Operationally convenient, efficient asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylene dimerization of chiral glycine equivalents with dichloromethane

Tetrahedron

Volumn 62, Issue 26, 2006, Pages 6412-6419

  Soloshonok, Vadim A ^a   Yamada, Takeshi ^a,b   Ueki, Hisanori ^a   Moore, Anna M ^a   Cook, Tanner K ^a   Arbogast, Kelsey L ^a   Soloshonok, Anatolii V ^a   Martin, Collin H ^a   Ohfune, Yasufumi ^b  

^a UNIVERSITY OF OKLAHOMA   (United States)

^b Osaka Prefecture University   (Japan)

Author keywords

Asymmetric synthesis; Bis amino acid; Chiral glycine equivalents; Methylene dimerization

Indexed keywords

4 AMINOGLUTAMIC ACID DERIVATIVE; CARBENE; DICHLOROMETHANE; GLUTAMIC ACID DERIVATIVE; GLYCINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; DIMERIZATION; ENANTIOMER; PRIORITY JOURNAL;

EID: 33646804903     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.023     Document Type: Article

References (74)

1. Ward J.B. Pharmacol. Ther. 25 (1984) 327-369 and references cited therein
2. Cox R.J. Nat. Prod. Rep. 13 (1996) 29-43
3. Galili G. Plant Cell 7 (1995) 899-906
4. Bugg T.D.H., and Walsh C.T. Nat. Prod. Rep. 9 (1992) 199-215
5. Patte J.-C. In: Hermann K.M., and Sommerville R.L. (Eds). Amino Acids: Biosynthesis and Genetic Regulation (1983), Adison-Wesley, Reading, MA 213-218
6. For the importance of conformationally constrained peptides in the design of low-molecular weight therapeutic agents and for elucidation of structure-activity relationships, see:
7. Hruby V.J. Life Sci. 31 (1982) 189-199
8. Hruby V.J., Al-Obeidi F., and Kazmierski W.M. Biochem. J. 268 (1990) 249-262
9. Hruby V.J. Biopolymers 33 (1993) 1073-1082
10. Hruby V.J., Li G., Haskell-Luevano C., and Shenderovich M.D. Biopolymers 43 (1997) 219-266
11. Hruby V.J. Acc. Chem. Res. 34 (2001) 389-397
12. Hruby V.J. Nat. Rev. Drug Discov. 1 (2002) 847-858
13. For recent papers on the application of bis-AA cyclization motive in peptide design, see:
14. Di Costanzo L., Geremia S., Randaccio L., Ichino T., Yanagihara R., Yamada T., Marasco D., Lombardi A., and Pavone V. J. Chem. Soc., Dalton Trans. 5 (2003) 787-792
15. McNamara L.M.A., Andrews M.J.I., Mitzel F., Siligardi G., and Tabor A.B. J. Org. Chem. 66 (2001) 4585-4594
16. Maricic S., Ritzen A., Berg U., and Frejd T. Tetrahedron 57 (2001) 6523-6529
17. Reichwein J.F., Versluis C., and Liskamp R.M.J. J. Org. Chem. 65 (2000) 6187-6195
18. Reichwein J.F., Wels B., Kruijtzer J.A.W., Versluis C., and Liskamp R.M. Angew. Chem., Int. Ed. 38 (1999) 3684-3687
19. Piscopio A.D., Miller J.F., and Koch K. Tetrahedron 55 (1999) 8189-8198
20. Blackwell H.E., and Grubbs R.H. Angew. Chem., Int. Ed. 37 (1998) 3281-3284
21. Miller S.J., Blackwell H.E., and Grubbs R.H. J. Am. Chem. Soc. 118 (1996) 9606-9614
22. Fairlie D.P., Abbenante G., and March D.R. Curr. Med. Chem. 2 (1995) 654-686
23. The rapidly growing list of amino acids isolated from various natural sources makes the terms unnatural, unusual, noncoded or nonproteinogenic amino acids, which are most frequently used in the literature, dependent on the success of the specific scientific achievements. For instance, amino acids containing the most xenobiotic element fluorine have been shown to be synthesized by microorganisms (see Ref. 7). Therefore, the time independent term tailor-made, meaning rationally designed/synthesized amino acids with presupposed physical, chemical, 3D-structural, and biological features, in the absence of a better definition, seems to be a more appropriate use for such amino acids.
24. Fluorine-Containing Amino Acids. In: Kukhar' V.P., and Soloshonok V.A. (Eds). Synthesis and Properties (1994), Wiley, Chichester, UK and references cited therein
25. For recent leading publications on the preparation of various types of bis-AA, see:
26. Ferreira P.M.T., Maia H.L.S., and Monteiro L.S. Tetrahedron Lett. 44 (2003) 2137-2139
27. Mazaleyrat J.-P., Wright K., Azzini M.-V., Gaucher A., and Wakselman M. Tetrahedron Lett. 44 (2003) 1741-1745
28. Ferioli F., Piccinelli F., Porzi G., and Sandri S. Tetrahedron: Asymmetry 13 (2002) 1181-1187
29. Paradisi F., Piccinelli F., Porzi G., and Sandri S. Tetrahedron: Asymmetry 13 (2002) 497-502
30. Ami E., Rajesh S., Wang J., Kimura T., Hayashi Y., Kiso Y., and Ishida T. Tetrahedron Lett. 43 (2002) 2931-2934
31. Roberts J.L., and Chan C. Tetrahedron Lett. 43 (2002) 7679-7682
32. Sutherland A., and Vederas J.C. Chem. Commun. (2002) 224-225
33. Efskind J., Romming C., and Undheim K. J. Chem. Soc., Perkin Trans. 1 (2001) 2697-2703
34. Acharya A.N., Ostresh J.M., and Houghten R.A. J. Comb. Chem. 3 (2001) 578-589
35. Lygo B., Crosby J., and Peterson J.A. Tetrahedron 57 (2001) 6447-6453
36. Lygo B. Tetrahedron Lett. 40 (1999) 1389-1392
37. Lygo B., Crosby J., and Peterson J.A. Tetrahedron Lett. 40 (1999) 1385-1388
38. Lange M., and Undheim K. Tetrahedron 54 (1998) 5337-5344
39. For recent leading publications on 2,7-diaminosuberic acid and its derivatives, used as dicarba cystine isosteres in the peptide design, see:
40. Hoven G.B., Efskind J., Romming C., and Undheim K. J. Org. Chem. 67 (2002) 2459-2463
41. Hernandez N., and Martin V.S. J. Org. Chem. 66 (2001) 4934-4938
42. Aguilera B., Wolf B.L., Nieczypor P., Rutjes F.P.J.T., Overkleeft H.S., van Hest J.C.M., Schoemaker H.E., Wang B., Mol J.C., Fuerstner A., Overhand M., van der Marel G.A., and van Boom J.H. J. Org. Chem. 66 (2001) 3584-3589
43. Hiebl J., Kollmann H., Rovenszky F., and Winkler K. J. Org. Chem. 64 (1999) 1947-1952
44. Soloshonok V.A. Curr. Org. Chem. 6 (2002) 341-364
45. Soloshonok V.A., Cai C., and Hruby V.J. Tetrahedron Lett. 41 (1999) 135-139
46. Soloshonok V.A., Cai C., Hruby V.J., Meervelt L.V., and Yamazaki T. J. Org. Chem. 65 (2000) 6688-6696
47. For the protocol recently developed by our group for highly diastereoselective, organic base-catalyzed, room temperature Michael addition reactions see:
48. Soloshonok V.A., Cai C., and Hruby V.J. Org. Lett. 2 (2000) 747-750
49. Soloshonok V.A., Cai C., and Hruby V.J. Angew. Chem., Int. Ed. 39 (2000) 2172-2175
50. Cai C., Soloshonok V.A., and Hruby V.J. J. Org. Chem. 66 (2001) 1339-1350
51. Soloshonok V.A., Ueki H., Ellis T.K., Yamada T., and Ohfune Y. Tetrahedron Lett. 46 (2005) 1107-1110
52. Soloshonok V.A., Cai C., Yamada T., Ueki H., Ohfune Y., and Hruby V.J. J. Am. Chem. Soc. 127 (2005) 15296-15303
53. Jullian N., Brabet I., Pin J.-P., and Acher F.C. J. Med. Chem. 42 (1999) 1546-1555
54. Costantino G., Macchiarulo A., and Pellicciari R. J. Med. Chem. 42 (1999) 2816-2827
55. Conti P., De Amici M., De Sarro G., Rizzo M., Stensbol T.B., Braeuner-Osborne H., Madsen U., Toma L., and De Micheli C. J. Med. Chem. 42 (1999) 4099
56. Olverman H.J., Jones A.W., MeWett K.N., and Watkins J.C. Neuroscience 26 (1988) 17-31
57. Zygmunt W.A., Evans R.L., and Stavely H.E. Can. J. Microbiol. 8 (1962) 869-873
58. Tanaka K., and Sawanishi H. Tetrahedron: Asymmetry 9 (1998) 71-77
59. Avenoza A., Cativiela C., Peregrina J.M., and Zurbano M.M. Tetrahedron: Asymmetry 7 (1996) 1555-1558
60. Avenoza A., Cativiela C., Peregrina J.M., and Zurbano M.M. Tetrahedron: Asymmetry 8 (1997) 863-871
61. Arakawa Y., Goto T., Kawase K., and Yoshifuji S. Chem. Pharm. Bull. 43 (1995) 535-536
62. Arakawa Y., Goto T., Kawase K., and Yoshifuji S. Chem. Pharm. Bull. 46 (1998) 674-680
63. Krasnov V.P., Zhdanova E.A., Korolyova M.A., Bukrina I.M., Kodess M.I., Kravtsov V.K., and Biyushkin V.N. Russ. Chem. Bull. 46 (1997) 319-323
64. Kabat M.M. Tetrahedron Lett. 42 (2001) 7521-7524
65. Eberson L. Acta Chem. Scand. 12 (1958) 314-323
66. Belokon Y.N., Chernoglazova N.I., Batsanov A.S., Garbalinskaya N.S., Bakhmutov V.I., Struchkov Y.T., and Belikov V.M. Izv. Akad. Nauk SSSR, Ser. Khim. 4 (1987) 852-857
67. The primed configurations apply to 4-aminoglutamic acid and unprimed to the proline moieties.
68. For a preliminary communication see;. Taylor S.M., Yamada T., Ueki H., and Soloshonok V.A. Tetrahedron Lett. 45 (2004) 9159-9162
69. O'Donnell M.J., and Plot R.L. J. Org. Chem. 47 (1982) 2663-2666
70. For practical, large-scale syntheses of chiral complexes (S)-2 and (S)-11, see:. Ueki H., Ellis T.K., Martin C.H., Bolene S.B., Boettiger T.U., and Soloshonok V.A. J. Org. Chem. 68 (2003) 7104-7107
71. Ellis T.K., Martin C.H., Tsai G.M., Ueki H., and Soloshonok V.A. J. Org. Chem. 68 (2003) 6208-6214
72. For practical, large-scale syntheses of achiral complex 13, see:. Ueki H., Ellis T.K., Martin C.H., and Soloshonok V.A. Eur. J. Org. Chem. (2003) 1954-1957
73. Considering the significant high diastereoselectivity obtained in these reactions, it was of interest to study the asymmetric version of this methylene dimerization using achiral complex 15 and chiral phase-transfer catalyst. Investigation of this catalytic asymmetric methylene dimerization is currently under study and the results obtained will be reported in due course.
74. Soloshonok V.A., Ueki H., and Ellis T.K. Tetrahedron Lett. 46 (2005) 941-944