Design and synthesis of a novel cyclo-β-tetrapeptide

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2629-2632

  Sutton, Peter W ^a   Bradley, Adrian ^a   Elsegood, Mark R J ^b   Farràs, Jaume ^a   Jackson, Richard F W ^b   Romea, Pedro ^a   Urpí, Fèlix ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

Amino acids and derivatives; Lactams; Macrocycles; X Ray crystal structures

Indexed keywords

AMINO ACID; LACTAM; MACROCYCLIC COMPOUND; TETRAPEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CONFORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTON TRANSPORT; X RAY;

EID: 0033605911     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00234-8     Document Type: Article

References (27)

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12. Calculations have been carried on a SGI Power Indigo-2 workstation using both SYBYL (Clark, M.; Cramer III, R. D.; van Opdensch, N. J. Comput. Chem. 1989, 10, 982) and MM2 (for a review see: Burket, U.; Allinger, N. L. "Molecular mechanics", ACS Monograph 177, American Chemical Society, Washington D.C., 1982) force fields as implemented in Spartan 4.1/5.0(Wavefunction, Inc.). Osawa algorithm (Osawa, E. J. J. Am. Chem. Soc. 1989, 111, 8950) was used for conformational search incyclic systems.
13. Calculations have been carried on a SGI Power Indigo-2 workstation using both SYBYL (Clark, M.; Cramer III, R. D.; van Opdensch, N. J. Comput. Chem. 1989, 10, 982) and MM2 (for a review see: Burket, U.; Allinger, N. L. "Molecular mechanics", ACS Monograph 177, American Chemical Society, Washington D.C., 1982) force fields as implemented in Spartan 4.1/5.0(Wavefunction, Inc.). Osawa algorithm (Osawa, E. J. J. Am. Chem. Soc. 1989, 111, 8950) was used for conformational search incyclic systems.
14. Calculations have been carried on a SGI Power Indigo-2 workstation using both SYBYL (Clark, M.; Cramer III, R. D.; van Opdensch, N. J. Comput. Chem. 1989, 10, 982) and MM2 (for a review see: Burket, U.; Allinger, N. L. "Molecular mechanics", ACS Monograph 177, American Chemical Society, Washington D.C., 1982) force fields as implemented in Spartan 4.1/5.0(Wavefunction, Inc.). Osawa algorithm (Osawa, E. J. J. Am. Chem. Soc. 1989, 111, 8950) was used for conformational search incyclic systems.
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17. All new compounds have spectroscopical and analytical data consistent with the assigned structure.
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19. Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243. Also see: Coste, J.; Frérott, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437 (PyBroP). Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397 (HOAt).
20. Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243. Also see: Coste, J.; Frérott, E.; Jouin, P. J. Org. Chem. 1994, 59, 2437 (PyBroP). Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397 (HOAt).
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23. This compound had been previously prepared according to the Arndt-Eistert procedure: Bankowski, K.; Misicka, A.; Barth, T.; Slaninova, J. Collect. Czech. Chem. Commun. 1989, 54, 2795. Ondetti, M. A.; Engel, S. L. J. Med. Chem. 1975, 18, 761.
24. This compound had been previously prepared according to the Arndt-Eistert procedure: Bankowski, K.; Misicka, A.; Barth, T.; Slaninova, J. Collect. Czech. Chem. Commun. 1989, 54, 2795. Ondetti, M. A.; Engel, S. L. J. Med. Chem. 1975, 18, 761.
25. -3. Programs: Bruker SMART ana SAINT for diffractometer control and frame integration (Bruker Analytical X-Ray Instruments, Madison, WI, 1994), Bruker SHELXTL for structure solution, refinement and molecular graphics (G. M. Sheldrick, SHELXTL manual, version 5, Bruker Analytical X-Ray Instruments, Madison, WI, 1994) and local programs.
26. For very recent reviews, see: Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Gennari, C.; Nestler, H. P.; Piarulli U.; Salom, B. Liebigs Ann./Recueil 1997, 637.
27. For very recent reviews, see: Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Gennari, C.; Nestler, H. P.; Piarulli U.; Salom, B. Liebigs Ann./Recueil 1997, 637.