Self-assembling urea-based peptidomimetics: A simple one-step synthesis and crystal structure of core β-alanyl ureylene retro-bispeptides (MeO-A(aa)-[NH-CO-NH]-CH2-CH2-CO-NH-A(aa)-OMe; A(aa) = amino acid A)

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4659-4662

  Ranganathan, Darshan ^a   Kurur, Sunita ^a   Madhusudanan, K P ^b   Karle, Isabella L ^c  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

^c NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE DERIVATIVE; UREA;

ARTICLE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0030912790     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00960-X     Document Type: Article

References (26)

1. For reviews see; Spatola, A. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983, Vol. 7, p.267 and Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699 and references cited therein.
2. For reviews see; Spatola, A. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins; Weinstein, B. Ed.; Marcel Dekker: New York, 1983, Vol. 7, p.267 and Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699 and references cited therein.
3. Rizo J.; Gierasch, L.M. Annu. Rev. Biochem. 1992, 61, 387 and references cited therein.
4. Hirschmann, R. Angew. Chem. Int. Ed. Engl. 1991, 30, 1278; Beeley, N. Tib Tech. 1994, 12, 213; Kazmierski, W. M. Tib Tech. 1994, 12, 216.
5. Hirschmann, R. Angew. Chem. Int. Ed. Engl. 1991, 30, 1278; Beeley, N. Tib Tech. 1994, 12, 213; Kazmierski, W. M. Tib Tech. 1994, 12, 216.
6. Hirschmann, R. Angew. Chem. Int. Ed. Engl. 1991, 30, 1278; Beeley, N. Tib Tech. 1994, 12, 213; Kazmierski, W. M. Tib Tech. 1994, 12, 216.
7. For reviews see: Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1; Lawrence, D.S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229; and ref 1.
8. For reviews see: Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1; Lawrence, D.S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229; and ref 1.
9. For reviews see: Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1; Lawrence, D.S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229; and ref 1.
10. Several efficient solid phase synthesis of ureas (Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055; Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 2583) and oligoureas (Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 907; Kim, J-M.; Bi, Y.; Paikoff; S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305; Burgess, K. Ibarzo, J.; Linthicum, D. S.; Russel, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J.; J. Am. Chem. Soc. 1997, 119, 1556) have recently been reported.
11. Several efficient solid phase synthesis of ureas (Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055; Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 2583) and oligoureas (Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 907; Kim, J-M.; Bi, Y.; Paikoff; S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305; Burgess, K. Ibarzo, J.; Linthicum, D. S.; Russel, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J.; J. Am. Chem. Soc. 1997, 119, 1556) have recently been reported.
12. Several efficient solid phase synthesis of ureas (Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055; Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 2583) and oligoureas (Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 907; Kim, J-M.; Bi, Y.; Paikoff; S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305; Burgess, K. Ibarzo, J.; Linthicum, D. S.; Russel, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J.; J. Am. Chem. Soc. 1997, 119, 1556) have recently been reported.
13. Several efficient solid phase synthesis of ureas (Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055; Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 2583) and oligoureas (Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 907; Kim, J-M.; Bi, Y.; Paikoff; S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305; Burgess, K. Ibarzo, J.; Linthicum, D. S.; Russel, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J.; J. Am. Chem. Soc. 1997, 119, 1556) have recently been reported.
14. Several efficient solid phase synthesis of ureas (Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1994, 35, 4055; Hutchins, S. M.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 2583) and oligoureas (Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem. Int. Ed. Engl. 1995, 34, 907; Kim, J-M.; Bi, Y.; Paikoff; S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305; Burgess, K. Ibarzo, J.; Linthicum, D. S.; Russel, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J.; J. Am. Chem. Soc. 1997, 119, 1556) have recently been reported.
15. Lam, P. Y. S.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; Ru, Y.; Bacheler, L. T.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Wong, Y. N.; Chang, C.-H.; Weber, P. C.; Jackson, D. A.; Sharpe, T. R.; Erickson-Viitanen, S. Science, 1994, 263, 380.
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17. Zhao, X.; Chang, Y. L.; Fowler, F.W.; Lauher, J. W. J. Am Chem. Soc. 1990, 112, 6627; Chang, Y. L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 599; Nowick, J.S; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith; E. M.; Ziller, J. W. J. Am Chem. Soc. 1995, 117, 89.
18. Zhao, X.; Chang, Y. L.; Fowler, F.W.; Lauher, J. W. J. Am Chem. Soc. 1990, 112, 6627; Chang, Y. L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 599; Nowick, J.S; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith; E. M.; Ziller, J. W. J. Am Chem. Soc. 1995, 117, 89.
19. Zhao, X.; Chang, Y. L.; Fowler, F.W.; Lauher, J. W. J. Am Chem. Soc. 1990, 112, 6627; Chang, Y. L.; West, M. A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 599; Nowick, J.S; Abdi, M.; Bellamo, K. A.; Love, J. A.; Martinez, E. J.; Noronha, G.; Smith; E. M.; Ziller, J. W. J. Am Chem. Soc. 1995, 117, 89.
20. Ranganathan D.; Kurur, S. Tetrahedron Lett. 1997, 38, 1265-1268
21. 2) and the reaction mixture left stirred at room temperature for 48 h. After normal peptide work up, the residue obtained was either directly crystallized from ethyl acetate/ hexane or purified through a small column of silica gel using ethyl acetate/ hexane as solvents to afford ureylene peptides in ∼ 25-30% yields.
22. DCC is also known to mediate Lossen rearrangement of hydroxamic acids under neutral conditions (Hoare, D. G.; Olson, A.; Koshland, Jr., D. E. J. Am Chem. Soc. 1968, 90, 1638; Bergman, J.; Lindstrom, J.-O.; Abrahamsson, J.; Hadler, E. Tetrahedron Lett. 1976, 3615.
23. DCC is also known to mediate Lossen rearrangement of hydroxamic acids under neutral conditions (Hoare, D. G.; Olson, A.; Koshland, Jr., D. E. J. Am Chem. Soc. 1968, 90, 1638; Bergman, J.; Lindstrom, J.-O.; Abrahamsson, J.; Hadler, E. Tetrahedron Lett. 1976, 3615.
24. The modest yield may be attributed to the formation of some intractable polymeric material.
25. +.
26. NLO activity was measured (powder method) by detection with a photomultiplier of 532 nm light generated from powder materials. Samples were held between two glass plates and set in an optical sphere. They were irradiated with a pulsed Nd: YAG laser at 1064 nm (11ns, 400 mJ/ pulse).