004, 69, 4656.
16. (a) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451.
17. (b) Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.
18. (c) Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163.
19. Koep, S.; Gais, H.-J.; Raabe, R. J. Am. Chem. Soc. 2003, 125, 13243; and references cited therein.
20. For selected examples of bicyclic proline analogues incorporated into bioactive peptides, see: (a) Cluzeau, J.; Lubell, W. D. Biopolym. Pept. Sci. 2005, 80, 98.
21. (b) Blankley, C. J.; Kaltenbronn, J. S.; DeJohn, D. E.; Wener, A.; Bennett, L. R.; Bobowski, G.; Krolls, U.; Johnson, D. R.; Pearlman, W. M.; Hoefle, M. L. J. Med. Chem. 1987, 30, 992.
22. (c) Dumy, P.; Keller, M.; Ryan, D. E.; Rohwedder, B.; Wöhr, T.; Mutter, M. J. Am. Chem. Soc. 1997, 119, 918.
23. (d) Li, W.; Moeller, K. D. J. Am. Chem. Soc. 1996, 118, 10106.
24. For recent reviews on the synthesis and applications of sugar amino acid hybrids and related materials, see: (a) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395.
25. (b) Schweizer, F. Angew. Chem. Int. Ed. 2002, 41, 230.
26. For recent reviews on the use of sugar amino acids as peptidomimetics, see: (c) Gruner, S. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491.
27. (d) Chakraborty, T. K.; Ghosh, S.; Jayaprakash, J. Curr. Med. Chem. 2002, 9, 421.
28. Grotenbreg, G. M.; Timmer, M. S. M.; Llamas-Saiz, A. L.; Verdoes, M.; Van der Marel, G. A.; van Raaij, M. J.; Overkleeft, H. S.; Overhand, M. J. Am. Chem. Soc. 2004, 126, 3444.
29. Chakraborty, T. K.; Jayaprakash, S.; Diwan, P. V.; Nagaraj, R.; Jampani, S. R. B.; Kunwar, A. C. J. Am. Chem. Soc. 1998, 120, 12962.
30. It has been reported that substitution of D-proline by cis-3-hydroxy-D-proline (HypC3-OH) in the sequence Boc-Leu-Pro-Gly-Leu-NHMe resulted in novel pseudo β-turn-like nine-membered ring structure involving an intramolecular LeuNH → HypC3-OH hydrogen bond.
31. Prior to this publication, a report on a five-membered spirocyclic fructose-based proline analogue appeared: Cipolla, L.; Redaelli, C.; Nicotra, F. Lett. Drug Des. Discov. 2005, 2, 291.
32. Stott, K.; Stonehouse, J.; Keeler, J.; Hwang, T. L.; Shaka, A. J. J. Am. Chem. Soc. 1995, 117, 4199.
33. 2 provides 1 in 95% yield on a multi-gram scale; see: Gueyrard, D.; Haddoub, R.; Salem, A.; Bacar, N. S.; Goekjian, P. G. Synlett 2005, 520.
34. +: 800.3793; found: 800.3791.
35. +: 308.1340; found: 308.1343.
36. 24 experiment showed interproton effects to H-5 (0.65% NOE) and H-7 (0.4% NOE) measured relative to the singlet H-2 signal. This is consistent with the epoxide structure 2.
37. Unreacted starting material was recovered in over 90% yield together with trace amounts of the corresponding amines and amides that were identified by HPLC-MS.
38. A 40 ms gaussian pulse with a 560 ms mixing time was used.
39. 3 (128 mg, 1.95 mmol), followed by 98% AcOH (39 μL, 0.65 mmol).